MiMeDB: Showing metabocard for Cholylvaline (MMDBc0057225)

Microbial

Human

Co-metabolite

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2022-11-10 23:33:25 UTC

Update Date

2024-04-30 20:56:33 UTC

Metabolite ID

MMDBc0057225

Metabolite Identification

Common Name

Cholylvaline

Description

Cholylvaline belongs to a class of molecules known as bile acid-amino acid conjugates. These are bile acid conjugates that consist of a primary bile acid such as cholic acid, doxycholic acid and chenodeoxycholic acid, conjugated to an amino acid. Cholylvaline consists of the bile acid cholic acid conjugated to the amino acid Valine conjugated at the C24 acyl site.Bile acids play an important role in regulating various physiological systems, such as fat digestion, cholesterol metabolism, vitamin absorption, liver function, and enterohepatic circulation through their combined signaling, detergent, and antimicrobial mechanisms (PMID: 34127070 ). Bile acids also act as detergents in the gut and support the absorption of fats through the intestinal membrane. These same properties allow for the disruption of bacterial membranes, thereby allowing them to serve a bacteriocidal or bacteriostatic function. In humans (and other mammals) bile acids are normally conjugated with the amino acids glycine and taurine by the liver. This conjugation catalyzed by two liver enzymes, bile acid CoA ligase (BAL) and bile acid CoA: amino acid N-acyltransferase (BAT). Glycine and taurine bound BAs are also referred to as bile salts due to their decreased pKa and complete ionization resulting in these compounds being present as anions in vivo. Unlike glycine and taurine-conjugated bile acids, these recently discovered bile acids, such as Cholylvaline, are produced by the gut microbiota, making them secondary bile acids (PMID: 32103176 ) or microbially conjugated bile acids (MCBAs) (PMID: 34127070 ). Evidence suggests that these bile acid-amino acid conjugates are produced by microbes belonging to Clostridia species (PMID: 32103176 ). These unusual bile acid-amino acid conjugates are found in higher frequency in patients with inflammatory bowel disease (IBD), cystic fibrosis (CF) and in infants (PMID: 32103176 ). Cholylvaline appears to act as an agonist for the farnesoid X receptor (FXR) and it can also lead to reduced expression of bile acid synthesis genes (PMID: 32103176 ). It currently appears that microbially conjugated bile acids (MCBAs) or amino acid-bile acid conjugates are only conjugated to cholic acid, deoxycholic acid and chenodeoxycholic acid (PMID: 34127070 ). It has been estimated that if microbial conjugation of bile acids is very promiscuous and occurs for all potential oxidized, epimerized, and dehydroxylated states of each hydroxyl group present on cholic acid (C3, C7, C12) in addition to ring orientation, the total number of potential human bile acid conjugates could be over 2800 (PMID: 34127070 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652308302119132D          

 36 39  0  0  0  0            999 V2000
    9.8532   -0.3707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0431   -0.2148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7730    0.5647    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5030   -0.8385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6929   -0.6825    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1528   -1.3062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4228   -2.0857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3426   -1.1503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8026   -1.7739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9924   -1.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4523   -2.2416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7224   -0.8385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9330   -0.5987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9170    0.2261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6966    0.4962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0175    1.2562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5198    1.9141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7012    1.8121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8408    2.6742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6594    2.7762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9804    3.5362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7990    3.6383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1200    4.3983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.8362    1.3583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3339    0.7003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0130   -0.0597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5107   -0.7177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1943   -0.1618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6205   -0.8681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7730   -1.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.2330   -2.2416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
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 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
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 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
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 25 26  1  0  0  0  0
 20 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 16 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 12 32  1  0  0  0  0
 15 32  1  0  0  0  0
 32 33  1  0  0  0  0
  4 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
M  END

HMDB0242380
     RDKit          3D
Cholylvaline
 85 88  0  0  0  0  0  0  0  0999 V2000
    8.7569   -0.1095   -0.6956 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1114   -0.1185    0.6642 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1529   -0.0755    1.7533 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2510   -1.3502    0.8768 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2253   -1.2983   -0.1760 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8743   -1.0227    0.0708 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4910   -0.7990    1.2469 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8905   -0.9883   -1.0191 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4997   -0.6008   -0.4737 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4844   -0.5748   -1.5625 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3928   -1.9583   -2.1677 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2431    0.1508   -1.3679 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5509    1.6201   -1.1051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4746    2.0796   -0.0722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5580    1.0501   -0.2540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6070    1.0071    0.7823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3982    2.2902    0.9058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5845    3.3932    0.9018 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4550    2.4562   -0.1384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3005    1.2412   -0.3316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7471    1.5914   -0.3167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3989    1.6431    1.0167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6353    0.9537    1.0290 O   0  0  0  0  0  0  0  0  0  0  0  0
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    7.7808   -3.4883   -0.0923 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.8402    2.2858    1.9482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1109    4.1672    0.5717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9834    2.7991   -1.0820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1020    3.3167    0.1849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0876    0.8611   -1.3791 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.0980    2.1088    2.6730 H   0  0  0  0  0  0  0  0  0  0  0  0
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    8.7653   -3.3610    2.5695 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
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 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
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 19 20  1  0
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 24 25  1  0
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 29 30  1  0
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 30 32  1  0
 32 33  1  0
  4 34  1  0
 34 35  2  0
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  1 38  1  0
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  2 40  1  0
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  3 42  1  0
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 24 71  1  0
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 29 78  1  0
 29 79  1  0
 30 80  1  0
 31 81  1  0
 33 82  1  0
 33 83  1  0
 33 84  1  0
 36 85  1  0
M  END


  Mrv1652308302119132D          

 36 39  0  0  0  0            999 V2000
    9.8532   -0.3707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0431   -0.2148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7730    0.5647    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5030   -0.8385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6929   -0.6825    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1528   -1.3062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4228   -2.0857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3426   -1.1503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8026   -1.7739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9924   -1.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4523   -2.2416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7224   -0.8385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9330   -0.5987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9170    0.2261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6966    0.4962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0175    1.2562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5198    1.9141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7012    1.8121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8408    2.6742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6594    2.7762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9804    3.5362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7990    3.6383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1200    4.3983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2967    2.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9758    2.2203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1571    2.1183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6549    1.4603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8362    1.3583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3339    0.7003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0130   -0.0597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5107   -0.7177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1943   -0.1618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6205   -0.8681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7730   -1.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5832   -1.7739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2330   -2.2416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 20 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 16 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 12 32  1  0  0  0  0
 15 32  1  0  0  0  0
 32 33  1  0  0  0  0
  4 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0057225

> <DATABASE_NAME>
MIME

> <SMILES>
CC(C)C(NC(=O)CCC(C)C1CCC2C3C(O)CC4CC(O)CCC4(C)C3CC(O)C12C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C29H49NO6/c1-15(2)26(27(35)36)30-24(34)9-6-16(3)19-7-8-20-25-21(14-23(33)29(19,20)5)28(4)11-10-18(31)12-17(28)13-22(25)32/h15-23,25-26,31-33H,6-14H2,1-5H3,(H,30,34)(H,35,36)

> <INCHI_KEY>
WVFDPCYTNIXGHI-UHFFFAOYSA-N

> <FORMULA>
C29H49NO6

> <MOLECULAR_WEIGHT>
507.712

> <EXACT_MASS>
507.355988302

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
85

> <JCHEM_AVERAGE_POLARIZABILITY>
58.60804999516811

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-methyl-2-(4-{5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl}pentanamido)butanoic acid

> <ALOGPS_LOGP>
2.16

> <JCHEM_LOGP>
2.8334706806666676

> <ALOGPS_LOGS>
-4.65

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.241921525062665

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.9196501474383454

> <JCHEM_PKA_STRONGEST_BASIC>
-0.0909511260399225

> <JCHEM_POLAR_SURFACE_AREA>
127.09000000000002

> <JCHEM_REFRACTIVITY>
137.0823

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.13e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-methyl-2-(4-{5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl}pentanamido)butanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0242380
     RDKit          3D
Cholylvaline
 85 88  0  0  0  0  0  0  0  0999 V2000
    8.7569   -0.1095   -0.6956 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1114   -0.1185    0.6642 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1529   -0.0755    1.7533 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2510   -1.3502    0.8768 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2253   -1.2983   -0.1760 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8743   -1.0227    0.0708 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4910   -0.7990    1.2469 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8905   -0.9883   -1.0191 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4997   -0.6008   -0.4737 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4844   -0.5748   -1.5625 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3928   -1.9583   -2.1677 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2431    0.1508   -1.3679 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5509    1.6201   -1.1051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4746    2.0796   -0.0722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5580    1.0501   -0.2540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6070    1.0071    0.7823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3982    2.2902    0.9058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5845    3.3932    0.9018 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4550    2.4562   -0.1384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3005    1.2412   -0.3316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7471    1.5914   -0.3167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3989    1.6431    1.0167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6353    0.9537    1.0290 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5799    1.2161    2.1741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5895    0.1515    1.9326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9679    0.0947    0.5755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6210   -1.1283   -0.1054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4809   -0.1887    0.5852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1565   -0.9275   -0.6971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7084   -1.3153   -0.8158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5426   -2.4862   -0.0722 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7508   -0.2242   -0.3311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2010   -0.6822    0.9623 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0181   -2.6068    0.8025 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7808   -3.4883   -0.0923 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0339   -2.8993    1.6960 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9856   -0.0229   -1.4884 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2653   -1.0830   -0.8689 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4525    0.7577   -0.7153 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4815    0.8029    0.7189 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7843   -0.6671    2.6104 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2696    0.9925    2.0707 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1584   -0.4383    1.3925 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7132   -1.2354    1.8334 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5447   -1.4832   -1.1636 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2172   -0.2023   -1.7604 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8693   -2.0017   -1.4672 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6463    0.3087    0.0963 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3098   -1.4131    0.2866 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0185    0.0133   -2.4014 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3013   -2.2517   -2.7324 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5587   -2.0715   -2.8856 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2567   -2.7268   -1.3765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3227    0.1210   -2.3539 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4600    2.2056   -2.0678 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5776    1.8016   -0.7700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0286    2.0793    0.9382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7555    3.0991   -0.4311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9882    1.2697   -1.2661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1229    0.9018    1.7946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8402    2.2858    1.9482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1109    4.1672    0.5717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9834    2.7991   -1.0820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1020    3.3167    0.1849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0876    0.8611   -1.3791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3637    0.8933   -0.9585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8402    2.5746   -0.8709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6978    2.7184    1.2027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0626    1.0782    1.9120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0980    2.1088    2.6730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3016    0.8675    2.9739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0688   -0.8343    2.2268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7575    0.2315    2.6947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7239   -0.9539    0.0932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4007   -2.0606    0.4221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5109   -1.1216   -1.1848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3503   -0.9590    1.4041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7208   -1.9074   -0.6880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5366   -0.4153   -1.6045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5496   -1.5064   -1.9180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0256   -3.1105   -0.6741 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6309   -0.0812    1.3664 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0816   -1.7637    0.8969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9969   -0.6796    1.7363 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7653   -3.3610    2.5695 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 30 32  1  0
 32 33  1  0
  4 34  1  0
 34 35  2  0
 34 36  1  0
 32 12  1  0
 32 15  1  0
 28 16  1  0
 26 20  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
  2 40  1  0
  3 41  1  0
  3 42  1  0
  3 43  1  0
  4 44  1  0
  5 45  1  0
  8 46  1  0
  8 47  1  0
  9 48  1  0
  9 49  1  0
 10 50  1  0
 11 51  1  0
 11 52  1  0
 11 53  1  0
 12 54  1  0
 13 55  1  0
 13 56  1  0
 14 57  1  0
 14 58  1  0
 15 59  1  0
 16 60  1  0
 17 61  1  0
 18 62  1  0
 19 63  1  0
 19 64  1  0
 20 65  1  0
 21 66  1  0
 21 67  1  0
 22 68  1  0
 23 69  1  0
 24 70  1  0
 24 71  1  0
 25 72  1  0
 25 73  1  0
 27 74  1  0
 27 75  1  0
 27 76  1  0
 28 77  1  0
 29 78  1  0
 29 79  1  0
 30 80  1  0
 31 81  1  0
 33 82  1  0
 33 83  1  0
 33 84  1  0
 36 85  1  0
M  END

HEADER    PROTEIN                                 30-AUG-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-AUG-21         0                                  
HETATM    1  O   UNK     0      18.393  -0.692   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      16.880  -0.401   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      16.376   1.054   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      15.872  -1.565   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      14.360  -1.274   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      13.352  -2.438   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      13.856  -3.893   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      11.840  -2.147   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.831  -3.311   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.319  -3.020   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.311  -4.184   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.815  -1.565   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.342  -1.118   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.312   0.422   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.767   0.926   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.366   2.345   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.437   3.573   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.909   3.383   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       9.036   4.992   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.564   5.182   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.163   6.601   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.691   6.791   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      13.291   8.210   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      13.621   5.563   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      13.021   4.145   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.493   3.954   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.422   2.726   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.894   2.535   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      11.823   1.307   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      11.224  -0.111   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      12.153  -1.340   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       9.696  -0.302   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      10.492  -1.621   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      16.376  -3.020   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      17.889  -3.311   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      15.368  -4.184   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   34                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   32                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   32                                                  
CONECT   16   15   17   28                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   26                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   20   27   28                                             
CONECT   27   26                                                            
CONECT   28   26   16   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   12   15   33                                             
CONECT   33   32                                                            
CONECT   34    4   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

COMPND    HMDB0242380
HETATM    1  C1  UNL     1       8.757  -0.109  -0.696  1.00  0.00           C  
HETATM    2  C2  UNL     1       8.111  -0.119   0.664  1.00  0.00           C  
HETATM    3  C3  UNL     1       9.153  -0.075   1.753  1.00  0.00           C  
HETATM    4  C4  UNL     1       7.251  -1.350   0.877  1.00  0.00           C  
HETATM    5  N1  UNL     1       6.225  -1.298  -0.176  1.00  0.00           N  
HETATM    6  C5  UNL     1       4.874  -1.023   0.071  1.00  0.00           C  
HETATM    7  O1  UNL     1       4.491  -0.799   1.247  1.00  0.00           O  
HETATM    8  C6  UNL     1       3.891  -0.988  -1.019  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.500  -0.601  -0.474  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.484  -0.575  -1.562  1.00  0.00           C  
HETATM   11  C9  UNL     1       1.393  -1.958  -2.168  1.00  0.00           C  
HETATM   12  C10 UNL     1       0.243   0.151  -1.368  1.00  0.00           C  
HETATM   13  C11 UNL     1       0.551   1.620  -1.105  1.00  0.00           C  
HETATM   14  C12 UNL     1      -0.475   2.080  -0.072  1.00  0.00           C  
HETATM   15  C13 UNL     1      -1.558   1.050  -0.254  1.00  0.00           C  
HETATM   16  C14 UNL     1      -2.607   1.007   0.782  1.00  0.00           C  
HETATM   17  C15 UNL     1      -3.398   2.290   0.906  1.00  0.00           C  
HETATM   18  O2  UNL     1      -2.585   3.393   0.902  1.00  0.00           O  
HETATM   19  C16 UNL     1      -4.455   2.456  -0.138  1.00  0.00           C  
HETATM   20  C17 UNL     1      -5.301   1.241  -0.332  1.00  0.00           C  
HETATM   21  C18 UNL     1      -6.747   1.591  -0.317  1.00  0.00           C  
HETATM   22  C19 UNL     1      -7.399   1.643   1.017  1.00  0.00           C  
HETATM   23  O3  UNL     1      -8.635   0.954   1.029  1.00  0.00           O  
HETATM   24  C20 UNL     1      -6.580   1.216   2.174  1.00  0.00           C  
HETATM   25  C21 UNL     1      -5.590   0.152   1.933  1.00  0.00           C  
HETATM   26  C22 UNL     1      -4.968   0.095   0.576  1.00  0.00           C  
HETATM   27  C23 UNL     1      -5.621  -1.128  -0.105  1.00  0.00           C  
HETATM   28  C24 UNL     1      -3.481  -0.189   0.585  1.00  0.00           C  
HETATM   29  C25 UNL     1      -3.156  -0.927  -0.697  1.00  0.00           C  
HETATM   30  C26 UNL     1      -1.708  -1.315  -0.816  1.00  0.00           C  
HETATM   31  O4  UNL     1      -1.543  -2.486  -0.072  1.00  0.00           O  
HETATM   32  C27 UNL     1      -0.751  -0.224  -0.331  1.00  0.00           C  
HETATM   33  C28 UNL     1      -0.201  -0.682   0.962  1.00  0.00           C  
HETATM   34  C29 UNL     1       8.018  -2.607   0.802  1.00  0.00           C  
HETATM   35  O5  UNL     1       7.781  -3.488  -0.092  1.00  0.00           O  
HETATM   36  O6  UNL     1       9.034  -2.899   1.696  1.00  0.00           O  
HETATM   37  H1  UNL     1       7.986  -0.023  -1.488  1.00  0.00           H  
HETATM   38  H2  UNL     1       9.265  -1.083  -0.869  1.00  0.00           H  
HETATM   39  H3  UNL     1       9.452   0.758  -0.715  1.00  0.00           H  
HETATM   40  H4  UNL     1       7.482   0.803   0.719  1.00  0.00           H  
HETATM   41  H5  UNL     1       8.784  -0.667   2.610  1.00  0.00           H  
HETATM   42  H6  UNL     1       9.270   0.993   2.071  1.00  0.00           H  
HETATM   43  H7  UNL     1      10.158  -0.438   1.393  1.00  0.00           H  
HETATM   44  H8  UNL     1       6.713  -1.235   1.833  1.00  0.00           H  
HETATM   45  H9  UNL     1       6.545  -1.483  -1.164  1.00  0.00           H  
HETATM   46  H10 UNL     1       4.217  -0.202  -1.760  1.00  0.00           H  
HETATM   47  H11 UNL     1       3.869  -2.002  -1.467  1.00  0.00           H  
HETATM   48  H12 UNL     1       2.646   0.309   0.096  1.00  0.00           H  
HETATM   49  H13 UNL     1       2.310  -1.413   0.287  1.00  0.00           H  
HETATM   50  H14 UNL     1       2.019   0.013  -2.401  1.00  0.00           H  
HETATM   51  H15 UNL     1       2.301  -2.252  -2.732  1.00  0.00           H  
HETATM   52  H16 UNL     1       0.559  -2.071  -2.886  1.00  0.00           H  
HETATM   53  H17 UNL     1       1.257  -2.727  -1.377  1.00  0.00           H  
HETATM   54  H18 UNL     1      -0.323   0.121  -2.354  1.00  0.00           H  
HETATM   55  H19 UNL     1       0.460   2.206  -2.068  1.00  0.00           H  
HETATM   56  H20 UNL     1       1.578   1.802  -0.770  1.00  0.00           H  
HETATM   57  H21 UNL     1      -0.029   2.079   0.938  1.00  0.00           H  
HETATM   58  H22 UNL     1      -0.755   3.099  -0.431  1.00  0.00           H  
HETATM   59  H23 UNL     1      -1.988   1.270  -1.266  1.00  0.00           H  
HETATM   60  H24 UNL     1      -2.123   0.902   1.795  1.00  0.00           H  
HETATM   61  H25 UNL     1      -3.840   2.286   1.948  1.00  0.00           H  
HETATM   62  H26 UNL     1      -3.111   4.167   0.572  1.00  0.00           H  
HETATM   63  H27 UNL     1      -3.983   2.799  -1.082  1.00  0.00           H  
HETATM   64  H28 UNL     1      -5.102   3.317   0.185  1.00  0.00           H  
HETATM   65  H29 UNL     1      -5.088   0.861  -1.379  1.00  0.00           H  
HETATM   66  H30 UNL     1      -7.364   0.893  -0.958  1.00  0.00           H  
HETATM   67  H31 UNL     1      -6.840   2.575  -0.871  1.00  0.00           H  
HETATM   68  H32 UNL     1      -7.698   2.718   1.203  1.00  0.00           H  
HETATM   69  H33 UNL     1      -9.063   1.078   1.912  1.00  0.00           H  
HETATM   70  H34 UNL     1      -6.098   2.109   2.673  1.00  0.00           H  
HETATM   71  H35 UNL     1      -7.302   0.867   2.974  1.00  0.00           H  
HETATM   72  H36 UNL     1      -6.069  -0.834   2.227  1.00  0.00           H  
HETATM   73  H37 UNL     1      -4.757   0.231   2.695  1.00  0.00           H  
HETATM   74  H38 UNL     1      -6.724  -0.954   0.093  1.00  0.00           H  
HETATM   75  H39 UNL     1      -5.401  -2.061   0.422  1.00  0.00           H  
HETATM   76  H40 UNL     1      -5.511  -1.122  -1.185  1.00  0.00           H  
HETATM   77  H41 UNL     1      -3.350  -0.959   1.404  1.00  0.00           H  
HETATM   78  H42 UNL     1      -3.721  -1.907  -0.688  1.00  0.00           H  
HETATM   79  H43 UNL     1      -3.537  -0.415  -1.605  1.00  0.00           H  
HETATM   80  H44 UNL     1      -1.550  -1.506  -1.918  1.00  0.00           H  
HETATM   81  H45 UNL     1      -1.026  -3.110  -0.674  1.00  0.00           H  
HETATM   82  H46 UNL     1       0.631  -0.081   1.366  1.00  0.00           H  
HETATM   83  H47 UNL     1       0.082  -1.764   0.897  1.00  0.00           H  
HETATM   84  H48 UNL     1      -0.997  -0.680   1.736  1.00  0.00           H  
HETATM   85  H49 UNL     1       8.765  -3.361   2.570  1.00  0.00           H  
CONECT    1    2   37   38   39
CONECT    2    3    4   40
CONECT    3   41   42   43
CONECT    4    5   34   44
CONECT    5    6   45
CONECT    6    7    7    8
CONECT    8    9   46   47
CONECT    9   10   48   49
CONECT   10   11   12   50
CONECT   11   51   52   53
CONECT   12   13   32   54
CONECT   13   14   55   56
CONECT   14   15   57   58
CONECT   15   16   32   59
CONECT   16   17   28   60
CONECT   17   18   19   61
CONECT   18   62
CONECT   19   20   63   64
CONECT   20   21   26   65
CONECT   21   22   66   67
CONECT   22   23   24   68
CONECT   23   69
CONECT   24   25   70   71
CONECT   25   26   72   73
CONECT   26   27   28
CONECT   27   74   75   76
CONECT   28   29   77
CONECT   29   30   78   79
CONECT   30   31   32   80
CONECT   31   81
CONECT   32   33
CONECT   33   82   83   84
CONECT   34   35   35   36
CONECT   36   85
END

HMDB0242380
     RDKit          3D
Cholylvaline
 85 88  0  0  0  0  0  0  0  0999 V2000
    8.7569   -0.1095   -0.6956 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1114   -0.1185    0.6642 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1529   -0.0755    1.7533 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2510   -1.3502    0.8768 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2253   -1.2983   -0.1760 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8743   -1.0227    0.0708 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4910   -0.7990    1.2469 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8905   -0.9883   -1.0191 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4997   -0.6008   -0.4737 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4844   -0.5748   -1.5625 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3928   -1.9583   -2.1677 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2431    0.1508   -1.3679 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5509    1.6201   -1.1051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4746    2.0796   -0.0722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5580    1.0501   -0.2540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6070    1.0071    0.7823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3982    2.2902    0.9058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5845    3.3932    0.9018 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4550    2.4562   -0.1384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3005    1.2412   -0.3316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7471    1.5914   -0.3167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3989    1.6431    1.0167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6353    0.9537    1.0290 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5799    1.2161    2.1741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5895    0.1515    1.9326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9679    0.0947    0.5755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6210   -1.1283   -0.1054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4809   -0.1887    0.5852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1565   -0.9275   -0.6971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7084   -1.3153   -0.8158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5426   -2.4862   -0.0722 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7508   -0.2242   -0.3311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2010   -0.6822    0.9623 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0181   -2.6068    0.8025 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7808   -3.4883   -0.0923 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0339   -2.8993    1.6960 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9856   -0.0229   -1.4884 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2653   -1.0830   -0.8689 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4525    0.7577   -0.7153 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4815    0.8029    0.7189 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7843   -0.6671    2.6104 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2696    0.9925    2.0707 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1584   -0.4383    1.3925 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7132   -1.2354    1.8334 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5447   -1.4832   -1.1636 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2172   -0.2023   -1.7604 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8693   -2.0017   -1.4672 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6463    0.3087    0.0963 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3098   -1.4131    0.2866 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0185    0.0133   -2.4014 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3013   -2.2517   -2.7324 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5587   -2.0715   -2.8856 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2567   -2.7268   -1.3765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3227    0.1210   -2.3539 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4600    2.2056   -2.0678 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5776    1.8016   -0.7700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0286    2.0793    0.9382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7555    3.0991   -0.4311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9882    1.2697   -1.2661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1229    0.9018    1.7946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8402    2.2858    1.9482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1109    4.1672    0.5717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9834    2.7991   -1.0820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1020    3.3167    0.1849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0876    0.8611   -1.3791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3637    0.8933   -0.9585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8402    2.5746   -0.8709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6978    2.7184    1.2027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0626    1.0782    1.9120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0980    2.1088    2.6730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3016    0.8675    2.9739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0688   -0.8343    2.2268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7575    0.2315    2.6947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7239   -0.9539    0.0932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4007   -2.0606    0.4221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5109   -1.1216   -1.1848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3503   -0.9590    1.4041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7208   -1.9074   -0.6880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5366   -0.4153   -1.6045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5496   -1.5064   -1.9180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0256   -3.1105   -0.6741 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6309   -0.0812    1.3664 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0816   -1.7637    0.8969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9969   -0.6796    1.7363 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7653   -3.3610    2.5695 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 30 32  1  0
 32 33  1  0
  4 34  1  0
 34 35  2  0
 34 36  1  0
 32 12  1  0
 32 15  1  0
 28 16  1  0
 26 20  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
  2 40  1  0
  3 41  1  0
  3 42  1  0
  3 43  1  0
  4 44  1  0
  5 45  1  0
  8 46  1  0
  8 47  1  0
  9 48  1  0
  9 49  1  0
 10 50  1  0
 11 51  1  0
 11 52  1  0
 11 53  1  0
 12 54  1  0
 13 55  1  0
 13 56  1  0
 14 57  1  0
 14 58  1  0
 15 59  1  0
 16 60  1  0
 17 61  1  0
 18 62  1  0
 19 63  1  0
 19 64  1  0
 20 65  1  0
 21 66  1  0
 21 67  1  0
 22 68  1  0
 23 69  1  0
 24 70  1  0
 24 71  1  0
 25 72  1  0
 25 73  1  0
 27 74  1  0
 27 75  1  0
 27 76  1  0
 28 77  1  0
 29 78  1  0
 29 79  1  0
 30 80  1  0
 31 81  1  0
 33 82  1  0
 33 83  1  0
 33 84  1  0
 36 85  1  0
M  END

Synonyms

Value	Source
Cholylvaline	HMDB
Val-Cho	HMDB
Val-CA	HMDB
Valocholic acid	HMDB
Valocholate	HMDB

Molecular Formula

C₂₉H₄₉NO₆

Average Mass

507.712

Monoisotopic Mass

507.355988302

IUPAC Name

3-methyl-2-(4-{5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl}pentanamido)butanoic acid

Traditional Name

3-methyl-2-(4-{5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl}pentanamido)butanoic acid

CAS Registry Number

Not Available

SMILES

CC(C)C(NC(=O)CCC(C)C1CCC2C3C(O)CC4CC(O)CCC4(C)C3CC(O)C12C)C(O)=O

InChI Identifier

InChI=1S/C29H49NO6/c1-15(2)26(27(35)36)30-24(34)9-6-16(3)19-7-8-20-25-21(14-23(33)29(19,20)5)28(4)11-10-18(31)12-17(28)13-22(25)32/h15-23,25-26,31-33H,6-14H2,1-5H3,(H,30,34)(H,35,36)

InChI Key

WVFDPCYTNIXGHI-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glycinated bile acids and derivatives. Glycinated bile acids and derivatives are compounds with a structure characterized by the presence of a glycine linked to a bile acid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Glycinated bile acids and derivatives

Alternative Parents

Substituents

Glycinated bile acid
Trihydroxy bile acid, alcohol, or derivatives
Hydroxy bile acid, alcohol, or derivatives
7-hydroxysteroid
Hydroxysteroid
12-hydroxysteroid
3-hydroxysteroid
Valine or derivatives
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
Alpha-amino acid or derivatives
Fatty acyl
N-acyl-amine
Fatty amide
Cyclic alcohol
Secondary carboxylic acid amide
Secondary alcohol
Carboxamide group
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.011 g/L	ALOGPS
logP	2.16	ALOGPS
logP	2.83	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	3.92	ChemAxon
pKa (Strongest Basic)	-0.091	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	127.09 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	137.08 m³·mol⁻¹	ChemAxon
Polarizability	58.61 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01vo-0005910000-fb286d95db4e2f34a028	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00dl-1409800000-c259f7990c4fe0c867e1	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0kdr-8931000000-0668c835d1ea339c867b	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0000590000-8c5f6bac98bf0d392720	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-052r-0108920000-d59561ebf039e7bd103f	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0080-1009100000-979f2f8ec1a02f775e9e	2021-10-12	View Spectrum

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (eluted)	2025-10-24	230.4
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-24	128.7
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-24	576.0
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-24	606.6
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-24	568.2
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (eluted)	2025-10-24	159.3
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	2999.9
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (void)	2025-10-24	139.7
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-24	316.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	503.1
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	206.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	160.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	203.5
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	94.7
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	251.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	243.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	436.2
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-24	1617.3
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-24	1004.2

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	Cholylvaline_TMS_1	CC(C)C(NC(=O)CCC(C)C1CCC2C3C(O[Si](C)(C)C)CC4CC(O)CCC4(C)C3CC(O)C12C)C(=O)O	standard non polar	2025-10-24	1493.03
Gas Chromatography	Cholylvaline_TMS_2	CC(C)C(NC(=O)CCC(C)C1CCC2C3C(O)CC4CC(O[Si](C)(C)C)CCC4(C)C3CC(O)C12C)C(=O)O	standard non polar	2025-10-24	1524.26
Gas Chromatography	Cholylvaline_TMS_3	CC(C)C(NC(=O)CCC(C)C1CCC2C3C(O)CC4CC(O)CCC4(C)C3CC(O[Si](C)(C)C)C12C)C(=O)O	standard non polar	2025-10-24	1821.93
Gas Chromatography	Cholylvaline_TMS_4	CC(C)C(NC(=O)CCC(C)C1CCC2C3C(O)CC4CC(O)CCC4(C)C3CC(O)C12C)C(=O)O[Si](C)(C)C	standard non polar	2025-10-24	1651.23
Gas Chromatography	Cholylvaline_TMS_5	CC(C)C(C(=O)O)N(C(=O)CCC(C)C1CCC2C3C(O)CC4CC(O)CCC4(C)C3CC(O)C12C)[Si](C)(C)C	standard non polar	2025-10-24	2731.27
Gas Chromatography	Cholylvaline_TMS_6	CC(C)C(NC(=O)CCC(C)C1CCC2C3C(O[Si](C)(C)C)CC4CC(O[Si](C)(C)C)CCC4(C)C3CC(O)C12C)C(=O)O	standard non polar	2025-10-24	2208.62
Gas Chromatography	Cholylvaline_TMS_7	CC(C)C(NC(=O)CCC(C)C1CCC2C3C(O[Si](C)(C)C)CC4CC(O)CCC4(C)C3CC(O[Si](C)(C)C)C12C)C(=O)O	standard non polar	2025-10-24	630.147
Gas Chromatography	Cholylvaline_TMS_8	CC(C)C(NC(=O)CCC(C)C1CCC2C3C(O[Si](C)(C)C)CC4CC(O)CCC4(C)C3CC(O)C12C)C(=O)O[Si](C)(C)C	standard non polar	2025-10-24	866.3
Gas Chromatography	Cholylvaline_TMS_9	CC(C)C(C(=O)O)N(C(=O)CCC(C)C1CCC2C3C(O[Si](C)(C)C)CC4CC(O)CCC4(C)C3CC(O)C12C)[Si](C)(C)C	standard non polar	2025-10-24	1845.96
Gas Chromatography	Cholylvaline_TMS_10	CC(C)C(NC(=O)CCC(C)C1CCC2C3C(O)CC4CC(O[Si](C)(C)C)CCC4(C)C3CC(O[Si](C)(C)C)C12C)C(=O)O	standard non polar	2025-10-24	2355.45
Gas Chromatography	Cholylvaline_TMS_11	CC(C)C(NC(=O)CCC(C)C1CCC2C3C(O)CC4CC(O[Si](C)(C)C)CCC4(C)C3CC(O)C12C)C(=O)O[Si](C)(C)C	standard non polar	2025-10-24	1237.99
Gas Chromatography	Cholylvaline_TMS_12	CC(C)C(C(=O)O)N(C(=O)CCC(C)C1CCC2C3C(O)CC4CC(O[Si](C)(C)C)CCC4(C)C3CC(O)C12C)[Si](C)(C)C	standard non polar	2025-10-24	2189.43
Gas Chromatography	Cholylvaline_TMS_13	CC(C)C(NC(=O)CCC(C)C1CCC2C3C(O)CC4CC(O)CCC4(C)C3CC(O[Si](C)(C)C)C12C)C(=O)O[Si](C)(C)C	standard non polar	2025-10-24	2028.5
Gas Chromatography	Cholylvaline_TMS_14	CC(C)C(C(=O)O)N(C(=O)CCC(C)C1CCC2C3C(O)CC4CC(O)CCC4(C)C3CC(O[Si](C)(C)C)C12C)[Si](C)(C)C	standard non polar	2025-10-24	2230.71
Gas Chromatography	Cholylvaline_TMS_15	CC(C)C(C(=O)O[Si](C)(C)C)N(C(=O)CCC(C)C1CCC2C3C(O)CC4CC(O)CCC4(C)C3CC(O)C12C)[Si](C)(C)C	standard non polar	2025-10-24	2400.35
Gas Chromatography	Cholylvaline_TMS_16	CC(C)C(NC(=O)CCC(C)C1CCC2C3C(O[Si](C)(C)C)CC4CC(O[Si](C)(C)C)CCC4(C)C3CC(O[Si](C)(C)C)C12C)C(=O)O	standard non polar	2025-10-24	2786.24
Gas Chromatography	Cholylvaline_TMS_17	CC(C)C(NC(=O)CCC(C)C1CCC2C3C(O[Si](C)(C)C)CC4CC(O[Si](C)(C)C)CCC4(C)C3CC(O)C12C)C(=O)O[Si](C)(C)C	standard non polar	2025-10-24	3137.76
Gas Chromatography	Cholylvaline_TMS_18	CC(C)C(C(=O)O)N(C(=O)CCC(C)C1CCC2C3C(O[Si](C)(C)C)CC4CC(O[Si](C)(C)C)CCC4(C)C3CC(O)C12C)[Si](C)(C)C	standard non polar	2025-10-24	1021.65
Gas Chromatography	Cholylvaline_TMS_19	CC(C)C(NC(=O)CCC(C)C1CCC2C3C(O[Si](C)(C)C)CC4CC(O)CCC4(C)C3CC(O[Si](C)(C)C)C12C)C(=O)O[Si](C)(C)C	standard non polar	2025-10-24	2479.02
Gas Chromatography	Cholylvaline_TMS_20	CC(C)C(C(=O)O)N(C(=O)CCC(C)C1CCC2C3C(O[Si](C)(C)C)CC4CC(O)CCC4(C)C3CC(O[Si](C)(C)C)C12C)[Si](C)(C)C	standard non polar	2025-10-24	2533.08
Gas Chromatography	Cholylvaline_TMS_21	CC(C)C(C(=O)O[Si](C)(C)C)N(C(=O)CCC(C)C1CCC2C3C(O[Si](C)(C)C)CC4CC(O)CCC4(C)C3CC(O)C12C)[Si](C)(C)C	standard non polar	2025-10-24	1454.04
Gas Chromatography	Cholylvaline_TMS_22	CC(C)C(NC(=O)CCC(C)C1CCC2C3C(O)CC4CC(O[Si](C)(C)C)CCC4(C)C3CC(O[Si](C)(C)C)C12C)C(=O)O[Si](C)(C)C	standard non polar	2025-10-24	1499.35
Gas Chromatography	Cholylvaline_TMS_23	CC(C)C(C(=O)O)N(C(=O)CCC(C)C1CCC2C3C(O)CC4CC(O[Si](C)(C)C)CCC4(C)C3CC(O[Si](C)(C)C)C12C)[Si](C)(C)C	standard non polar	2025-10-24	2591.49
Gas Chromatography	Cholylvaline_TMS_24	CC(C)C(C(=O)O[Si](C)(C)C)N(C(=O)CCC(C)C1CCC2C3C(O)CC4CC(O[Si](C)(C)C)CCC4(C)C3CC(O)C12C)[Si](C)(C)C	standard non polar	2025-10-24	2478.29
Gas Chromatography	Cholylvaline_TMS_25	CC(C)C(C(=O)O[Si](C)(C)C)N(C(=O)CCC(C)C1CCC2C3C(O)CC4CC(O)CCC4(C)C3CC(O[Si](C)(C)C)C12C)[Si](C)(C)C	standard non polar	2025-10-24	2112.21
Gas Chromatography	Cholylvaline_TMS_26	CC(C)C(NC(=O)CCC(C)C1CCC2C3C(O[Si](C)(C)C)CC4CC(O[Si](C)(C)C)CCC4(C)C3CC(O[Si](C)(C)C)C12C)C(=O)O[Si](C)(C)C	standard non polar	2025-10-24	1625.44
Gas Chromatography	Cholylvaline_TMS_27	CC(C)C(C(=O)O)N(C(=O)CCC(C)C1CCC2C3C(O[Si](C)(C)C)CC4CC(O[Si](C)(C)C)CCC4(C)C3CC(O[Si](C)(C)C)C12C)[Si](C)(C)C	standard non polar	2025-10-24	2397.24
Gas Chromatography	Cholylvaline_TMS_28	CC(C)C(C(=O)O[Si](C)(C)C)N(C(=O)CCC(C)C1CCC2C3C(O[Si](C)(C)C)CC4CC(O[Si](C)(C)C)CCC4(C)C3CC(O)C12C)[Si](C)(C)C	standard non polar	2025-10-24	2659.58
Gas Chromatography	Cholylvaline_TMS_29	CC(C)C(C(=O)O[Si](C)(C)C)N(C(=O)CCC(C)C1CCC2C3C(O[Si](C)(C)C)CC4CC(O)CCC4(C)C3CC(O[Si](C)(C)C)C12C)[Si](C)(C)C	standard non polar	2025-10-24	2563.06
Gas Chromatography	Cholylvaline_TMS_30	CC(C)C(C(=O)O[Si](C)(C)C)N(C(=O)CCC(C)C1CCC2C3C(O)CC4CC(O[Si](C)(C)C)CCC4(C)C3CC(O[Si](C)(C)C)C12C)[Si](C)(C)C	standard non polar	2025-10-24	1930.49
Gas Chromatography	Cholylvaline_TMS_31	CC(C)C(C(=O)O[Si](C)(C)C)N(C(=O)CCC(C)C1CCC2C3C(O[Si](C)(C)C)CC4CC(O[Si](C)(C)C)CCC4(C)C3CC(O[Si](C)(C)C)C12C)[Si](C)(C)C	standard non polar	2025-10-24	1603.23
Gas Chromatography	Cholylvaline_TMS_1	CC(C)C(NC(=O)CCC(C)C1CCC2C3C(O[Si](C)(C)C)CC4CC(O)CCC4(C)C3CC(O)C12C)C(=O)O	standard polar	2025-10-24	2010.62
Gas Chromatography	Cholylvaline_TMS_2	CC(C)C(NC(=O)CCC(C)C1CCC2C3C(O)CC4CC(O[Si](C)(C)C)CCC4(C)C3CC(O)C12C)C(=O)O	standard polar	2025-10-24	2105.54
Gas Chromatography	Cholylvaline_TMS_3	CC(C)C(NC(=O)CCC(C)C1CCC2C3C(O)CC4CC(O)CCC4(C)C3CC(O[Si](C)(C)C)C12C)C(=O)O	standard polar	2025-10-24	833.318
Gas Chromatography	Cholylvaline_TMS_4	CC(C)C(NC(=O)CCC(C)C1CCC2C3C(O)CC4CC(O)CCC4(C)C3CC(O)C12C)C(=O)O[Si](C)(C)C	standard polar	2025-10-24	2161.49
Gas Chromatography	Cholylvaline_TMS_5	CC(C)C(C(=O)O)N(C(=O)CCC(C)C1CCC2C3C(O)CC4CC(O)CCC4(C)C3CC(O)C12C)[Si](C)(C)C	standard polar	2025-10-24	1610.52
Gas Chromatography	Cholylvaline_TMS_6	CC(C)C(NC(=O)CCC(C)C1CCC2C3C(O[Si](C)(C)C)CC4CC(O[Si](C)(C)C)CCC4(C)C3CC(O)C12C)C(=O)O	standard polar	2025-10-24	1811.41
Gas Chromatography	Cholylvaline_TMS_7	CC(C)C(NC(=O)CCC(C)C1CCC2C3C(O[Si](C)(C)C)CC4CC(O)CCC4(C)C3CC(O[Si](C)(C)C)C12C)C(=O)O	standard polar	2025-10-24	2168.95
Gas Chromatography	Cholylvaline_TMS_8	CC(C)C(NC(=O)CCC(C)C1CCC2C3C(O[Si](C)(C)C)CC4CC(O)CCC4(C)C3CC(O)C12C)C(=O)O[Si](C)(C)C	standard polar	2025-10-24	2931.66
Gas Chromatography	Cholylvaline_TMS_9	CC(C)C(C(=O)O)N(C(=O)CCC(C)C1CCC2C3C(O[Si](C)(C)C)CC4CC(O)CCC4(C)C3CC(O)C12C)[Si](C)(C)C	standard polar	2025-10-24	2419.57
Gas Chromatography	Cholylvaline_TMS_10	CC(C)C(NC(=O)CCC(C)C1CCC2C3C(O)CC4CC(O[Si](C)(C)C)CCC4(C)C3CC(O[Si](C)(C)C)C12C)C(=O)O	standard polar	2025-10-24	2706.41
Gas Chromatography	Cholylvaline_TMS_11	CC(C)C(NC(=O)CCC(C)C1CCC2C3C(O)CC4CC(O[Si](C)(C)C)CCC4(C)C3CC(O)C12C)C(=O)O[Si](C)(C)C	standard polar	2025-10-24	1671.45
Gas Chromatography	Cholylvaline_TMS_12	CC(C)C(C(=O)O)N(C(=O)CCC(C)C1CCC2C3C(O)CC4CC(O[Si](C)(C)C)CCC4(C)C3CC(O)C12C)[Si](C)(C)C	standard polar	2025-10-24	2229.22
Gas Chromatography	Cholylvaline_TMS_13	CC(C)C(NC(=O)CCC(C)C1CCC2C3C(O)CC4CC(O)CCC4(C)C3CC(O[Si](C)(C)C)C12C)C(=O)O[Si](C)(C)C	standard polar	2025-10-24	2222.4
Gas Chromatography	Cholylvaline_TMS_14	CC(C)C(C(=O)O)N(C(=O)CCC(C)C1CCC2C3C(O)CC4CC(O)CCC4(C)C3CC(O[Si](C)(C)C)C12C)[Si](C)(C)C	standard polar	2025-10-24	652.793
Gas Chromatography	Cholylvaline_TMS_15	CC(C)C(C(=O)O[Si](C)(C)C)N(C(=O)CCC(C)C1CCC2C3C(O)CC4CC(O)CCC4(C)C3CC(O)C12C)[Si](C)(C)C	standard polar	2025-10-24	2648.59
Gas Chromatography	Cholylvaline_TMS_16	CC(C)C(NC(=O)CCC(C)C1CCC2C3C(O[Si](C)(C)C)CC4CC(O[Si](C)(C)C)CCC4(C)C3CC(O[Si](C)(C)C)C12C)C(=O)O	standard polar	2025-10-24	2757.18
Gas Chromatography	Cholylvaline_TMS_17	CC(C)C(NC(=O)CCC(C)C1CCC2C3C(O[Si](C)(C)C)CC4CC(O[Si](C)(C)C)CCC4(C)C3CC(O)C12C)C(=O)O[Si](C)(C)C	standard polar	2025-10-24	3611.7
Gas Chromatography	Cholylvaline_TMS_18	CC(C)C(C(=O)O)N(C(=O)CCC(C)C1CCC2C3C(O[Si](C)(C)C)CC4CC(O[Si](C)(C)C)CCC4(C)C3CC(O)C12C)[Si](C)(C)C	standard polar	2025-10-24	4095.85
Gas Chromatography	Cholylvaline_TMS_19	CC(C)C(NC(=O)CCC(C)C1CCC2C3C(O[Si](C)(C)C)CC4CC(O)CCC4(C)C3CC(O[Si](C)(C)C)C12C)C(=O)O[Si](C)(C)C	standard polar	2025-10-24	2355.56
Gas Chromatography	Cholylvaline_TMS_20	CC(C)C(C(=O)O)N(C(=O)CCC(C)C1CCC2C3C(O[Si](C)(C)C)CC4CC(O)CCC4(C)C3CC(O[Si](C)(C)C)C12C)[Si](C)(C)C	standard polar	2025-10-24	2227.64
Gas Chromatography	Cholylvaline_TMS_21	CC(C)C(C(=O)O[Si](C)(C)C)N(C(=O)CCC(C)C1CCC2C3C(O[Si](C)(C)C)CC4CC(O)CCC4(C)C3CC(O)C12C)[Si](C)(C)C	standard polar	2025-10-24	2969.21
Gas Chromatography	Cholylvaline_TMS_22	CC(C)C(NC(=O)CCC(C)C1CCC2C3C(O)CC4CC(O[Si](C)(C)C)CCC4(C)C3CC(O[Si](C)(C)C)C12C)C(=O)O[Si](C)(C)C	standard polar	2025-10-24	792.587
Gas Chromatography	Cholylvaline_TMS_23	CC(C)C(C(=O)O)N(C(=O)CCC(C)C1CCC2C3C(O)CC4CC(O[Si](C)(C)C)CCC4(C)C3CC(O[Si](C)(C)C)C12C)[Si](C)(C)C	standard polar	2025-10-24	2586.04
Gas Chromatography	Cholylvaline_TMS_24	CC(C)C(C(=O)O[Si](C)(C)C)N(C(=O)CCC(C)C1CCC2C3C(O)CC4CC(O[Si](C)(C)C)CCC4(C)C3CC(O)C12C)[Si](C)(C)C	standard polar	2025-10-24	2136.52
Gas Chromatography	Cholylvaline_TMS_25	CC(C)C(C(=O)O[Si](C)(C)C)N(C(=O)CCC(C)C1CCC2C3C(O)CC4CC(O)CCC4(C)C3CC(O[Si](C)(C)C)C12C)[Si](C)(C)C	standard polar	2025-10-24	1584.28
Gas Chromatography	Cholylvaline_TMS_26	CC(C)C(NC(=O)CCC(C)C1CCC2C3C(O[Si](C)(C)C)CC4CC(O[Si](C)(C)C)CCC4(C)C3CC(O[Si](C)(C)C)C12C)C(=O)O[Si](C)(C)C	standard polar	2025-10-24	-78.8711
Gas Chromatography	Cholylvaline_TMS_27	CC(C)C(C(=O)O)N(C(=O)CCC(C)C1CCC2C3C(O[Si](C)(C)C)CC4CC(O[Si](C)(C)C)CCC4(C)C3CC(O[Si](C)(C)C)C12C)[Si](C)(C)C	standard polar	2025-10-24	-104.405
Gas Chromatography	Cholylvaline_TMS_28	CC(C)C(C(=O)O[Si](C)(C)C)N(C(=O)CCC(C)C1CCC2C3C(O[Si](C)(C)C)CC4CC(O[Si](C)(C)C)CCC4(C)C3CC(O)C12C)[Si](C)(C)C	standard polar	2025-10-24	718.577
Gas Chromatography	Cholylvaline_TMS_29	CC(C)C(C(=O)O[Si](C)(C)C)N(C(=O)CCC(C)C1CCC2C3C(O[Si](C)(C)C)CC4CC(O)CCC4(C)C3CC(O[Si](C)(C)C)C12C)[Si](C)(C)C	standard polar	2025-10-24	1639.27
Gas Chromatography	Cholylvaline_TMS_30	CC(C)C(C(=O)O[Si](C)(C)C)N(C(=O)CCC(C)C1CCC2C3C(O)CC4CC(O[Si](C)(C)C)CCC4(C)C3CC(O[Si](C)(C)C)C12C)[Si](C)(C)C	standard polar	2025-10-24	2209.84
Gas Chromatography	Cholylvaline_TMS_31	CC(C)C(C(=O)O[Si](C)(C)C)N(C(=O)CCC(C)C1CCC2C3C(O[Si](C)(C)C)CC4CC(O[Si](C)(C)C)CCC4(C)C3CC(O[Si](C)(C)C)C12C)[Si](C)(C)C	standard polar	2025-10-24	1756.08

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Intestine

Tissue Locations

Intestine

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Intestine	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597

External Links

HMDB ID

HMDB0242380

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

85527347

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Guzior DV, Quinn RA: Review: microbial transformations of human bile acids. Microbiome. 2021 Jun 14;9(1):140. doi: 10.1186/s40168-021-01101-1. [PubMed:34127070 ]
Quinn RA, Melnik AV, Vrbanac A, Fu T, Patras KA, Christy MP, Bodai Z, Belda-Ferre P, Tripathi A, Chung LK, Downes M, Welch RD, Quinn M, Humphrey G, Panitchpakdi M, Weldon KC, Aksenov A, da Silva R, Avila-Pacheco J, Clish C, Bae S, Mallick H, Franzosa EA, Lloyd-Price J, Bussell R, Thron T, Nelson AT, Wang M, Leszczynski E, Vargas F, Gauglitz JM, Meehan MJ, Gentry E, Arthur TD, Komor AC, Poulsen O, Boland BS, Chang JT, Sandborn WJ, Lim M, Garg N, Lumeng JC, Xavier RJ, Kazmierczak BI, Jain R, Egan M, Rhee KE, Ferguson D, Raffatellu M, Vlamakis H, Haddad GG, Siegel D, Huttenhower C, Mazmanian SK, Evans RM, Nizet V, Knight R, Dorrestein PC: Global chemical effects of the microbiome include new bile-acid conjugations. Nature. 2020 Mar;579(7797):123-129. doi: 10.1038/s41586-020-2047-9. Epub 2020 Feb 26. [PubMed:32103176 ]

Showing metabocard for Cholylvaline (MMDBc0057225)

MOL for #<Metabolite:0x00007f9abc815908>

3D MOL for #<Metabolite:0x00007f9abc815908>

3D SDF for #<Metabolite:0x00007f9abc815908>

3D-SDF for #<Metabolite:0x00007f9abc815908>

PDB for #<Metabolite:0x00007f9abc815908>

3D PDB for #<Metabolite:0x00007f9abc815908>

SMILES for #<Metabolite:0x00007f9abc815908>

INCHI for #<Metabolite:0x00007f9abc815908>

Structure for #<Metabolite:0x00007f9abc815908>

3D Structure for #<Metabolite:0x00007f9abc815908>