Showing metabocard for N-Butyrylglycine (MMDBc0000549)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-12-10 18:40:18 UTC
Update Date2024-04-30 19:32:57 UTC
Metabolite IDMMDBc0000549
Metabolite Identification
Common NameN-Butyrylglycine
DescriptionN-Butyrylglycine is an acyl glycine. Acyl glycines are normally minor metabolites of fatty acids. However, the excretion of certain acyl glycines is increased in several inborn errors of metabolism, such as ethylmalonic encephalopathy. In certain cases the measurement of these metabolites in body fluids can be used to diagnose disorders associated with mitochondrial fatty acid beta-oxidation. Acyl glycines are produced through the action of glycine N-acyltransferase (EC 2.3.1.13), which is an enzyme that catalyzes the chemical reaction: acyl-CoA + glycine < -- > CoA + N-acylglycine amino acids composed of glycine substituted at the nitrogen rather than the usual carbon position, resulting in the loss of hydrogen bonding donors. Polymers of these compounds are called Peptoids.
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00005645c9fc4fd0>

N-Butyrylglycine.mol
  Mrv1652305271900222D          

 10  9  0  0  0  0            999 V2000
    1.7862   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -0.2063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862   -1.0312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5006    0.2062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    1.0312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  1  5  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
  2  6  1  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00005645c9fc4fd0>

HMDB0000808
     RDKit          3D
N-Butyrylglycine
 21 20  0  0  0  0  0  0  0  0999 V2000
   -3.7816    0.1242   -0.2523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3696    0.5443   -0.4640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3621   -0.3002    0.2501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0003    0.2392   -0.0555 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0889    1.2399   -0.8058 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1767   -0.3280    0.4621 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4507    0.2578    0.1148 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5799   -0.4766    0.7554 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3620   -1.4774    1.4963 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8910   -0.0745    0.5496 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2940   -0.0446   -1.2371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3431    0.9465    0.2367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8014   -0.7839    0.3765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1075    0.5186   -1.5508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2126    1.6007   -0.1107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5228   -0.3820    1.3314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3514   -1.3536   -0.1436 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1650   -1.1660    1.0952 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4773    1.3391    0.3981 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5293    0.1914   -1.0074 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4258   -0.6146   -0.1395 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  2 14  1  0
  2 15  1  0
  3 16  1  0
  3 17  1  0
  6 18  1  0
  7 19  1  0
  7 20  1  0
 10 21  1  0
M  END
Download

3D SDF for #<Metabolite:0x00005645c9fc4fd0>

N-Butyrylglycine.mol
  Mrv1652305271900222D          

 10  9  0  0  0  0            999 V2000
    1.7862   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -0.2063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862   -1.0312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5006    0.2062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    1.0312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  1  5  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
  2  6  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000549

> <DATABASE_NAME>
MIME

> <SMILES>
CCCC(=O)NCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H11NO3/c1-2-3-5(8)7-4-6(9)10/h2-4H2,1H3,(H,7,8)(H,9,10)

> <INCHI_KEY>
WPSSBBPLVMTKRN-UHFFFAOYSA-N

> <FORMULA>
C6H11NO3

> <MOLECULAR_WEIGHT>
145.1564

> <EXACT_MASS>
145.073893223

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
14.63825075516502

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-butanamidoacetic acid

> <ALOGPS_LOGP>
0.03

> <JCHEM_LOGP>
-0.18352444200000004

> <ALOGPS_LOGS>
-0.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.809584079020865

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.062989857092291

> <JCHEM_PKA_STRONGEST_BASIC>
-1.8713891837814174

> <JCHEM_POLAR_SURFACE_AREA>
66.4

> <JCHEM_REFRACTIVITY>
34.6751

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.76e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
butyrylglycine

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for #<Metabolite:0x00005645c9fc4fd0>

HMDB0000808
     RDKit          3D
N-Butyrylglycine
 21 20  0  0  0  0  0  0  0  0999 V2000
   -3.7816    0.1242   -0.2523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3696    0.5443   -0.4640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3621   -0.3002    0.2501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0003    0.2392   -0.0555 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0889    1.2399   -0.8058 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1767   -0.3280    0.4621 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4507    0.2578    0.1148 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5799   -0.4766    0.7554 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3620   -1.4774    1.4963 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8910   -0.0745    0.5496 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2940   -0.0446   -1.2371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3431    0.9465    0.2367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8014   -0.7839    0.3765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1075    0.5186   -1.5508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2126    1.6007   -0.1107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5228   -0.3820    1.3314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3514   -1.3536   -0.1436 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1650   -1.1660    1.0952 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4773    1.3391    0.3981 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5293    0.1914   -1.0074 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4258   -0.6146   -0.1395 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  2 14  1  0
  2 15  1  0
  3 16  1  0
  3 17  1  0
  6 18  1  0
  7 19  1  0
  7 20  1  0
 10 21  1  0
M  END
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PDB for #<Metabolite:0x00005645c9fc4fd0>

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: N-Butyrylglycine.mol                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0       3.334  -0.385   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       0.667  -0.385   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       2.001   0.385   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       3.334  -1.925   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       4.668   0.385   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -0.667   0.385   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.667   1.925   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.001  -0.385   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.334   0.385   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.668  -0.385   0.000  0.00  0.00           C+0
CONECT    1    3    4    5                                                  
CONECT    2    3    6                                                       
CONECT    3    2    1                                                       
CONECT    4    1                                                            
CONECT    5    1                                                            
CONECT    6    7    8    2                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   18    0
END
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3D PDB for #<Metabolite:0x00005645c9fc4fd0>

COMPND    HMDB0000808
HETATM    1  C1  UNL     1      -3.782   0.124  -0.252  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.370   0.544  -0.464  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.362  -0.300   0.250  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.000   0.239  -0.056  1.00  0.00           C  
HETATM    5  O1  UNL     1       0.089   1.240  -0.806  1.00  0.00           O  
HETATM    6  N1  UNL     1       1.177  -0.328   0.462  1.00  0.00           N  
HETATM    7  C5  UNL     1       2.451   0.258   0.115  1.00  0.00           C  
HETATM    8  C6  UNL     1       3.580  -0.477   0.755  1.00  0.00           C  
HETATM    9  O2  UNL     1       3.362  -1.477   1.496  1.00  0.00           O  
HETATM   10  O3  UNL     1       4.891  -0.075   0.550  1.00  0.00           O  
HETATM   11  H1  UNL     1      -4.294  -0.045  -1.237  1.00  0.00           H  
HETATM   12  H2  UNL     1      -4.343   0.946   0.237  1.00  0.00           H  
HETATM   13  H3  UNL     1      -3.801  -0.784   0.377  1.00  0.00           H  
HETATM   14  H4  UNL     1      -2.108   0.519  -1.551  1.00  0.00           H  
HETATM   15  H5  UNL     1      -2.213   1.601  -0.111  1.00  0.00           H  
HETATM   16  H6  UNL     1      -1.523  -0.382   1.331  1.00  0.00           H  
HETATM   17  H7  UNL     1      -1.351  -1.354  -0.144  1.00  0.00           H  
HETATM   18  H8  UNL     1       1.165  -1.166   1.095  1.00  0.00           H  
HETATM   19  H9  UNL     1       2.477   1.339   0.398  1.00  0.00           H  
HETATM   20  H10 UNL     1       2.529   0.191  -1.007  1.00  0.00           H  
HETATM   21  H11 UNL     1       5.426  -0.615  -0.139  1.00  0.00           H  
CONECT    1    2   11   12   13
CONECT    2    3   14   15
CONECT    3    4   16   17
CONECT    4    5    5    6
CONECT    6    7   18
CONECT    7    8   19   20
CONECT    8    9    9   10
CONECT   10   21
END
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SMILES for #<Metabolite:0x00005645c9fc4fd0>

CCCC(=O)NCC(O)=O
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INCHI for #<Metabolite:0x00005645c9fc4fd0>

InChI=1S/C6H11NO3/c1-2-3-5(8)7-4-6(9)10/h2-4H2,1H3,(H,7,8)(H,9,10)
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Synonyms
ValueSource
2-Butanamidoacetic acidChEBI
2-Butyramidoacetic acidChEBI
Butanamidoacetic acidChEBI
Butyramidoacetic acidChEBI
N-(1-Oxobutyl)glycineChEBI
N-Butyryl-glycineChEBI
2-ButanamidoacetateGenerator
2-ButyramidoacetateGenerator
ButanamidoacetateGenerator
ButyramidoacetateGenerator
N-ButanoylglycineHMDB
ButyrylglycineHMDB
N-ButyrylglycineChEBI
Molecular FormulaC6H11NO3
Average Mass145.1564
Monoisotopic Mass145.073893223
IUPAC Name2-butanamidoacetic acid
Traditional Namebutyrylglycine
CAS Registry NumberNot Available
SMILES
CCCC(=O)NCC(O)=O
InChI Identifier
InChI=1S/C6H11NO3/c1-2-3-5(8)7-4-6(9)10/h2-4H2,1H3,(H,7,8)(H,9,10)
InChI KeyWPSSBBPLVMTKRN-UHFFFAOYSA-N