MiMeDB: Showing metabocard for 7,8-Dihydro-7-hydroxy-8-S-glutathionyl-benzo[a]pyrene (MMDBc0030034)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:51:25 UTC

Update Date

2024-04-30 19:44:06 UTC

Metabolite ID

MMDBc0030034

Metabolite Identification

Common Name

7,8-Dihydro-7-hydroxy-8-S-glutathionyl-benzo[a]pyrene

Description

7,8-dihydro-7-hydroxy-8-s-glutathionyl-benzo[a]pyrene belongs to the class of Peptides. These are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another. (inferred from compound structure)

Structure

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


  Mrv0541 08131209272D          

 45 49  0  0  0  0            999 V2000
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   -0.5401    2.2736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 22 43  1  1  0  0  0
 44 23  1  0  0  0  0
 45 28  1  0  0  0  0
M  END

HMDB0060423
     RDKit          3D
7,8-Dihydro-7-hydroxy-8-S-glutathionyl-benzo[a]pyrene
 70 74  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv0541 08131209272D          

 45 49  0  0  0  0            999 V2000
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    4.3207    3.2091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7511    1.4941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9917    6.4832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2617    5.0800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4009    1.9618    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.4516    4.9241    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2110    2.1177    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1308    1.1823    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5106    3.0532    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  5  4  2  0  0  0  0
  7  6  2  0  0  0  0
 10  8  2  0  0  0  0
 11  9  1  0  0  0  0
 15  2  1  0  0  0  0
 15  4  1  0  0  0  0
 16  3  2  0  0  0  0
 16  6  1  0  0  0  0
 17  5  1  0  0  0  0
 17 12  1  0  0  0  0
 18  8  1  0  0  0  0
 19  7  1  0  0  0  0
 19 18  2  0  0  0  0
 20 12  2  0  0  0  0
 20 18  1  0  0  0  0
 21  9  1  0  0  0  0
 22 14  1  0  0  0  0
 23 10  1  0  0  0  0
 24 11  1  0  0  0  0
 25 13  1  0  0  0  0
 26 15  2  0  0  0  0
 26 16  1  0  0  0  0
 27 17  2  0  0  0  0
 27 19  1  0  0  0  0
 27 26  1  0  0  0  0
 28 20  1  0  0  0  0
 28 23  1  0  0  0  0
 29 22  1  0  0  0  0
 30 21  1  0  0  0  0
 21 31  1  1  0  0  0
 32 13  1  4  0  0  0
 32 29  2  0  0  0  0
 22 33  1  1  0  0  0
 33 24  2  0  0  0  0
 24 34  1  4  0  0  0
 35 25  2  0  0  0  0
 36 25  1  0  0  0  0
 37 28  1  0  0  0  0
 38 29  1  0  0  0  0
 39 30  2  0  0  0  0
 40 30  1  0  0  0  0
 41 14  1  0  0  0  0
 41 23  1  0  0  0  0
 21 42  1  1  0  0  0
 22 43  1  1  0  0  0
 44 23  1  0  0  0  0
 45 28  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0030034

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@](N)(CCC(O)=N[C@@]([H])(CSC1([H])C=CC2=C3C=CC4=CC=CC5=C4C3=C(C=C5)C=C2C1([H])O)C(O)=NCC(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H29N3O7S/c31-21(30(39)40)9-11-24(34)33-22(29(38)32-13-25(35)36)14-41-23-10-8-18-19-7-6-16-3-1-2-15-4-5-17(27(19)26(15)16)12-20(18)28(23)37/h1-8,10,12,21-23,28,37H,9,11,13-14,31H2,(H,32,38)(H,33,34)(H,35,36)(H,39,40)/t21-,22-,23?,28?/m0/s1

> <INCHI_KEY>
GODDWIDSELPRPA-QMIJOYDGSA-N

> <FORMULA>
C30H29N3O7S

> <MOLECULAR_WEIGHT>
575.632

> <EXACT_MASS>
575.172620987

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_AVERAGE_POLARIZABILITY>
59.37784323838076

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)-C-hydroxycarbonimidoyl]-2-({6-hydroxypentacyclo[10.6.2.0²,⁷.0⁹,¹⁹.0¹⁶,²⁰]icosa-1,3,7,9(19),10,12(20),13,15,17-nonaen-5-yl}sulfanyl)ethyl]-C-hydroxycarbonimidoyl}butanoic acid

> <ALOGPS_LOGP>
0.06

> <JCHEM_LOGP>
0.6500919563170785

> <ALOGPS_LOGS>
-5.41

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.6249847818789416

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.9988333995179182

> <JCHEM_PKA_STRONGEST_BASIC>
9.539184188617444

> <JCHEM_POLAR_SURFACE_AREA>
186.02999999999997

> <JCHEM_REFRACTIVITY>
154.76780000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.23e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-amino-4-{[(1R)-1-(carboxymethyl-C-hydroxycarbonimidoyl)-2-({6-hydroxypentacyclo[10.6.2.0²,⁷.0⁹,¹⁹.0¹⁶,²⁰]icosa-1,3,7,9(19),10,12(20),13,15,17-nonaen-5-yl}sulfanyl)ethyl]-C-hydroxycarbonimidoyl}butanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060423
     RDKit          3D
7,8-Dihydro-7-hydroxy-8-S-glutathionyl-benzo[a]pyrene
 70 74  0  0  0  0  0  0  0  0999 V2000
   -5.7971    2.9396   -0.2561 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4599    2.0267    0.5992 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.8589    0.6956    0.8055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6710   -0.2075   -0.3439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8013    0.3448   -1.3963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3658    1.3438   -2.2255 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6140    0.0356   -1.6479 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6898   -0.8687   -1.1042 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0704   -0.3944    0.2040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1902    1.1710   -0.0435 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.2262    0.8390   -1.1392 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9285    2.1019   -1.3628 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1913    2.3666   -1.1176 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0398    1.3369   -0.5628 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4715    0.1174   -0.3170 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2616   -0.8986    0.2158 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5938   -0.7011    0.4979 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3804   -1.7153    1.0290 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7033   -1.5273    1.3117 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2661   -0.3073    1.0643 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5959   -0.0407    1.3234 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1950    1.1762    1.0865 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4051    2.1654    0.5625 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0530    1.9474    0.2820 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3007    2.9614   -0.2403 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9405    2.7741   -0.5329 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3726    1.5517   -0.2861 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1610    0.5342    0.2467 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4998    0.7174    0.5351 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0625   -0.2397   -0.5648 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0775   -1.3214   -1.4702 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1152   -2.2609   -0.9319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6286   -2.9225   -2.0483 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0244   -2.8704    0.2038 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4194   -4.2217    0.4402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2796   -5.1737    0.4086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0982   -4.8127    0.1954 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5326   -6.5169    0.6236 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5827    2.6590    1.9635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1136    3.7985    2.1375 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1937    2.0153    3.0095 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1237    3.5865    0.2315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4242    3.5618   -0.8094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5345    1.9673    0.2393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8800    0.8088    1.3703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5064    0.1735    1.5818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6312   -0.5996   -0.7675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1561   -1.1514    0.0060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9443    1.6866   -3.0539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8113   -0.9192   -1.8275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3150   -1.1526    0.4918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8003   -0.3325    1.0212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2319    0.5324   -2.1195 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3232    2.9165   -1.7843 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5515    3.3575   -1.3436 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8531   -1.8829    0.4272 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9180   -2.6711    1.2170 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2966   -2.3173    1.7204 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1999   -0.8291    1.7341 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2470    1.3424    1.3064 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8698    3.1208    0.3749 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7205    3.9379   -0.4463 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3734    3.5719   -0.9375 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6589   -0.6806    0.3894 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4901   -1.0059   -2.2970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0877   -3.6511   -2.4969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8243   -4.2706    1.4899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2414   -4.5713   -0.2133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0243   -7.0431   -0.0677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1853    1.8959    3.0820 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  1  0
  5  6  1  0
  5  7  2  3
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 15 30  1  0
 30 31  1  0
  8 32  1  0
 32 33  1  0
 32 34  2  3
 34 35  1  0
 35 36  1  0
 36 37  2  0
 36 38  1  0
  2 39  1  0
 39 40  2  0
 39 41  1  0
 30 11  1  0
 27 14  1  0
 28 17  1  0
 29 20  1  0
 29 24  1  0
  1 42  1  0
  1 43  1  0
  2 44  1  6
  3 45  1  0
  3 46  1  0
  4 47  1  0
  4 48  1  0
  6 49  1  0
  8 50  1  6
  9 51  1  0
  9 52  1  0
 11 53  1  0
 12 54  1  0
 13 55  1  0
 16 56  1  0
 18 57  1  0
 19 58  1  0
 21 59  1  0
 22 60  1  0
 23 61  1  0
 25 62  1  0
 26 63  1  0
 30 64  1  0
 31 65  1  0
 33 66  1  0
 35 67  1  0
 35 68  1  0
 38 69  1  0
 41 70  1  0
M  END

HEADER    PROTEIN                                 13-AUG-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-AUG-12         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   31  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   32  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   33  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   34  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   41  S   UNK     0       0.000   0.000   0.000  0.00  0.00           S+0
HETATM   42  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   43  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   45  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1    2    3                                                       
CONECT    2    1   15                                                       
CONECT    3    1   16                                                       
CONECT    4    5   15                                                       
CONECT    5    4   17                                                       
CONECT    6    7   16                                                       
CONECT    7    6   19                                                       
CONECT    8   10   18                                                       
CONECT    9   11   21                                                       
CONECT   10    8   23                                                       
CONECT   11    9   24                                                       
CONECT   12   17   20                                                       
CONECT   13   25   32                                                       
CONECT   14   22   41                                                       
CONECT   15    2    4   26                                                  
CONECT   16    3    6   26                                                  
CONECT   17    5   12   27                                                  
CONECT   18    8   19   20                                                  
CONECT   19    7   18   27                                                  
CONECT   20   12   18   28                                                  
CONECT   21    9   30   31   42                                             
CONECT   22   14   29   33   43                                             
CONECT   23   10   28   41   44                                             
CONECT   24   11   33   34                                                  
CONECT   25   13   35   36                                                  
CONECT   26   15   16   27                                                  
CONECT   27   17   19   26                                                  
CONECT   28   20   23   37   45                                             
CONECT   29   22   32   38                                                  
CONECT   30   21   39   40                                                  
CONECT   31   21                                                            
CONECT   32   13   29                                                       
CONECT   33   22   24                                                       
CONECT   34   24                                                            
CONECT   35   25                                                            
CONECT   36   25                                                            
CONECT   37   28                                                            
CONECT   38   29                                                            
CONECT   39   30                                                            
CONECT   40   30                                                            
CONECT   41   14   23                                                       
CONECT   42   21                                                            
CONECT   43   22                                                            
CONECT   44   23                                                            
CONECT   45   28                                                            
MASTER        0    0    0    0    0    0    0    0   45    0   98    0
END

COMPND    HMDB0060423
HETATM    1  N1  UNL     1      -5.797   2.940  -0.256  1.00  0.00           N  
HETATM    2  C1  UNL     1      -6.460   2.027   0.599  1.00  0.00           C  
HETATM    3  C2  UNL     1      -5.859   0.696   0.805  1.00  0.00           C  
HETATM    4  C3  UNL     1      -5.671  -0.207  -0.344  1.00  0.00           C  
HETATM    5  C4  UNL     1      -4.801   0.345  -1.396  1.00  0.00           C  
HETATM    6  O1  UNL     1      -5.366   1.344  -2.225  1.00  0.00           O  
HETATM    7  N2  UNL     1      -3.614   0.036  -1.648  1.00  0.00           N  
HETATM    8  C5  UNL     1      -2.690  -0.869  -1.104  1.00  0.00           C  
HETATM    9  C6  UNL     1      -2.070  -0.394   0.204  1.00  0.00           C  
HETATM   10  S1  UNL     1      -1.190   1.171  -0.043  1.00  0.00           S  
HETATM   11  C7  UNL     1       0.226   0.839  -1.139  1.00  0.00           C  
HETATM   12  C8  UNL     1       0.929   2.102  -1.363  1.00  0.00           C  
HETATM   13  C9  UNL     1       2.191   2.367  -1.118  1.00  0.00           C  
HETATM   14  C10 UNL     1       3.040   1.337  -0.563  1.00  0.00           C  
HETATM   15  C11 UNL     1       2.471   0.117  -0.317  1.00  0.00           C  
HETATM   16  C12 UNL     1       3.262  -0.899   0.216  1.00  0.00           C  
HETATM   17  C13 UNL     1       4.594  -0.701   0.498  1.00  0.00           C  
HETATM   18  C14 UNL     1       5.380  -1.715   1.029  1.00  0.00           C  
HETATM   19  C15 UNL     1       6.703  -1.527   1.312  1.00  0.00           C  
HETATM   20  C16 UNL     1       7.266  -0.307   1.064  1.00  0.00           C  
HETATM   21  C17 UNL     1       8.596  -0.041   1.323  1.00  0.00           C  
HETATM   22  C18 UNL     1       9.195   1.176   1.086  1.00  0.00           C  
HETATM   23  C19 UNL     1       8.405   2.165   0.563  1.00  0.00           C  
HETATM   24  C20 UNL     1       7.053   1.947   0.282  1.00  0.00           C  
HETATM   25  C21 UNL     1       6.301   2.961  -0.240  1.00  0.00           C  
HETATM   26  C22 UNL     1       4.941   2.774  -0.533  1.00  0.00           C  
HETATM   27  C23 UNL     1       4.373   1.552  -0.286  1.00  0.00           C  
HETATM   28  C24 UNL     1       5.161   0.534   0.247  1.00  0.00           C  
HETATM   29  C25 UNL     1       6.500   0.717   0.535  1.00  0.00           C  
HETATM   30  C26 UNL     1       1.062  -0.240  -0.565  1.00  0.00           C  
HETATM   31  O2  UNL     1       1.078  -1.321  -1.470  1.00  0.00           O  
HETATM   32  C27 UNL     1      -3.115  -2.261  -0.932  1.00  0.00           C  
HETATM   33  O3  UNL     1      -3.629  -2.922  -2.048  1.00  0.00           O  
HETATM   34  N3  UNL     1      -3.024  -2.870   0.204  1.00  0.00           N  
HETATM   35  C28 UNL     1      -3.419  -4.222   0.440  1.00  0.00           C  
HETATM   36  C29 UNL     1      -2.280  -5.174   0.409  1.00  0.00           C  
HETATM   37  O4  UNL     1      -1.098  -4.813   0.195  1.00  0.00           O  
HETATM   38  O5  UNL     1      -2.533  -6.517   0.624  1.00  0.00           O  
HETATM   39  C30 UNL     1      -6.583   2.659   1.964  1.00  0.00           C  
HETATM   40  O6  UNL     1      -6.114   3.798   2.137  1.00  0.00           O  
HETATM   41  O7  UNL     1      -7.194   2.015   3.009  1.00  0.00           O  
HETATM   42  H1  UNL     1      -5.124   3.586   0.232  1.00  0.00           H  
HETATM   43  H2  UNL     1      -6.424   3.562  -0.809  1.00  0.00           H  
HETATM   44  H3  UNL     1      -7.534   1.967   0.239  1.00  0.00           H  
HETATM   45  H4  UNL     1      -4.880   0.809   1.370  1.00  0.00           H  
HETATM   46  H5  UNL     1      -6.506   0.174   1.582  1.00  0.00           H  
HETATM   47  H6  UNL     1      -6.631  -0.600  -0.767  1.00  0.00           H  
HETATM   48  H7  UNL     1      -5.156  -1.151   0.006  1.00  0.00           H  
HETATM   49  H8  UNL     1      -4.944   1.687  -3.054  1.00  0.00           H  
HETATM   50  H9  UNL     1      -1.811  -0.919  -1.827  1.00  0.00           H  
HETATM   51  H10 UNL     1      -1.315  -1.153   0.492  1.00  0.00           H  
HETATM   52  H11 UNL     1      -2.800  -0.333   1.021  1.00  0.00           H  
HETATM   53  H12 UNL     1      -0.232   0.532  -2.119  1.00  0.00           H  
HETATM   54  H13 UNL     1       0.323   2.916  -1.784  1.00  0.00           H  
HETATM   55  H14 UNL     1       2.551   3.358  -1.344  1.00  0.00           H  
HETATM   56  H15 UNL     1       2.853  -1.883   0.427  1.00  0.00           H  
HETATM   57  H16 UNL     1       4.918  -2.671   1.217  1.00  0.00           H  
HETATM   58  H17 UNL     1       7.297  -2.317   1.720  1.00  0.00           H  
HETATM   59  H18 UNL     1       9.200  -0.829   1.734  1.00  0.00           H  
HETATM   60  H19 UNL     1      10.247   1.342   1.306  1.00  0.00           H  
HETATM   61  H20 UNL     1       8.870   3.121   0.375  1.00  0.00           H  
HETATM   62  H21 UNL     1       6.721   3.938  -0.446  1.00  0.00           H  
HETATM   63  H22 UNL     1       4.373   3.572  -0.938  1.00  0.00           H  
HETATM   64  H23 UNL     1       0.659  -0.681   0.389  1.00  0.00           H  
HETATM   65  H24 UNL     1       1.490  -1.006  -2.297  1.00  0.00           H  
HETATM   66  H25 UNL     1      -3.088  -3.651  -2.497  1.00  0.00           H  
HETATM   67  H26 UNL     1      -3.824  -4.271   1.490  1.00  0.00           H  
HETATM   68  H27 UNL     1      -4.241  -4.571  -0.213  1.00  0.00           H  
HETATM   69  H28 UNL     1      -3.024  -7.043  -0.068  1.00  0.00           H  
HETATM   70  H29 UNL     1      -8.185   1.896   3.082  1.00  0.00           H  
CONECT    1    2   42   43
CONECT    2    3   39   44
CONECT    3    4   45   46
CONECT    4    5   47   48
CONECT    5    6    7    7
CONECT    6   49
CONECT    7    8
CONECT    8    9   32   50
CONECT    9   10   51   52
CONECT   10   11
CONECT   11   12   30   53
CONECT   12   13   13   54
CONECT   13   14   55
CONECT   14   15   15   27
CONECT   15   16   30
CONECT   16   17   17   56
CONECT   17   18   28
CONECT   18   19   19   57
CONECT   19   20   58
CONECT   20   21   21   29
CONECT   21   22   59
CONECT   22   23   23   60
CONECT   23   24   61
CONECT   24   25   25   29
CONECT   25   26   62
CONECT   26   27   27   63
CONECT   27   28
CONECT   28   29   29
CONECT   30   31   64
CONECT   31   65
CONECT   32   33   34   34
CONECT   33   66
CONECT   34   35
CONECT   35   36   67   68
CONECT   36   37   37   38
CONECT   38   69
CONECT   39   40   40   41
CONECT   41   70
END

HMDB0060423
     RDKit          3D
7,8-Dihydro-7-hydroxy-8-S-glutathionyl-benzo[a]pyrene
 70 74  0  0  0  0  0  0  0  0999 V2000
   -5.7971    2.9396   -0.2561 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4599    2.0267    0.5992 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.8589    0.6956    0.8055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6710   -0.2075   -0.3439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8013    0.3448   -1.3963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3658    1.3438   -2.2255 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6140    0.0356   -1.6479 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6898   -0.8687   -1.1042 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0704   -0.3944    0.2040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1902    1.1710   -0.0435 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.2262    0.8390   -1.1392 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9285    2.1019   -1.3628 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1913    2.3666   -1.1176 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0398    1.3369   -0.5628 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4715    0.1174   -0.3170 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2616   -0.8986    0.2158 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5938   -0.7011    0.4979 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3804   -1.7153    1.0290 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7033   -1.5273    1.3117 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2661   -0.3073    1.0643 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5959   -0.0407    1.3234 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1950    1.1762    1.0865 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4051    2.1654    0.5625 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0530    1.9474    0.2820 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3007    2.9614   -0.2403 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9405    2.7741   -0.5329 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3726    1.5517   -0.2861 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1610    0.5342    0.2467 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4998    0.7174    0.5351 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0625   -0.2397   -0.5648 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0775   -1.3214   -1.4702 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1152   -2.2609   -0.9319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6286   -2.9225   -2.0483 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0244   -2.8704    0.2038 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4194   -4.2217    0.4402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2796   -5.1737    0.4086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0982   -4.8127    0.1954 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5326   -6.5169    0.6236 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5827    2.6590    1.9635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1136    3.7985    2.1375 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1937    2.0153    3.0095 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1237    3.5865    0.2315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4242    3.5618   -0.8094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5345    1.9673    0.2393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8800    0.8088    1.3703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5064    0.1735    1.5818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6312   -0.5996   -0.7675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1561   -1.1514    0.0060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9443    1.6866   -3.0539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8113   -0.9192   -1.8275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3150   -1.1526    0.4918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8003   -0.3325    1.0212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2319    0.5324   -2.1195 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3232    2.9165   -1.7843 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5515    3.3575   -1.3436 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8531   -1.8829    0.4272 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9180   -2.6711    1.2170 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2966   -2.3173    1.7204 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1999   -0.8291    1.7341 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2470    1.3424    1.3064 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8698    3.1208    0.3749 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7205    3.9379   -0.4463 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3734    3.5719   -0.9375 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6589   -0.6806    0.3894 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4901   -1.0059   -2.2970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0877   -3.6511   -2.4969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8243   -4.2706    1.4899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2414   -4.5713   -0.2133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0243   -7.0431   -0.0677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1853    1.8959    3.0820 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  1  0
  5  6  1  0
  5  7  2  3
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 15 30  1  0
 30 31  1  0
  8 32  1  0
 32 33  1  0
 32 34  2  3
 34 35  1  0
 35 36  1  0
 36 37  2  0
 36 38  1  0
  2 39  1  0
 39 40  2  0
 39 41  1  0
 30 11  1  0
 27 14  1  0
 28 17  1  0
 29 20  1  0
 29 24  1  0
  1 42  1  0
  1 43  1  0
  2 44  1  6
  3 45  1  0
  3 46  1  0
  4 47  1  0
  4 48  1  0
  6 49  1  0
  8 50  1  6
  9 51  1  0
  9 52  1  0
 11 53  1  0
 12 54  1  0
 13 55  1  0
 16 56  1  0
 18 57  1  0
 19 58  1  0
 21 59  1  0
 22 60  1  0
 23 61  1  0
 25 62  1  0
 26 63  1  0
 30 64  1  0
 31 65  1  0
 33 66  1  0
 35 67  1  0
 35 68  1  0
 38 69  1  0
 41 70  1  0
M  END

Synonyms

Not Available

Molecular Formula

C₃₀H₂₉N₃O₇S

Average Mass

575.632

Monoisotopic Mass

575.172620987

IUPAC Name

(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)-C-hydroxycarbonimidoyl]-2-({6-hydroxypentacyclo[10.6.2.0²,⁷.0⁹,¹⁹.0¹⁶,²⁰]icosa-1,3,7,9(19),10,12(20),13,15,17-nonaen-5-yl}sulfanyl)ethyl]-C-hydroxycarbonimidoyl}butanoic acid

Traditional Name

(2S)-2-amino-4-{[(1R)-1-(carboxymethyl-C-hydroxycarbonimidoyl)-2-({6-hydroxypentacyclo[10.6.2.0²,⁷.0⁹,¹⁹.0¹⁶,²⁰]icosa-1,3,7,9(19),10,12(20),13,15,17-nonaen-5-yl}sulfanyl)ethyl]-C-hydroxycarbonimidoyl}butanoic acid

CAS Registry Number

Not Available

SMILES

[H][C@](N)(CCC(O)=N[C@@]([H])(CSC1([H])C=CC2=C3C=CC4=CC=CC5=C4C3=C(C=C5)C=C2C1([H])O)C(O)=NCC(O)=O)C(O)=O

InChI Identifier

InChI=1S/C30H29N3O7S/c31-21(30(39)40)9-11-24(34)33-22(29(38)32-13-25(35)36)14-41-23-10-8-18-19-7-6-16-3-1-2-15-4-5-17(27(19)26(15)16)12-20(18)28(23)37/h1-8,10,12,21-23,28,37H,9,11,13-14,31H2,(H,32,38)(H,33,34)(H,35,36)(H,39,40)/t21-,22-,23?,28?/m0/s1

InChI Key

GODDWIDSELPRPA-QMIJOYDGSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Oligopeptides

Alternative Parents

Substituents

Alpha-oligopeptide
Gamma-glutamyl alpha peptide
Pyrene
Phenanthrol
Glutamine or derivatives
Phenanthrene
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
Alpha-amino acid amide
Cysteine or derivatives
Naphthalene
Alpha-amino acid or derivatives
N-substituted-alpha-amino acid
Alpha-amino acid
L-alpha-amino acid
Fatty acyl
Benzenoid
Dicarboxylic acid or derivatives
Fatty amide
N-acyl-amine
Carboxamide group
Secondary carboxylic acid amide
Secondary alcohol
Amino acid
Amino acid or derivatives
Dialkylthioether
Carboxylic acid
Sulfenyl compound
Thioether
Primary amine
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Amine
Organic oxide
Primary aliphatic amine
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

glutathione derivative (CHEBI:34479 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.0022 g/L	ALOGPS
logP	0.06	ALOGPS
logP	0.65	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	2	ChemAxon
pKa (Strongest Basic)	9.54	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	186.03 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	154.77 m³·mol⁻¹	ChemAxon
Polarizability	59.38 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Not Available

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192428	Glutathione S-transferase Mu 2	Enzyme	P28161	Homo sapiens
MMDBp0192431	Glutathione S-transferase Mu 1	Enzyme	P09488	Homo sapiens
MMDBp0192433	Glutathione S-transferase kappa 1	Enzyme	Q9Y2Q3	Homo sapiens
MMDBp0192434	Microsomal glutathione S-transferase 3	Enzyme	O14880	Homo sapiens
MMDBp0192435	Glutathione S-transferase Mu 3	Enzyme	P21266	Homo sapiens
MMDBp0192436	Glutathione S-transferase A1	Enzyme	P08263	Homo sapiens
MMDBp0192438	Microsomal glutathione S-transferase 1	Enzyme	P10620	Homo sapiens
MMDBp0192439	Glutathione S-transferase Mu 4	Enzyme	Q03013	Homo sapiens
MMDBp0192440	Glutathione S-transferase Mu 5	Enzyme	P46439	Homo sapiens
MMDBp0192441	Microsomal glutathione S-transferase 2	Enzyme	Q99735	Homo sapiens
MMDBp0192442	Glutathione S-transferase omega-1	Enzyme	P78417	Homo sapiens
MMDBp0192443	Glutathione S-transferase A5	Enzyme	Q7RTV2	Homo sapiens
MMDBp0192444	Glutathione S-transferase A2	Enzyme	P09210	Homo sapiens
MMDBp0192446	Glutathione S-transferase A3	Enzyme	Q16772	Homo sapiens
MMDBp0192447	Glutathione S-transferase A4	Enzyme	O15217	Homo sapiens
MMDBp0192451	Glutathione S-transferase omega-2	Enzyme	Q9H4Y5	Homo sapiens
MMDBp0192452	Glutathione S-transferase theta-1	Unknown	P30711	Homo sapiens
MMDBp0192454	Glutathione S-transferase P	Enzyme	P09211	Homo sapiens
MMDBp0196825	Glutathione S-transferase theta-2B	Unknown	P0CG30

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

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
Bacteria/Eubacteria	Proteobacteria	1	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool	Unknown

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 Feces	Detected but not Quantified									HMDB

External Links

HMDB ID

HMDB0060423

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

10128364

KEGG Compound ID

C14856

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11954069

PDB ID

Not Available

ChEBI ID

34479

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]

Showing metabocard for 7,8-Dihydro-7-hydroxy-8-S-glutathionyl-benzo[a]pyrene (MMDBc0030034)

MOL for #<Metabolite:0x00007f9234017430>

3D MOL for #<Metabolite:0x00007f9234017430>

3D SDF for #<Metabolite:0x00007f9234017430>

3D-SDF for #<Metabolite:0x00007f9234017430>

PDB for #<Metabolite:0x00007f9234017430>

3D PDB for #<Metabolite:0x00007f9234017430>

SMILES for #<Metabolite:0x00007f9234017430>

INCHI for #<Metabolite:0x00007f9234017430>

Structure for #<Metabolite:0x00007f9234017430>

3D Structure for #<Metabolite:0x00007f9234017430>