MiMeDB: Showing metabocard for Tetrahydromonapterin (MMDBc0031637)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 01:42:24 UTC

Update Date

2022-08-31 18:22:44 UTC

Metabolite ID

MMDBc0031637

Metabolite Identification

Common Name

Tetrahydromonapterin

Description

Tetrahydromonapterin is a member of the chemical class known as Biopterins and Derivatives. These are coenzymes containing a 2-amino-pteridine-4-one derivative. Tetrahydromonapterin is a major pterin in Escherichia coli and is hypothesized to be the cofactor for phenylalanine hydroxylase (PhhA) in Pseudomonas aeruginosa, but neither its biosynthetic origin nor its cofactor role has been clearly demonstrated. Collectively, these data establish that tetrahydromonapterin formation requires both FolX and FolM, that tetrahydromonapterin is the physiological cofactor for PhhA, and that tetrahydromonapterin can outrank folate as an end product of pterin biosynthesis. (PMID 19897652 )

Structure

MOL SDF PDB SMILES InChI

45479608
  Mrv0541 07251214082D          

 33 34  0  0  1  0            999 V2000
    4.2365   -1.3797    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    0.6829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930   -0.1422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1079   -1.4082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6655   -0.5547    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6655    1.0954    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1174    1.1240    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8650   -0.1593    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5779    1.1153    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509   -0.1422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -0.5547    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9509    0.6829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -0.1422    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3799   -0.1422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3799    0.6829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -0.5547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1174   -0.5833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8650    0.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509   -0.6537    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6795   -0.8104    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7760    1.1635    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4473    0.5940    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9650    0.1136    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6655   -1.0662    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6655    1.6069    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4787   -0.9465    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1363   -0.9465    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.6354    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1116    1.6354    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    0.9386    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.3979    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0218    0.8612    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5759    1.6268    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 11  1  1  6  0  0  0
  1 28  1  0  0  0  0
 13  2  1  6  0  0  0
  2 30  1  0  0  0  0
  3 16  1  0  0  0  0
  3 31  1  0  0  0  0
  4 17  2  0  0  0  0
  5 10  1  0  0  0  0
  5 14  1  0  0  0  0
  5 24  1  0  0  0  0
  6 12  1  0  0  0  0
  6 15  1  0  0  0  0
  6 25  1  0  0  0  0
  7 15  1  0  0  0  0
  7 18  1  0  0  0  0
  7 29  1  0  0  0  0
  8 17  1  0  0  0  0
  8 18  2  0  0  0  0
  9 18  1  0  0  0  0
  9 32  1  0  0  0  0
  9 33  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 10 19  1  0  0  0  0
 11 13  1  0  0  0  0
 11 20  1  0  0  0  0
 12 21  1  0  0  0  0
 12 22  1  0  0  0  0
 13 16  1  0  0  0  0
 13 23  1  0  0  0  0
 14 15  2  0  0  0  0
 14 17  1  0  0  0  0
 16 26  1  0  0  0  0
 16 27  1  0  0  0  0
M  END

45479608
  Mrv0541 07251214082D          

 33 34  0  0  1  0            999 V2000
    4.2365   -1.3797    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    0.6829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930   -0.1422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1079   -1.4082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6655   -0.5547    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6655    1.0954    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1174    1.1240    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8650   -0.1593    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5779    1.1153    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509   -0.1422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -0.5547    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9509    0.6829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -0.1422    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3799   -0.1422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3799    0.6829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -0.5547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1174   -0.5833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8650    0.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509   -0.6537    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6795   -0.8104    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7760    1.1635    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4473    0.5940    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9650    0.1136    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6655   -1.0662    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6655    1.6069    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4787   -0.9465    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1363   -0.9465    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.6354    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1116    1.6354    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    0.9386    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.3979    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0218    0.8612    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5759    1.6268    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 11  1  1  6  0  0  0
  1 28  1  0  0  0  0
 13  2  1  6  0  0  0
  2 30  1  0  0  0  0
  3 16  1  0  0  0  0
  3 31  1  0  0  0  0
  4 17  2  0  0  0  0
  5 10  1  0  0  0  0
  5 14  1  0  0  0  0
  5 24  1  0  0  0  0
  6 12  1  0  0  0  0
  6 15  1  0  0  0  0
  6 25  1  0  0  0  0
  7 15  1  0  0  0  0
  7 18  1  0  0  0  0
  7 29  1  0  0  0  0
  8 17  1  0  0  0  0
  8 18  2  0  0  0  0
  9 18  1  0  0  0  0
  9 32  1  0  0  0  0
  9 33  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 10 19  1  0  0  0  0
 11 13  1  0  0  0  0
 11 20  1  0  0  0  0
 12 21  1  0  0  0  0
 12 22  1  0  0  0  0
 13 16  1  0  0  0  0
 13 23  1  0  0  0  0
 14 15  2  0  0  0  0
 14 17  1  0  0  0  0
 16 26  1  0  0  0  0
 16 27  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0031637

> <DATABASE_NAME>
MIME

> <SMILES>
[H]OC([H])([H])[C@]([H])(O[H])[C@@]([H])(O[H])C1([H])N([H])C2=C(N([H])C(=NC2=O)N([H])[H])N([H])C1([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C9H15N5O4/c10-9-13-7-5(8(18)14-9)12-3(1-11-7)6(17)4(16)2-15/h3-4,6,12,15-17H,1-2H2,(H4,10,11,13,14,18)/t3?,4-,6-/m0/s1

> <INCHI_KEY>
XHIXPVCTDRNTTC-YQVKZWHSSA-N

> <FORMULA>
C9H15N5O4

> <MOLECULAR_WEIGHT>
257.2465

> <EXACT_MASS>
257.112403993

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
24.58720524801251

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-6-[(1S,2S)-1,2,3-trihydroxypropyl]-1,4,5,6,7,8-hexahydropteridin-4-one

> <ALOGPS_LOGP>
-2.19

> <JCHEM_LOGP>
-3.709039727333333

> <ALOGPS_LOGS>
-1.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.136413073858211

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.009066642719565

> <JCHEM_PKA_STRONGEST_BASIC>
3.577781487756159

> <JCHEM_POLAR_SURFACE_AREA>
152.23

> <JCHEM_REFRACTIVITY>
69.97710000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.68e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-amino-6-[(1S,2S)-1,2,3-trihydroxypropyl]-5,6,7,8-tetrahydro-1H-pteridin-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-JUL-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 45479608                                          
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-JUL-12         0                                  
HETATM    1  O   UNK     0       7.908  -2.575   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       6.574   1.275   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       3.907  -0.265   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      13.268  -2.629   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0      10.576  -1.035   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0      10.576   2.045   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0      13.286   2.098   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0      14.681  -0.297   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0      16.012   2.082   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       9.242  -0.265   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.908  -1.035   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.242   1.275   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.574  -0.265   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.909  -0.265   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.909   1.275   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.241  -1.035   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.286  -1.089   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.681   1.307   0.000  0.00  0.00           C+0
HETATM   19  H   UNK     0       9.242  -1.220   0.000  0.00  0.00           H+0
HETATM   20  H   UNK     0       8.735  -1.513   0.000  0.00  0.00           H+0
HETATM   21  H   UNK     0       8.915   2.172   0.000  0.00  0.00           H+0
HETATM   22  H   UNK     0       8.302   1.109   0.000  0.00  0.00           H+0
HETATM   23  H   UNK     0       7.401   0.212   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0      10.576  -1.990   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0      10.576   3.000   0.000  0.00  0.00           H+0
HETATM   26  H   UNK     0       4.627  -1.767   0.000  0.00  0.00           H+0
HETATM   27  H   UNK     0       5.854  -1.767   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0       7.081  -3.053   0.000  0.00  0.00           H+0
HETATM   29  H   UNK     0      13.275   3.053   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0       5.747   1.752   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0       3.080  -0.743   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0      16.841   1.608   0.000  0.00  0.00           H+0
HETATM   33  H   UNK     0      16.008   3.037   0.000  0.00  0.00           H+0
CONECT    1   11   28                                                       
CONECT    2   13   30                                                       
CONECT    3   16   31                                                       
CONECT    4   17                                                            
CONECT    5   10   14   24                                                  
CONECT    6   12   15   25                                                  
CONECT    7   15   18   29                                                  
CONECT    8   17   18                                                       
CONECT    9   18   32   33                                                  
CONECT   10    5   11   12   19                                             
CONECT   11    1   10   13   20                                             
CONECT   12    6   10   21   22                                             
CONECT   13    2   11   16   23                                             
CONECT   14    5   15   17                                                  
CONECT   15    6    7   14                                                  
CONECT   16    3   13   26   27                                             
CONECT   17    4    8   14                                                  
CONECT   18    7    8    9                                                  
CONECT   19   10                                                            
CONECT   20   11                                                            
CONECT   21   12                                                            
CONECT   22   12                                                            
CONECT   23   13                                                            
CONECT   24    5                                                            
CONECT   25    6                                                            
CONECT   26   16                                                            
CONECT   27   16                                                            
CONECT   28    1                                                            
CONECT   29    7                                                            
CONECT   30    2                                                            
CONECT   31    3                                                            
CONECT   32    9                                                            
CONECT   33    9                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   68    0
END

Synonyms

Value	Source
5,6,7,8-Tetrahydromonapterin	ChEBI
H4-MPT	ChEBI

Molecular Formula

C₉H₁₅N₅O₄

Average Mass

257.2465

Monoisotopic Mass

257.112403993

IUPAC Name

2-amino-6-[(1S,2S)-1,2,3-trihydroxypropyl]-1,4,5,6,7,8-hexahydropteridin-4-one

Traditional Name

2-amino-6-[(1S,2S)-1,2,3-trihydroxypropyl]-5,6,7,8-tetrahydro-1H-pteridin-4-one

CAS Registry Number

Not Available

SMILES

[H]OC([H])([H])[C@]([H])(O[H])[C@@]([H])(O[H])C1([H])N([H])C2=C(N([H])C(=NC2=O)N([H])[H])N([H])C1([H])[H]

InChI Identifier

InChI=1S/C9H15N5O4/c10-9-13-7-5(8(18)14-9)12-3(1-11-7)6(17)4(16)2-15/h3-4,6,12,15-17H,1-2H2,(H4,10,11,13,14,18)/t3?,4-,6-/m0/s1

InChI Key

XHIXPVCTDRNTTC-YQVKZWHSSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as biopterins and derivatives. These are coenzymes containing a 2-amino-pteridine-4-one derivative. They are mainly synthesized in several parts of the body, including the pineal gland.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pteridines and derivatives

Sub Class

Pterins and derivatives

Direct Parent

Biopterins and derivatives

Alternative Parents

Substituents

Biopterin
Aminopyrimidine
Pyrimidone
Secondary aliphatic/aromatic amine
Pyrimidine
Heteroaromatic compound
Vinylogous amide
1,3-aminoalcohol
Secondary alcohol
1,2-aminoalcohol
Azacycle
Secondary amine
Polyol
Hydrocarbon derivative
Primary amine
Primary alcohol
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Amine
Alcohol
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tetrahydropterin (CHEBI:71177 )
neopterins (CHEBI:71177 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	4.68 g/L	ALOGPS
logP	-2.2	ALOGPS
logP	-3.7	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	10.01	ChemAxon
pKa (Strongest Basic)	3.58	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	152.23 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	69.98 m³·mol⁻¹	ChemAxon
Polarizability	24.59 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Not Available

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

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

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0019232	Dihydromethysticin	Tetrahydromonapterin	Dihydromonapterin reductase	Reduction	PathBank	31602464

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	17	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool	Unknown
Bacteria	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

External Links

HMDB ID

Not Available

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

CPD0-2101

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

45479608

PDB ID

Not Available

ChEBI ID

71177

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Wishart DS, Li C, Marcu A, Badran H, Pon A, Budinski Z, Patron J, Lipton D, Cao X, Oler E, Li K, Paccoud M, Hong C, Guo AC, Chan C, Wei W, Ramirez-Gaona M: PathBank: a comprehensive pathway database for model organisms. Nucleic Acids Res. 2020 Jan 8;48(D1):D470-D478. doi: 10.1093/nar/gkz861. [PubMed:31602464 ]
Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for Tetrahydromonapterin (MMDBc0031637)

MOL for #<Metabolite:0x00007f922ab86b18>

3D MOL for #<Metabolite:0x00007f922ab86b18>

3D SDF for #<Metabolite:0x00007f922ab86b18>

3D-SDF for #<Metabolite:0x00007f922ab86b18>

PDB for #<Metabolite:0x00007f922ab86b18>

3D PDB for #<Metabolite:0x00007f922ab86b18>

SMILES for #<Metabolite:0x00007f922ab86b18>

INCHI for #<Metabolite:0x00007f922ab86b18>

Structure for #<Metabolite:0x00007f922ab86b18>

3D Structure for #<Metabolite:0x00007f922ab86b18>