MiMeDB: Showing metabocard for (3S)-3-hydroxy-L-aspartic acid (MMDBc0032932)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:27:51 UTC

Update Date

2022-08-31 21:48:44 UTC

Metabolite ID

MMDBc0032932

Metabolite Identification

Common Name

(3S)-3-hydroxy-L-aspartic acid

Description

3-Hydroxyaspartate is not found in normal proteins, it is found in cinnamycin, a 19-amino acid peptide with anti-tumor and anti-microbial activities that is produced by Streptomyces strains. (3S)-3-Hydroxy-L-aspartic acid (threo-3-hydroxyaspartate) is converted to oxaloacetate and ammonia by a 3-hydroxyaspartate dehydratase (SRY1p) in yeast. The role of this enzyme in yeast would be detoxification of naturally occuring 3-hydroxyaspartate. [PMID: 12951240 ]

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
DL-Threo-beta-hydroxyaspartic acid	ChEBI
L-Threo-3-hydroxyaspartate	Kegg
DL-Threo-b-hydroxyaspartate	Generator
DL-Threo-b-hydroxyaspartic acid	Generator
DL-Threo-beta-hydroxyaspartate	Generator
DL-Threo-β-hydroxyaspartate	Generator
DL-Threo-β-hydroxyaspartic acid	Generator
L-Threo-3-hydroxyaspartic acid	Generator
(3S)-3-Hydroxy-L-aspartate	Generator
Erythro-beta-hydroxyaspartic acid	MeSH
Threo-beta-aspartate	MeSH
L-Threo-beta-hydroxyaspartic acid	MeSH
beta-Hydroxyaspartic acid	MeSH
Threo-hydroxyaspartic acid	MeSH
3-Hydroxyaspartic acid	MeSH
3-Hydroxyaspartic acid, (erythro-L)-isomer	MeSH
DL-Threo-3-hydroxyaspartic acid	MeSH
3-Hydroxyaspartic acid, (threo-L)-isomer	MeSH
3-Hydroxyaspartic acid, (threo-DL)-isomer	MeSH
3-Hydroxyaspartic acid, (erythro-D)-isomer	MeSH
3-Hydroxyaspartic acid, (erythro-DL)-isomer	MeSH
3-Hydroxyaspartic acid, (erythro)-isomer	MeSH
Threo-tha	MeSH
L-Erythro-3-hydroxyaspartate	MeSH
threo-3-Hydroxy-L-aspartic acid	Generator

Molecular Formula

C₄H₇NO₅

Average Mass

149.1021

Monoisotopic Mass

149.032422339

IUPAC Name

(2S,3S)-2-amino-3-hydroxybutanedioic acid

Traditional Name

3-hydroxyaspartic acid

CAS Registry Number

7298-99-9

SMILES

N[C@@H]([C@H](O)C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C4H7NO5/c5-1(3(7)8)2(6)4(9)10/h1-2,6H,5H2,(H,7,8)(H,9,10)/t1-,2-/m0/s1

InChI Key

YYLQUHNPNCGKJQ-LWMBPPNESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aspartic acid and derivatives. Aspartic acid and derivatives are compounds containing an aspartic acid or a derivative thereof resulting from reaction of aspartic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Aspartic acid and derivatives

Alternative Parents

Substituents

Aspartic acid or derivatives
Alpha-amino acid
L-alpha-amino acid
Beta-hydroxy acid
Short-chain hydroxy acid
Alpha-hydroxy acid
Dicarboxylic acid or derivatives
Fatty acid
Hydroxy acid
Monosaccharide
Amino acid
Secondary alcohol
Carboxylic acid
Alcohol
Organonitrogen compound
Organooxygen compound
Primary aliphatic amine
Primary amine
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organopnictogen compound
Amine
Organic oxygen compound
Organic nitrogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

3-hydroxy-L-aspartic acid (CHEBI:10696 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	111 g/L	ALOGPS
logP	-3.4	ALOGPS
logP	-4.4	ChemAxon
logS	-0.13	ALOGPS
pKa (Strongest Acidic)	2.57	ChemAxon
pKa (Strongest Basic)	9.08	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	120.85 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	27.87 m³·mol⁻¹	ChemAxon
Polarizability	12.1 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-052f-9100000000-af8204a8797562a5e1a8	2016-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0ue9-2900000000-3532e53b3a0b32d5b387	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-9100000000-17b233107605486b5b32	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0570-9000000000-b4d1e0a4cedd017f9bb4	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udj-4900000000-b4e20ff53fc1f019de14	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udr-9700000000-446a91507f281401574d	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05fr-9000000000-e8a8b69125b8407a7211	2016-09-12	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	598.0
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-24	446.5
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (void)	2025-10-24	45.7
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-24	249.6
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (void)	2025-10-24	317.0
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (void)	2025-10-24	398.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (void)	2025-10-24	579.6
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	925.9
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-24	1089.3
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	238.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	484.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (void)	2025-10-24	254.3
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (void)	2025-10-24	28.6
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	505.1
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	764.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (void)	2025-10-24	137.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (void)	2025-10-24	405.5
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-24	767.0
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-24	645.3

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	(3S)-3-hydroxy-L-aspartic acid_TMS_1	C[Si](C)(C)O[C@H](C(=O)O)[C@H](N)C(=O)O	standard non polar	2025-10-24	1837.17
Gas Chromatography	(3S)-3-hydroxy-L-aspartic acid_TMS_2	C[Si](C)(C)OC(=O)[C@@H](O)[C@H](N)C(=O)O	standard non polar	2025-10-24	2321.53
Gas Chromatography	(3S)-3-hydroxy-L-aspartic acid_TMS_3	C[Si](C)(C)OC(=O)[C@@H](N)[C@H](O)C(=O)O	standard non polar	2025-10-24	2275.18
Gas Chromatography	(3S)-3-hydroxy-L-aspartic acid_TMS_4	C[Si](C)(C)N[C@H](C(=O)O)[C@H](O)C(=O)O	standard non polar	2025-10-24	2203.49
Gas Chromatography	(3S)-3-hydroxy-L-aspartic acid_TMS_5	C[Si](C)(C)OC(=O)[C@@H](O[Si](C)(C)C)[C@H](N)C(=O)O	standard non polar	2025-10-24	1425.91
Gas Chromatography	(3S)-3-hydroxy-L-aspartic acid_TMS_6	C[Si](C)(C)OC(=O)[C@@H](N)[C@H](O[Si](C)(C)C)C(=O)O	standard non polar	2025-10-24	1875.21
Gas Chromatography	(3S)-3-hydroxy-L-aspartic acid_TMS_7	C[Si](C)(C)N[C@H](C(=O)O)[C@H](O[Si](C)(C)C)C(=O)O	standard non polar	2025-10-24	1802.64
Gas Chromatography	(3S)-3-hydroxy-L-aspartic acid_TMS_8	C[Si](C)(C)OC(=O)[C@@H](N)[C@H](O)C(=O)O[Si](C)(C)C	standard non polar	2025-10-24	2484.39
Gas Chromatography	(3S)-3-hydroxy-L-aspartic acid_TMS_9	C[Si](C)(C)N[C@H](C(=O)O)[C@H](O)C(=O)O[Si](C)(C)C	standard non polar	2025-10-24	1779.48
Gas Chromatography	(3S)-3-hydroxy-L-aspartic acid_TMS_10	C[Si](C)(C)N[C@H](C(=O)O[Si](C)(C)C)[C@H](O)C(=O)O	standard non polar	2025-10-24	1662.8
Gas Chromatography	(3S)-3-hydroxy-L-aspartic acid_TMS_11	C[Si](C)(C)N([C@H](C(=O)O)[C@H](O)C(=O)O)[Si](C)(C)C	standard non polar	2025-10-24	1446.19
Gas Chromatography	(3S)-3-hydroxy-L-aspartic acid_TMS_12	C[Si](C)(C)OC(=O)[C@@H](N)[C@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard non polar	2025-10-24	1604.59
Gas Chromatography	(3S)-3-hydroxy-L-aspartic acid_TMS_13	C[Si](C)(C)N[C@H](C(=O)O)[C@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard non polar	2025-10-24	2142.81
Gas Chromatography	(3S)-3-hydroxy-L-aspartic acid_TMS_14	C[Si](C)(C)N[C@H](C(=O)O[Si](C)(C)C)[C@H](O[Si](C)(C)C)C(=O)O	standard non polar	2025-10-24	1560.82
Gas Chromatography	(3S)-3-hydroxy-L-aspartic acid_TMS_15	C[Si](C)(C)O[C@H](C(=O)O)[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	1727.33
Gas Chromatography	(3S)-3-hydroxy-L-aspartic acid_TMS_16	C[Si](C)(C)N[C@H](C(=O)O[Si](C)(C)C)[C@H](O)C(=O)O[Si](C)(C)C	standard non polar	2025-10-24	2013.56
Gas Chromatography	(3S)-3-hydroxy-L-aspartic acid_TMS_17	C[Si](C)(C)OC(=O)[C@@H](O)[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	1881.83
Gas Chromatography	(3S)-3-hydroxy-L-aspartic acid_TMS_18	C[Si](C)(C)OC(=O)[C@H]([C@H](O)C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	2020.85
Gas Chromatography	(3S)-3-hydroxy-L-aspartic acid_TMS_19	C[Si](C)(C)N[C@H](C(=O)O[Si](C)(C)C)[C@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard non polar	2025-10-24	2104.78
Gas Chromatography	(3S)-3-hydroxy-L-aspartic acid_TMS_20	C[Si](C)(C)OC(=O)[C@@H](O[Si](C)(C)C)[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	1880.25
Gas Chromatography	(3S)-3-hydroxy-L-aspartic acid_TMS_21	C[Si](C)(C)OC(=O)[C@H]([C@H](O[Si](C)(C)C)C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	2092.56
Gas Chromatography	(3S)-3-hydroxy-L-aspartic acid_TMS_22	C[Si](C)(C)OC(=O)[C@@H](O)[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	1866.28
Gas Chromatography	(3S)-3-hydroxy-L-aspartic acid_TMS_23	C[Si](C)(C)OC(=O)[C@@H](O[Si](C)(C)C)[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	2277.83
Gas Chromatography	(3S)-3-hydroxy-L-aspartic acid_TMS_1	C[Si](C)(C)O[C@H](C(=O)O)[C@H](N)C(=O)O	standard polar	2025-10-24	1858.61
Gas Chromatography	(3S)-3-hydroxy-L-aspartic acid_TMS_2	C[Si](C)(C)OC(=O)[C@@H](O)[C@H](N)C(=O)O	standard polar	2025-10-24	2225.59
Gas Chromatography	(3S)-3-hydroxy-L-aspartic acid_TMS_3	C[Si](C)(C)OC(=O)[C@@H](N)[C@H](O)C(=O)O	standard polar	2025-10-24	1944.43
Gas Chromatography	(3S)-3-hydroxy-L-aspartic acid_TMS_4	C[Si](C)(C)N[C@H](C(=O)O)[C@H](O)C(=O)O	standard polar	2025-10-24	1993.49
Gas Chromatography	(3S)-3-hydroxy-L-aspartic acid_TMS_5	C[Si](C)(C)OC(=O)[C@@H](O[Si](C)(C)C)[C@H](N)C(=O)O	standard polar	2025-10-24	1374.31
Gas Chromatography	(3S)-3-hydroxy-L-aspartic acid_TMS_6	C[Si](C)(C)OC(=O)[C@@H](N)[C@H](O[Si](C)(C)C)C(=O)O	standard polar	2025-10-24	2004.9
Gas Chromatography	(3S)-3-hydroxy-L-aspartic acid_TMS_7	C[Si](C)(C)N[C@H](C(=O)O)[C@H](O[Si](C)(C)C)C(=O)O	standard polar	2025-10-24	2131.63
Gas Chromatography	(3S)-3-hydroxy-L-aspartic acid_TMS_8	C[Si](C)(C)OC(=O)[C@@H](N)[C@H](O)C(=O)O[Si](C)(C)C	standard polar	2025-10-24	2366.05
Gas Chromatography	(3S)-3-hydroxy-L-aspartic acid_TMS_9	C[Si](C)(C)N[C@H](C(=O)O)[C@H](O)C(=O)O[Si](C)(C)C	standard polar	2025-10-24	1775.74
Gas Chromatography	(3S)-3-hydroxy-L-aspartic acid_TMS_10	C[Si](C)(C)N[C@H](C(=O)O[Si](C)(C)C)[C@H](O)C(=O)O	standard polar	2025-10-24	1548.06
Gas Chromatography	(3S)-3-hydroxy-L-aspartic acid_TMS_11	C[Si](C)(C)N([C@H](C(=O)O)[C@H](O)C(=O)O)[Si](C)(C)C	standard polar	2025-10-24	2280.04
Gas Chromatography	(3S)-3-hydroxy-L-aspartic acid_TMS_12	C[Si](C)(C)OC(=O)[C@@H](N)[C@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard polar	2025-10-24	2426.6
Gas Chromatography	(3S)-3-hydroxy-L-aspartic acid_TMS_13	C[Si](C)(C)N[C@H](C(=O)O)[C@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard polar	2025-10-24	1323.31
Gas Chromatography	(3S)-3-hydroxy-L-aspartic acid_TMS_14	C[Si](C)(C)N[C@H](C(=O)O[Si](C)(C)C)[C@H](O[Si](C)(C)C)C(=O)O	standard polar	2025-10-24	1993.37
Gas Chromatography	(3S)-3-hydroxy-L-aspartic acid_TMS_15	C[Si](C)(C)O[C@H](C(=O)O)[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	2602.36
Gas Chromatography	(3S)-3-hydroxy-L-aspartic acid_TMS_16	C[Si](C)(C)N[C@H](C(=O)O[Si](C)(C)C)[C@H](O)C(=O)O[Si](C)(C)C	standard polar	2025-10-24	2242.95
Gas Chromatography	(3S)-3-hydroxy-L-aspartic acid_TMS_17	C[Si](C)(C)OC(=O)[C@@H](O)[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	1996.61
Gas Chromatography	(3S)-3-hydroxy-L-aspartic acid_TMS_18	C[Si](C)(C)OC(=O)[C@H]([C@H](O)C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	2175.24
Gas Chromatography	(3S)-3-hydroxy-L-aspartic acid_TMS_19	C[Si](C)(C)N[C@H](C(=O)O[Si](C)(C)C)[C@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard polar	2025-10-24	2414.68
Gas Chromatography	(3S)-3-hydroxy-L-aspartic acid_TMS_20	C[Si](C)(C)OC(=O)[C@@H](O[Si](C)(C)C)[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	1884.92
Gas Chromatography	(3S)-3-hydroxy-L-aspartic acid_TMS_21	C[Si](C)(C)OC(=O)[C@H]([C@H](O[Si](C)(C)C)C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	1955.03
Gas Chromatography	(3S)-3-hydroxy-L-aspartic acid_TMS_22	C[Si](C)(C)OC(=O)[C@@H](O)[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	2317.72
Gas Chromatography	(3S)-3-hydroxy-L-aspartic acid_TMS_23	C[Si](C)(C)OC(=O)[C@@H](O[Si](C)(C)C)[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	1963.97

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

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
Eukaryota/Fungi	Ascomycota	2	Human feces; Human saliva	Unknown
Bacteria	Proteobacteria	1	Human feces; Human

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

C00018064

Chemspider ID

Not Available

KEGG Compound ID

C11511

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

443239

PDB ID

Not Available

ChEBI ID

10696

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

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 (3S)-3-hydroxy-L-aspartic acid (MMDBc0032932)

MOL for #<Metabolite:0x00007f9a9414bed8>

3D MOL for #<Metabolite:0x00007f9a9414bed8>

3D SDF for #<Metabolite:0x00007f9a9414bed8>

3D-SDF for #<Metabolite:0x00007f9a9414bed8>

PDB for #<Metabolite:0x00007f9a9414bed8>

3D PDB for #<Metabolite:0x00007f9a9414bed8>

SMILES for #<Metabolite:0x00007f9a9414bed8>

INCHI for #<Metabolite:0x00007f9a9414bed8>

Structure for #<Metabolite:0x00007f9a9414bed8>

3D Structure for #<Metabolite:0x00007f9a9414bed8>