MiMeDB: Showing metabocard for Indolelactic acid (MMDBc0000135)

Not Available

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-10-27 23:37:09 UTC

Update Date

2024-10-13 12:57:20 UTC

Metabolite ID

MMDBc0000135

Metabolite Identification

Common Name

Indolelactic acid

Description

Indolelactic acid (CAS: 1821-52-9) is a tryptophan metabolite found in human plasma, serum, and urine. Tryptophan is metabolized by two major pathways in humans, either through kynurenine or via a series of indoles, and some of its metabolites are known to be biologically active. Indolelactic acid is present in various amounts, significantly higher in umbilical fetal plasma than in maternal plasma in the protein-bound form (PMID 2361979 , 1400722 , 3597614 , 11060358 , 1400722 ). Indolelactic acid is also a microbial metabolite; urinary indole-3-lactate is produced by Clostridium sporogenes (PMID: 29168502 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Indolelactate	Generator
3-(indol-3-yl) LACTic acid	HMDB
(2S)-2-Hydroxy-3-(1H-indol-3-yl)propanoic acid	HMDB
(2S)-2-Hydroxy-3-(1H-indol-3-yl)propionic acid	HMDB
(2S)-2-Hydroxy-3-indoylpropanoic acid	HMDB
(2S)-2-Hydroxy-3-indoylpropionic acid	HMDB
(S)-2-Hydroxy-3-(1H-indol-3-yl)propanoic acid	HMDB
(S)-2-Hydroxy-3-(1H-indol-3-yl)propionic acid	HMDB
(S)-Indole-3-lactic acid	HMDB
(AlphaS)-alpha-hydroxy-1H-indole-3-propanoic acid	HMDB
(AlphaS)-alpha-hydroxy-1H-indole-3-propionic acid	HMDB
(ΑS)-α-hydroxy-1H-indole-3-propanoic acid	HMDB
(ΑS)-α-hydroxy-1H-indole-3-propionic acid	HMDB
2-(1H-indol-3-yl)Acetaldehyde	HMDB
2-Hydroxy-3-(1H-indol-3-yl)propanoic acid	HMDB
2-Hydroxy-3-(1H-indol-3-yl)propionic acid	HMDB
2-Hydroxy-3-(3-indolyl)propanoic acid	HMDB
2-Hydroxy-3-(3-indolyl)propionic acid	HMDB
3-(3-Indolyl)-2-hydroxypropanoic acid	HMDB
3-(3-Indolyl)-2-hydroxypropionic acid	HMDB
3-(3-Indolyl)-DL-lactic acid	HMDB
3-Indolyllactic acid	HMDB
Indole-3-L-lactic acid	HMDB
Indole-3-lactic acid	HMDB
L-3-(3-Indolyl)lactic acid	HMDB
L-Indole-3-lactic acid	HMDB
alpha-Hydroxy-1H-indole-3-propanoic acid	HMDB
alpha-Hydroxy-1H-indole-3-propionic acid	HMDB
beta-(3-Indolyl)lactic acid	HMDB
beta-Indolyllactic acid	HMDB
Α-hydroxy-1H-indole-3-propanoic acid	HMDB
Α-hydroxy-1H-indole-3-propionic acid	HMDB
Β-(3-indolyl)lactic acid	HMDB
Β-indolyllactic acid	HMDB
Indolelactic acid	HMDB

Molecular Formula

C₁₁H₁₁NO₃

Average Mass

205.2099

Monoisotopic Mass

205.073893223

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

7417-65-4

SMILES

Not Available

InChI Identifier

InChI=1S/C11H11NO3/c13-10(11(14)15)5-7-6-12-9-4-2-1-3-8(7)9/h1-4,6,10,12-13H,5H2,(H,14,15)/t10-/m0/s1

InChI Key

XGILAAMKEQUXLS-JTQLQIEISA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. Indolyl carboxylic acids and derivatives are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indolyl carboxylic acids and derivatives

Direct Parent

Indolyl carboxylic acids and derivatives

Alternative Parents

Substituents

Indolyl carboxylic acid derivative
3-alkylindole
Indole
Alpha-hydroxy acid
Hydroxy acid
Substituted pyrrole
Benzenoid
Pyrrole
Heteroaromatic compound
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Azacycle
Hydrocarbon derivative
Alcohol
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Not Available

Spectra

Not Available

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Feces
Placenta
Prostate
Urine

Tissue Locations

Placenta
Prostate

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

Multistep Reactions

Reaction ID	Precursor	Product	Enzyme	Reference
MMDBr0012723	L-Tryptophan	3-(indol-3-yl)pyruvic acid	Not Available	Manually annotated by MiMeDB team
MMDBr0012725	3-(indol-3-yl)pyruvic acid	Indolelactic acid	Not Available	Manually annotated by MiMeDB team
MMDBr0012727	Indolelactic acid	Indoleacetic acid	Not Available	Manually annotated by MiMeDB team

Reaction ID	Precursor	Product	Enzyme	Reference
MMDBr0012723	L-Tryptophan	3-(indol-3-yl)pyruvic acid	Not Available	Manually annotated by MiMeDB team
MMDBr0012725	3-(indol-3-yl)pyruvic acid	Indolelactic acid	Not Available	Manually annotated by MiMeDB team
MMDBr0012728	Indolelactic acid	Indole-3-propionate	Not Available	Manually annotated by MiMeDB team

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Alzheimer's disease	decreased	Association	Human plasma	PubMed	33269100
Major depressive disorder	increased	Association	Human serum	PubMed	27832762
Anxiety	increased	Association	Human serum	PubMed	27832762
Parkinson's disease	increased	Association	Human urine	PubMed	25271123
Chronic kidney disease	increased	Association	Human plasma	PubMed	26317986
Aryl hydrocarbon receptor	agonist	Animal_model	Rat PC12 cells (pheochromocytoma of adrenal medulla)	PubMed	32178456
Aryl hydrocarbon receptor	agonist	Cell culture	House mouse AZ-AHR cells (HepG2)	PubMed	32283770

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Firmicutes	3	Human ; Human supragingival plaque; Human feces	Microbial culture; Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Food	Beer	Barley	PubMed	33882831

Source Type	Activity	Data Source	Reference
Drugs	Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox
Domestics	Not Available	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Urine	Detected and Quantified	0.9			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Urine	Detected and Quantified	0.46	0.098	0.98	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Blood	Detected and Quantified	2.8	0.5	5.0	uM	Adult (>18 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Placenta	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Prostate	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Urine	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Urine	Detected but not Quantified					Adult (>18 years old)	Male	Normal	HMDB	22827565
Human Urine	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0000671

DrugBank ID

DB07060

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

676157

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Morita I, Kawamoto M, Yoshida H: Difference in the concentration of tryptophan metabolites between maternal and umbilical foetal blood. J Chromatogr. 1992 May 8;576(2):334-9. doi: 10.1016/0378-4347(92)80208-8. [PubMed:1400722 ]
Morita I, Kawamoto M, Hattori M, Eguchi K, Sekiba K, Yoshida H: Determination of tryptophan and its metabolites in human plasma and serum by high-performance liquid chromatography with automated sample clean-up system. J Chromatogr. 1990 Apr 6;526(2):367-74. doi: 10.1016/s0378-4347(00)82520-7. [PubMed:2361979 ]
Artigas F, Gelpi E: Evaluation of the potential of thermospray liquid chromatography-mass spectrometry in neurochemistry. J Chromatogr. 1987 May 8;394(1):123-34. doi: 10.1016/s0021-9673(01)94166-4. [PubMed:3597614 ]
Salen G, Xu G, Tint GS, Batta AK, Shefer S: Hyperabsorption and retention of campestanol in a sitosterolemic homozygote: comparison with her mother and three control subjects. J Lipid Res. 2000 Nov;41(11):1883-9. [PubMed:11060358 ]
Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
Dodd D, Spitzer MH, Van Treuren W, Merrill BD, Hryckowian AJ, Higginbottom SK, Le A, Cowan TM, Nolan GP, Fischbach MA, Sonnenburg JL: A gut bacterial pathway metabolizes aromatic amino acids into nine circulating metabolites. Nature. 2017 Nov 30;551(7682):648-652. doi: 10.1038/nature24661. Epub 2017 Nov 22. [PubMed:29168502 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Showing metabocard for Indolelactic acid (MMDBc0000135)

MOL for #<Metabolite:0x00007fdaf5abfb08>

3D MOL for #<Metabolite:0x00007fdaf5abfb08>

3D SDF for #<Metabolite:0x00007fdaf5abfb08>

3D-SDF for #<Metabolite:0x00007fdaf5abfb08>

PDB for #<Metabolite:0x00007fdaf5abfb08>

3D PDB for #<Metabolite:0x00007fdaf5abfb08>

SMILES for #<Metabolite:0x00007fdaf5abfb08>

INCHI for #<Metabolite:0x00007fdaf5abfb08>

Structure for #<Metabolite:0x00007fdaf5abfb08>

3D Structure for #<Metabolite:0x00007fdaf5abfb08>