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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-06-15 17:04:51 UTC
HMDB IDHMDB0000671
Secondary Accession Numbers
  • HMDB00671
Metabolite Identification
Common NameIndolelactic acid
DescriptionIndolelactic 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
Data?1582752148
Synonyms
ValueSource
3-(indol-3-yl) LACTic acidGenerator
(2S)-2-Hydroxy-3-(1H-indol-3-yl)propanoic acidHMDB
(2S)-2-Hydroxy-3-(1H-indol-3-yl)propionic acidHMDB
(2S)-2-Hydroxy-3-indoylpropanoic acidHMDB
(2S)-2-Hydroxy-3-indoylpropionic acidHMDB
(S)-2-Hydroxy-3-(1H-indol-3-yl)propanoic acidHMDB
(S)-2-Hydroxy-3-(1H-indol-3-yl)propionic acidHMDB
(S)-Indole-3-lactic acidHMDB
(alphaS)-alpha-Hydroxy-1H-indole-3-propanoic acidHMDB
(alphaS)-alpha-Hydroxy-1H-indole-3-propionic acidHMDB
(αS)-α-Hydroxy-1H-indole-3-propanoic acidHMDB
(αS)-α-Hydroxy-1H-indole-3-propionic acidHMDB
2-(1H-Indol-3-yl)acetaldehydeHMDB
2-Hydroxy-3-(1H-indol-3-yl)propanoic acidHMDB
2-Hydroxy-3-(1H-indol-3-yl)propionic acidHMDB
2-Hydroxy-3-(3-indolyl)propanoic acidHMDB
2-Hydroxy-3-(3-indolyl)propionic acidHMDB
3-(3-Indolyl)-2-hydroxypropanoic acidHMDB
3-(3-Indolyl)-2-hydroxypropionic acidHMDB
3-(3-Indolyl)-DL-lactic acidHMDB
3-Indolyllactic acidHMDB
Indole-3-L-lactic acidHMDB
Indole-3-lactic acidHMDB
Indolelactic acidHMDB
L-3-(3-Indolyl)lactic acidHMDB
L-Indole-3-lactic acidHMDB
alpha-Hydroxy-1H-indole-3-propanoic acidHMDB
alpha-Hydroxy-1H-indole-3-propionic acidHMDB
beta-(3-Indolyl)lactic acidHMDB
beta-Indolyllactic acidHMDB
α-Hydroxy-1H-indole-3-propanoic acidHMDB
α-Hydroxy-1H-indole-3-propionic acidHMDB
β-(3-Indolyl)lactic acidHMDB
β-Indolyllactic acidHMDB
Chemical FormulaC11H11NO3
Average Molecular Weight205.2099
Monoisotopic Molecular Weight205.073893223
IUPAC Name(2S)-2-hydroxy-3-(1H-indol-3-yl)propanoic acid
Traditional Name3-(indol-3-yl) lactate
CAS Registry Number7417-65-4
SMILES
O[C@@H](CC1=CNC2=C1C=CC=C2)C(O)=O
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 KeyXGILAAMKEQUXLS-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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndolyl carboxylic acids and derivatives
Direct ParentIndolyl 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 FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility17 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.12 g/LALOGPS
logP1.33ALOGPS
logP1.28ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)4.14ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area73.32 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity54.55 m³·mol⁻¹ChemAxon
Polarizability20.7 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-001i-0900000000-a73dacebbb4e696069e3Spectrum
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0udi-0290000000-fabadc12766d82241f9dSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001i-0900000000-a73dacebbb4e696069e3Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0udi-0290000000-fabadc12766d82241f9dSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-001i-0900000000-026f2953e75b09c74d71Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-0390000000-f0750c125bcd98a91da9Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-053f-3900000000-518956592de7aaad712fSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0bti-0950000000-59498880ad7081aa3753Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0159-0900000000-6a8d0e31efc5b93545e6Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-015c-2900000000-90fc3496f234f903c6deSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-00lr-0900000000-887bb7e62bbec731a8f7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-01p9-0900000000-a21984d35288538673d9Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00lr-0900000000-887bb7e62bbec731a8f7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0bu9-0930000000-eb637fab2d892b6f884bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01q9-0900000000-71208d388abba707ce94Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900000000-11da08a6a64282a294a3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-3590000000-4f5f452c037ff1151799Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0m8c-2910000000-63debafc3bcaff103bddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-4900000000-ab106b4b81c99f1d7ebdSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Placenta
  • Prostate
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified2.8 (0.5-5.0) uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.46 (0.098-0.98) umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
details
UrineDetected but not Quantified Adult (>18 years old)Both
Normal
details
UrineDetected but not Quantified Adult (>18 years old)Male
Normal
details
UrineDetected and Quantified0.9 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
UrineDetected but not Quantified Adult (>18 years old)FemaleEpithelial ovarian cancer details
UrineDetected and Quantified322.045 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Gastroesophageal reflux disease
    • Mordechai, Hien, ...
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDDB07060
Phenol Explorer Compound IDNot Available
FooDB IDFDB022174
KNApSAcK IDNot Available
Chemspider ID588900
KEGG Compound IDC02043
BioCyc IDINDOLE_LACTATE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound676157
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNarayanan, T. K.; Rao, G. Ramananda. Beta-indoleethanol and beta-indolelactic acid production by Candida species: Their antibacterial and autoantibiotic action. Antimicrobial Agents and Chemotherapy (1976), 9(3), 375-80.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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 ]
  2. 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. [PubMed:2361979 ]
  3. 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 ]
  4. 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. [PubMed:1400722 ]
  5. 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. [PubMed:3597614 ]
  6. 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 ]
  7. 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 ]