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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:10 UTC
HMDB IDHMDB00671
Secondary Accession NumbersNone
Metabolite Identification
Common NameIndolelactic acid
DescriptionIndolelactic acid is a tryptophan metabolite found in human plasma and serum and normal 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 foetal plasma than in maternal plasma in the protein-bound form. (PMID 2361979 , 1400722 , 3597614 , 11060358 , 1400722 ).
Structure
Thumb
Synonyms
ValueSource
alpha-Hydroxy-1H-indole-3-propanoic acidChEBI
Indole-3-lactic acidChEBI
a-Hydroxy-1H-indole-3-propanoateGenerator
a-Hydroxy-1H-indole-3-propanoic acidGenerator
alpha-Hydroxy-1H-indole-3-propanoateGenerator
α-hydroxy-1H-indole-3-propanoateGenerator
α-hydroxy-1H-indole-3-propanoic acidGenerator
2-Hydroxy-3-(1H-indol-3-yl)propanoateGenerator
Indole-3-lactateGenerator
(+)-2-Hydroxy-3-indol-3-yl-propionateHMDB
(+)-2-Hydroxy-3-indol-3-yl-propionic acidHMDB
(+)-a-Hydroxy-1H-indole-3-propanoateHMDB
(+)-a-Hydroxy-1H-indole-3-propanoic acidHMDB
(+)-a-Hydroxy-1H-indole-3-propionateHMDB
(+)-a-Hydroxy-1H-indole-3-propionic acidHMDB
(+)-alpha-Hydroxy-1H-indole-3-propanoateHMDB
(+)-alpha-Hydroxy-1H-indole-3-propanoic acidHMDB
(+)-alpha-Hydroxy-1H-indole-3-propionateHMDB
(+)-alpha-Hydroxy-1H-indole-3-propionic acidHMDB
(S)-2-Hydroxy-3-indol-3-yl-propionateHMDB
(S)-2-Hydroxy-3-indol-3-yl-propionic acidHMDB
2-Hydroxy-3-indol-3-yl-propionateHMDB
2-Hydroxy-3-indol-3-yl-propionic acidHMDB
2-Hydroxy-3-indol-3-yl-propionsaeureHMDB
DL-3-IndolelactateHMDB
DL-3-Indolelactic acidHMDB
IndolelactateHMDB
Chemical FormulaC11H11NO3
Average Molecular Weight205.2099
Monoisotopic Molecular Weight205.073893223
IUPAC Name2-hydroxy-3-(1H-indol-3-yl)propanoic acid
Traditional Nameindole-3-lactic acid
CAS Registry Number1821-52-9
SMILES
OC(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)
InChI KeyInChIKey=XGILAAMKEQUXLS-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. These 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
  • Indole
  • Benzenoid
  • Substituted pyrrole
  • Hydroxy acid
  • Alpha-hydroxy acid
  • Heteroaromatic compound
  • Pyrrole
  • Secondary alcohol
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity54.55 m3·mol-1ChemAxon
Polarizability20.7 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-001i-0900000000-a73dacebbb4e696069e3View in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0udi-0290000000-fabadc12766d82241f9dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0bti-0950000000-59498880ad7081aa3753View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0159-0900000000-6a8d0e31efc5b93545e6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-015c-2900000000-90fc3496f234f903c6deView in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Prostate
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified2.8 (0.5-5.0) uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
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 QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.9 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot ApplicableAdult (>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 ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022174
KNApSAcK IDNot Available
Chemspider ID83867
KEGG Compound IDC02043
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00671
Metagene LinkHMDB00671
METLIN ID5641
PubChem Compound92904
PDB IDNot Available
ChEBI ID24813
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. 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. [19212411 ]
  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. [2361979 ]
  3. 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. [11060358 ]
  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. [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. [3597614 ]