Indolelactic acid (CHEM021727)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:11:03 UTC
Update Date2016-11-09 01:17:21 UTC
Accession NumberCHEM021727
Identification
Common NameIndolelactic acid
ClassSmall Molecule
DescriptionA hydroxy monocarboxylic acid that is lactic acid substituted by a 1H-indol-3-yl group at position 3. It is a metabolite of tryptophan.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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
Indole-3-lactateGenerator
IndolelactateGenerator
(+)-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
Indole-3-lactic acid, (+-)-isomerHMDB
5-Hydroxyindolepropionic acidHMDB
5-IHIPAHMDB
Chemical FormulaC11H11NO3
Average Molecular Mass205.210 g/mol
Monoisotopic Mass205.074 g/mol
CAS Registry Number1821-52-9
IUPAC Name2-hydroxy-3-(1H-indol-3-yl)propanoic acid
Traditional Nameindole-3-lactic acid
SMILESOC(CC1=CNC2=C1C=CC=C2)C(O)=O
InChI IdentifierInChI=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 KeyXGILAAMKEQUXLS-UHFFFAOYSA-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 Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
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, Positivesplash10-003u-2900000000-bad34fd0864e785e4e97Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0089-5291000000-8b3da0b08dd2ffd4d693Spectrum
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, Positivesplash10-053i-0930000000-fe1fd04d5b4f7d40d608Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01qi-0900000000-7e1de8e44f33e343c791Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f89-0900000000-aa813c26618a596bb9a4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-2590000000-a93dc0fc781357aff735Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0lzl-0910000000-53a7c659337af61dece2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-2900000000-61b91ac21dbc478cbe72Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0000671
FooDB IDFDB022174
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDINDOLE_LACTATE
METLIN ID5641
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID83867
ChEBI ID24813
PubChem Compound ID92904
Kegg Compound IDC02043
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=16347781
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=20540569
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=21749142
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=22372405
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=23111785
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=2361979
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=23924721
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=533277
9. Narayanan, 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.
10. Narayanan, 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.
11. 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.
12. 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.
13. 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.
14. 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.
15. 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.
16. 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.