Record Information
Version1.0
Creation date2011-09-21 00:09:33 UTC
Update date2015-10-09 22:29:10 UTC
Primary IDFDB022174
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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) [HMDB]
CAS Number1821-52-9
Structure
Thumb
Synonyms
SynonymSource
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
(+)-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
3-(indol-3-yl)LactateGenerator
3-(indol-3-yl)Lactic acidChEBI
DL-3-indolelactatehmdb
DL-3-indolelactic acidhmdb
Indolelactic acidhmdb
α-hydroxy-1H-indole-3-propanoateGenerator
α-hydroxy-1H-indole-3-propanoic acidGenerator
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
Chemical FormulaC11H11NO3
IUPAC name2-hydroxy-3-(1H-indol-3-yl)propanoic acid
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
Isomeric SMILESOC(CC1=CNC2=C1C=CC=C2)C(O)=O
Average Molecular Weight205.2099
Monoisotopic Molecular Weight205.073893223
Classification
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
Ontology
Disposition

Source:

Biological location:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSIndolelactic acid, 2 TMS, GC-MS Spectrumsplash10-001i-0900000000-a73dacebbb4e696069e3Spectrum
GC-MSIndolelactic acid, 3 TMS, GC-MS Spectrumsplash10-0udi-0290000000-fabadc12766d82241f9dSpectrum
GC-MSIndolelactic acid, non-derivatized, GC-MS Spectrumsplash10-001i-0900000000-a73dacebbb4e696069e3Spectrum
GC-MSIndolelactic acid, non-derivatized, GC-MS Spectrumsplash10-0udi-0290000000-fabadc12766d82241f9dSpectrum
GC-MSIndolelactic acid, non-derivatized, GC-MS Spectrumsplash10-001i-0900000000-026f2953e75b09c74d71Spectrum
GC-MSIndolelactic acid, non-derivatized, GC-MS Spectrumsplash10-0udi-0390000000-f0750c125bcd98a91da9Spectrum
Predicted GC-MSIndolelactic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-003u-2900000000-bad34fd0864e785e4e97Spectrum
Predicted GC-MSIndolelactic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0089-5291000000-8b3da0b08dd2ffd4d693Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0bti-0950000000-59498880ad7081aa37532012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0159-0900000000-6a8d0e31efc5b93545e62012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-015c-2900000000-90fc3496f234f903c6de2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-00lr-0900000000-887bb7e62bbec731a8f72017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-01p9-0900000000-a21984d35288538673d92017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-00lr-0900000000-887bb7e62bbec731a8f72017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-053i-0930000000-fe1fd04d5b4f7d40d6082017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01qi-0900000000-7e1de8e44f33e343c7912017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f89-0900000000-aa813c26618a596bb9a42017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-2590000000-a93dc0fc781357aff7352017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0lzl-0910000000-53a7c659337af61dece22017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-2900000000-61b91ac21dbc478cbe722017-09-01View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
ChemSpider ID83867
ChEMBL IDCHEMBL485011
KEGG Compound IDC02043
Pubchem Compound ID92904
Pubchem Substance IDNot Available
ChEBI ID24813
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00671
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference