Record Information
Version1.0
Creation date2010-04-08 22:13:29 UTC
Update date2019-11-26 03:15:39 UTC
Primary IDFDB018064
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameL-N-(1H-Indol-3-ylacetyl)glutamic acid
DescriptionL-N-(1H-Indol-3-ylacetyl)glutamic acid, also known as (indole-3-acetyl)glutamate, belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. L-N-(1H-Indol-3-ylacetyl)glutamic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). L-N-(1H-Indol-3-ylacetyl)glutamic acid has been detected, but not quantified in, pulses. This could make L-N-(1H-indol-3-ylacetyl)glutamic acid a potential biomarker for the consumption of these foods.
CAS Number57105-48-3
Structure
Thumb
Synonyms
SynonymSource
(Indole-3-acetyl)glutamic acidChEBI
N-(indol-3-Ylacetyl)glutamic acidChEBI
(Indole-3-acetyl)glutamateGenerator
N-(indol-3-Ylacetyl)glutamateGenerator
L-N-(1H-indol-3-Ylacetyl)glutamateGenerator
S-N-(1H-indol-3-Ylacetyl)glutamic acidHMDB
N-(Indole-3-acetyl)glutamateGenerator
L-N-(1H-Indol-3-ylacetyl)glutamic acidmanual
N-(1H-Indol-3-ylacetyl)glutamic acid, 9CI; L-formdb_source
S-N-(1H-Indol-3-ylacetyl)glutamic acidmanual
Predicted Properties
PropertyValueSource
Water Solubility0.19 g/LALOGPS
logP1.08ALOGPS
logP0.82ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)3.65ChemAxon
pKa (Strongest Basic)-2.4ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area119.49 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity76.54 m³·mol⁻¹ChemAxon
Polarizability30.15 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC15H16N2O5
IUPAC name2-[2-(1H-indol-3-yl)acetamido]pentanedioic acid
InChI IdentifierInChI=1S/C15H16N2O5/c18-13(17-12(15(21)22)5-6-14(19)20)7-9-8-16-11-4-2-1-3-10(9)11/h1-4,8,12,16H,5-7H2,(H,17,18)(H,19,20)(H,21,22)
InChI KeyYRKLGWOHYXIKSF-UHFFFAOYSA-N
Isomeric SMILESOC(=O)CCC(NC(=O)CC1=CNC2=C1C=CC=C2)C(O)=O
Average Molecular Weight304.2979
Monoisotopic Molecular Weight304.105921632
Classification
Description Belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentGlutamic acid and derivatives
Alternative Parents
Substituents
  • Glutamic acid or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • 3-alkylindole
  • Indole
  • Indole or derivatives
  • Dicarboxylic acid or derivatives
  • Substituted pyrrole
  • Benzenoid
  • Pyrrole
  • Heteroaromatic compound
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid
  • Azacycle
  • Organoheterocyclic compound
  • Carbonyl group
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 59.21%; H 5.30%; N 9.21%; O 26.29%DFC
Melting PointMp 162.5° dec.DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]27D -10.57 (H2O)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSL-N-(1H-Indol-3-ylacetyl)glutamic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a59-2940000000-09d09a217ae708fac247Spectrum
Predicted GC-MSL-N-(1H-Indol-3-ylacetyl)glutamic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001i-4918100000-6bc4f4e9867ed36188b5Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4s-0983000000-2866d0ee89f977b0a658Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zgi-0920000000-dc9aa8ba5109e46f7a4dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ue9-2900000000-74a4c83a7429e45b064bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zfr-0469000000-79dff4dcec01d9efc641Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0961000000-97ece0f8058fdccb65f8Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014l-5900000000-96382acfa3823ff6515fSpectrum
NMRNot Available
ChemSpider ID28567151
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID25200809
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB38665
CRC / DFC (Dictionary of Food Compounds) IDLFG45-S:LFG46-T
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
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference