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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2013-07-22 15:42:19 UTC
Update Date2019-07-23 07:15:47 UTC
HMDB IDHMDB0061115
Secondary Accession Numbers
  • HMDB61115
Metabolite Identification
Common NameLenticin
DescriptionLenticin or hypaphorine is a compound found in lentil extracts. It can also be detected in blood after an individual has consumed lentils and may therefore serve as a food biomarker. Lenticin is an indole alkaloid that is essentially an N-methylated form of tryptophan. It is known to be a sleep-inducing compound (PMID: 18571406 ). In plants it is an agonist of the plant hormone indole acetic acid.
Structure
Data?1563866147
Synonyms
ValueSource
(+)-HypaphorineChEBI
GlyyunnanenineChEBI
L-HypaphorineChEBI
L-Tryptophan betaineChEBI
LenticinChEBI
N,N,N-Trimethyltryptophan betaineChEBI
Tryptophan betaineChEBI
Lenticin nitrateMeSH
HypaforinMeSH
Chemical FormulaC14H18N2O2
Average Molecular Weight246.3049
Monoisotopic Molecular Weight246.13682783
IUPAC Name(2S)-3-(1H-indol-3-yl)-2-(trimethylazaniumyl)propanoate
Traditional Namehypaphorine
CAS Registry Number487-58-1
SMILES
C[N+](C)(C)[C@@H](CC1=CNC2=CC=CC=C12)C([O-])=O
InChI Identifier
InChI=1S/C14H18N2O2/c1-16(2,3)13(14(17)18)8-10-9-15-12-7-5-4-6-11(10)12/h4-7,9,13,15H,8H2,1-3H3/t13-/m0/s1
InChI KeyAOHCBEAZXHZMOR-ZDUSSCGKSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-alpha-amino acids
Alternative Parents
Substituents
  • 3-alkylindole
  • L-alpha-amino acid
  • Indole
  • Indole or derivatives
  • Aralkylamine
  • Substituted pyrrole
  • Benzenoid
  • Tetraalkylammonium salt
  • Pyrrole
  • Heteroaromatic compound
  • Quaternary ammonium salt
  • Carboxylic acid salt
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Amine
  • Organopnictogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organic salt
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0026 g/LALOGPS
logP-0.54ALOGPS
logP-2.2ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)2.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area55.92 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity93.02 m³·mol⁻¹ChemAxon
Polarizability26.6 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-5890000000-7a32ae6df95ecbe4b4d5JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0290000000-c42f376f71f6e3725267JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f7k-0390000000-f1efb195c18ebf5ebaafJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f89-0900000000-d8339c908340d1176dc0JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0290000000-4b553f8b8e9e0606e117JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000b-0890000000-d5d7c7edd0b4db429160JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-0900000000-8c56dbdaac5dc7a92a2eJSpectraViewer | MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer 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 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00001740
Chemspider IDNot Available
KEGG Compound IDC09213
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound442106
PDB IDNot Available
ChEBI ID5832
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Ozawa M, Honda K, Nakai I, Kishida A, Ohsaki A: Hypaphorine, an indole alkaloid from Erythrina velutina, induced sleep on normal mice. Bioorg Med Chem Lett. 2008 Jul 15;18(14):3992-4. doi: 10.1016/j.bmcl.2008.06.002. Epub 2008 Jun 6. [PubMed:18571406 ]