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Record Information
Version2.0
Created at2022-04-27 22:20:00 UTC
Updated at2022-04-27 22:20:00 UTC
NP-MRD IDNP0050878
Secondary Accession NumbersNone
Natural Product Identification
Common NameHypaphorine
DescriptionLenticin, also known as glyyunnanenine or L-hypaphorine, 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. In plants it is an agonist of the plant hormone indole acetic acid. It is known to be a sleep-inducing compound (PMID: 18571406 ). It can also be detected in blood after an individual has consumed lentils and may therefore serve as a food biomarker. Lenticin is a moderately acidic compound (based on its pKa). Lenticin or hypaphorine is a compound found in lentil extracts. Hypaphorine is found in Abrus precatorius , Caragana sinica, Desmodium gangeticum , Erythrina hypaphorus, Erythrina senegalensis , Erythrina stricta, Erythrina suberosa, Erythrina subumbrans, Erythrina sudumbrans, Erythrina verna, Glycyrrhiza yunnanensis, Hedysarum polybotrys, Maquira coriacea, Pisolithus arhizus and Pterocarpus officinalis . Hypaphorine was first documented in 2000 (PMID: 10659705). Lenticin is an indole alkaloid that is essentially an N-methylated form of tryptophan (PMID: 11089686) (PMID: 11676477) (PMID: 12056802) (PMID: 12236599).
Structure
Thumb
Synonyms
ValueSource
(+)-HypaphorineChEBI
GlyyunnanenineChEBI
L-HypaphorineChEBI
L-Tryptophan betaineChEBI
N,N,N-Trimethyltryptophan betaineChEBI
Tryptophan betaineChEBI
Lenticin nitrateHMDB
HypaforinHMDB
LenticinChEBI
Chemical FormulaC14H18N2O2
Average Mass246.3049 Da
Monoisotopic Mass246.13683 Da
IUPAC Name(2S)-3-(1H-indol-3-yl)-2-(trimethylazaniumyl)propanoate
Traditional Namehypaphorine
CAS Registry NumberNot Available
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
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Abrus precatoriusPlant
Caragana sinicaLOTUS Database
Desmodium gangeticumPlant
Erythrina hypaphorusPlant
Erythrina senegalensisPlant
Erythrina strictaLOTUS Database
Erythrina suberosaLOTUS Database
Erythrina subumbransLOTUS Database
Erythrina sudumbransPlant
Erythrina vernaLOTUS Database
Glycyrrhiza yunnanensisLOTUS Database
Hedysarum polybotrysLOTUS Database
Maquira coriaceaLOTUS Database
Pisolithus arhizusLOTUS Database
Pterocarpus officinalisPlant
Chemical Taxonomy
Description 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
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
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0061115
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
Good Scents IDNot Available
References
General References
  1. Ditengou FA, Lapeyrie F: Hypaphorine from the ectomycorrhizal fungus Pisolithus tinctorius counteracts activities of indole-3-acetic acid and ethylene but not synthetic auxins in eucalypt seedlings. Mol Plant Microbe Interact. 2000 Feb;13(2):151-8. doi: 10.1094/MPMI.2000.13.2.151. [PubMed:10659705 ]
  2. Ditengou FA, Beguiristain T, Lapeyrie F: Root hair elongation is inhibited by hypaphorine, the indole alkaloid from the ectomycorrhizal fungus Pisolithus tinctorius, and restored by indole-3-acetic acid. Planta. 2000 Oct;211(5):722-8. doi: 10.1007/s004250000342. [PubMed:11089686 ]
  3. Kawano T, Kawano N, Hosoya H, Lapeyrie F: Fungal auxin antagonist hypaphorine competitively inhibits indole-3-acetic acid-dependent superoxide generation by horseradish peroxidase. Biochem Biophys Res Commun. 2001 Nov 2;288(3):546-51. doi: 10.1006/bbrc.2001.5800. [PubMed:11676477 ]
  4. Kawano T, Kawano N, Lapeyrie F: A fungal auxin antagonist, hypaphorine prevents the indole-3-acetic acid-dependent irreversible inactivation of horseradish peroxidase: inhibition of Compound III-mediated formation of P-670. Biochem Biophys Res Commun. 2002 Jun 14;294(3):553-9. doi: 10.1016/S0006-291X(02)00513-2. [PubMed:12056802 ]
  5. Reboutier D, Bianchi M, Brault M, Roux C, Dauphin A, Rona JP, Legue V, Lapeyrie F, Bouteau F: The indolic compound hypaphorine produced by ectomycorrhizal fungus interferes with auxin action and evokes early responses in nonhost Arabidopsis thaliana. Mol Plant Microbe Interact. 2002 Sep;15(9):932-8. doi: 10.1094/MPMI.2002.15.9.932. [PubMed:12236599 ]