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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2013-07-22 15:42:19 UTC
Update Date2021-09-14 15:46:16 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
N,N,N-Trimethyltryptophan betaineChEBI
Tryptophan betaineChEBI
Lenticin nitrateHMDB
HypaforinHMDB
LenticinChEBI
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
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
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-186.27830932474
DeepCCS[M+Na]+161.84330932474
AllCCS[M+H]+156.232859911
AllCCS[M+H-H2O]+152.632859911
AllCCS[M+NH4]+159.532859911
AllCCS[M+Na]+160.432859911
AllCCS[M-H]-166.532859911
AllCCS[M+Na-2H]-167.032859911
AllCCS[M+HCOO]-167.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
LenticinC[N+](C)(C)[C@@H](CC1=CNC2=CC=CC=C12)C([O-])=O2977.1Standard polar33892256
LenticinC[N+](C)(C)[C@@H](CC1=CNC2=CC=CC=C12)C([O-])=O1718.8Standard non polar33892256
LenticinC[N+](C)(C)[C@@H](CC1=CNC2=CC=CC=C12)C([O-])=O2232.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Lenticin,1TMS,isomer #1C[N+](C)(C)[C@@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)[O-]2159.5Semi standard non polar33892256
Lenticin,1TMS,isomer #1C[N+](C)(C)[C@@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)[O-]2120.1Standard non polar33892256
Lenticin,1TMS,isomer #1C[N+](C)(C)[C@@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)[O-]2583.3Standard polar33892256
Lenticin,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C=C(C[C@@H](C(=O)[O-])[N+](C)(C)C)C2=CC=CC=C212358.7Semi standard non polar33892256
Lenticin,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C=C(C[C@@H](C(=O)[O-])[N+](C)(C)C)C2=CC=CC=C212336.6Standard non polar33892256
Lenticin,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C=C(C[C@@H](C(=O)[O-])[N+](C)(C)C)C2=CC=CC=C212652.8Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Lenticin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-5890000000-7a32ae6df95ecbe4b4d52017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lenticin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lenticin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lenticin 10V, Positive-QTOFsplash10-0002-0290000000-c42f376f71f6e37252672017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lenticin 20V, Positive-QTOFsplash10-0f7k-0390000000-f1efb195c18ebf5ebaaf2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lenticin 40V, Positive-QTOFsplash10-0f89-0900000000-d8339c908340d1176dc02017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lenticin 10V, Negative-QTOFsplash10-0002-0290000000-4b553f8b8e9e0606e1172017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lenticin 20V, Negative-QTOFsplash10-000b-0890000000-d5d7c7edd0b4db4291602017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lenticin 40V, Negative-QTOFsplash10-014i-0900000000-8c56dbdaac5dc7a92a2e2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lenticin 10V, Negative-QTOFsplash10-0002-0090000000-fdb1f9281332d51496442021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lenticin 20V, Negative-QTOFsplash10-014i-0910000000-a89d64e0d176721c58912021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lenticin 40V, Negative-QTOFsplash10-016r-0900000000-b4ddbcb87a2999e946312021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lenticin 10V, Positive-QTOFsplash10-0udi-0190000000-ec4a6e5db2f844802dc92021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lenticin 20V, Positive-QTOFsplash10-001l-0910000000-0b46677e1ee9ee59d6632021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lenticin 40V, Positive-QTOFsplash10-0006-6900000000-c7a3ff32cff4a5522e4d2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>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
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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 ]
  2. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]