Record Information
Version1.0
Creation date2010-04-08 22:07:34 UTC
Update date2018-05-29 00:41:32 UTC
Primary IDFDB007359
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameGentianine
DescriptionGentianine, also known as 4-(2-hydroxyethyl)-5-vinylnicotinate g-lactone, is a member of the class of compounds known as pyranopyridines. Pyranopyridines are polycyclic aromatic compounds containing a pyran ring fused to a pyridine ring. Gentianine is soluble (in water) and a strong basic compound (based on its pKa). Gentianine is a bitter tasting compound found in fenugreek, which makes gentianine a potential biomarker for the consumption of this food product.
CAS Number439-89-4
Structure
Thumb
Synonyms
SynonymSource
4-(2-Hydroxyethyl)-5-vinylnicotinic acid gamma-lactoneChEBI
4-(2-Hydroxyethyl)-5-vinylnicotinate g-lactoneGenerator
4-(2-Hydroxyethyl)-5-vinylnicotinate gamma-lactoneGenerator
4-(2-Hydroxyethyl)-5-vinylnicotinate γ-lactoneGenerator
4-(2-Hydroxyethyl)-5-vinylnicotinic acid g-lactoneGenerator
4-(2-Hydroxyethyl)-5-vinylnicotinic acid γ-lactoneGenerator
4-(2-hydroxyethyl)-5-vinylnicotinic acid gamma-lactonebiospider
5-ethenyl-3,4-dihydro-1H-pyrano[3,4-c]pyridin-1-onebiospider
From schultesia guianensis malme (mata-zombando)biospider
Gencianinabiospider
Gentianinebiospider
Predicted Properties
PropertyValueSource
Water Solubility19.4 g/LALOGPS
logP1.01ALOGPS
logP1.34ChemAxon
logS-0.96ALOGPS
pKa (Strongest Basic)3.01ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area39.19 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity48.92 m³·mol⁻¹ChemAxon
Polarizability17.61 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC10H9NO2
IUPAC name5-ethenyl-1H,3H,4H-pyrano[3,4-c]pyridin-1-one
InChI IdentifierInChI=1S/C10H9NO2/c1-2-7-5-11-6-9-8(7)3-4-13-10(9)12/h2,5-6H,1,3-4H2
InChI KeyDFNZYFAJQPLJFI-UHFFFAOYSA-N
Isomeric SMILESC=CC1=C2CCOC(=O)C2=CN=C1
Average Molecular Weight175.184
Monoisotopic Molecular Weight175.063328537
Classification
DescriptionThis compound belongs to the class of organic compounds known as pyranopyridines. These are polycyclic aromatic compounds containing a pyran ring fused to a pyridine ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyranopyridines
Sub ClassNot Available
Direct ParentPyranopyridines
Alternative Parents
Substituents
  • Pyranopyridine
  • Pyridine carboxylic acid
  • Pyridine
  • Heteroaromatic compound
  • Lactone
  • Carboxylic acid ester
  • Oxacycle
  • Azacycle
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
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
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fsj-0900000000-82c909a9b8a7607cde1cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-6952936c6079ddf5ab09JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0900000000-d238492324797d68c5adJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fc0-6900000000-d741083b91716f4a2491JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-c019889916cceb899160JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0900000000-7551bf35931ac9e53b04JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ufu-2900000000-909507d1ec10bd79325eJSpectraViewer
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC06525
Pubchem Compound ID354616
Pubchem Substance IDNot Available
ChEBI ID28981
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDGENTIANINE
BIGG IDNot Available
KNApSAcK IDC00001977
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 / Bioactivities
DescriptorIDDefinitionReference
analgesic35480 An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.DUKE
anti anaphylactic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti arthritic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti edemicDUKE
anti histaminic37956 Histamine antagonists are the drugs that bind to but do not activate histamine receptors, thereby blocking the actions of histamine or histamine agonists.DUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
anti meningitic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti psychotic35476 Antipsychotic drugs are agents that control agitated psychotic behaviour, alleviate acute psychotic states, reduce psychotic symptoms, and exert a quieting effect.DUKE
anti rheumatic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti shigellic33282 A substance that kills or slows the growth of bacteria.DUKE
anti staphylococcic33282 A substance that kills or slows the growth of bacteria.DUKE
anti streptococcic33282 A substance that kills or slows the growth of bacteria.DUKE
ataracticDUKE
central nervous system paralytic35470 A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.DUKE
central nervous system stimulant35470 A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.DUKE
corticosterogenicDUKE
emeticDUKE
hypoglycemic35526 A drug which lowers the blood glucose level.DUKE
hypotensiveDUKE
myorelaxantDUKE
neurotoxic50910 A poison that interferes with the functions of the nervous system.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
sedative35717 A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
bitter
  1. Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).