Record Information
Version1.0
Creation date2010-04-08 22:07:34 UTC
Update date2025-11-18 23:04:43 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
5-Ethenyl-3,4-dihydro-1H-pyrano(3,4-c)pyridin-1-oneMeSH
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
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
Description 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
  • Carboxylic acid ester
  • Lactone
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Oxacycle
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSGentianine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0fsj-0900000000-82c909a9b8a7607cde1cSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-6952936c6079ddf5ab092016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0900000000-d238492324797d68c5ad2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fc0-6900000000-d741083b91716f4a24912016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-c019889916cceb8991602016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0900000000-7551bf35931ac9e53b042016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ufu-2900000000-909507d1ec10bd79325e2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-dd76f78fc523efac1e382021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0900000000-ab54bf6cf5b9da2d05892021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-2900000000-eba85c05b3d25808d6312021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-e1e7a7636061f9624da02021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0900000000-6c25d3fbd9a60487381a2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0v4j-9600000000-e569d0287224ee9667442021-10-21View Spectrum
NMRNot Available
ChemSpider ID314782
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 that relieves pain by reducing or blocking pain signals in the brain, commonly used to manage acute or chronic pain, inflammation, and fever, with therapeutic applications in surgery, injury, and disease treatment.DUKE
Anti-anaphylactic52217 An agent that prevents or treats anaphylaxis, a severe allergic reaction. It plays a biological role in stabilizing mast cells and reducing histamine release. Therapeutically, it is used to manage allergic emergencies, with key medical applications including treatment of anaphylactic shock, asthma, and allergic rhinitis.DUKE
Anti-arthritic52217 An agent that reduces joint inflammation and alleviates symptoms of arthritis, commonly used in managing rheumatoid arthritis, osteoarthritis, and other inflammatory joint disorders, to improve mobility and quality of life.DUKE
Anti bacterial33282 An agent that inhibits the growth of or destroys bacteria, playing a crucial role in preventing and treating infections. Therapeutically, it is used to combat bacterial infections, with key medical applications including treating pneumonia, tuberculosis, and skin infections, as well as preventing surgical site infections and sepsis.DUKE
Anti-edemicAn agent that relieves or prevents edema, reducing abnormal fluid accumulation in tissues or the circulatory system, commonly used to treat conditions such as swelling, inflammation, and water retention.DUKE
Anti histaminic37956 An agent that blocks histamine receptors, reducing allergic symptoms. Therapeutically, it alleviates itching, sneezing, and runny nose, commonly used in managing allergies, itching, and hives, as well as treating conditions like anaphylaxis and allergic rhinitis.DUKE
Anti-inflammatory35472 An agent that reduces inflammation, playing a biological role in suppressing immune responses and therapeutic applications in managing pain, swelling, and redness. Key medical uses include treating arthritis, allergies, and autoimmune disorders, as well as relieving symptoms of conditions such as asthma and dermatitis.DUKE
Anti-meningitic52217 An agent that combats meningitis, reducing inflammation and infection in the meninges. Therapeutically, it's used to treat bacterial, viral, or fungal meningitis, and its key medical applications include preventing complications, such as brain damage, and promoting recovery in affected patients.DUKE
Anti psychotic35476 An agent that reduces psychotic symptoms, commonly used in managing schizophrenia, bipolar disorder, and other mental health conditions by blocking dopamine receptors in the brain, thereby alleviating hallucinations, delusions, and disordered thinking.DUKE
Anti-rheumatic52217 An agent that reduces inflammation and alleviates symptoms of rheumatic diseases, such as arthritis. It plays a biological role in modulating the immune system and inhibiting pro-inflammatory pathways. Therapeutically, anti-rheumatics are used to manage conditions like rheumatoid arthritis, lupus, and osteoarthritis, reducing pain, swelling, and joint damage. Key medical uses include slowing disease progression and improving quality of life for patients with chronic rheumatic conditions.DUKE
Anti-shigellic33282 An agent that combats Shigella infections, reducing bacterial growth and alleviating symptoms of shigellosis, a highly contagious diarrheal disease. Therapeutically, it is used to treat gastrointestinal infections, preventing dehydration and promoting recovery, particularly in pediatric and immunocompromised patients.DUKE
Anti-staphylococcic33282 An agent that combats Staphylococcus infections, playing a crucial role in preventing bacterial growth. Therapeutically, it is used to treat skin and soft tissue infections, respiratory tract infections, and bloodstream infections. Key medical uses include treating methicillin-resistant Staphylococcus aureus (MRSA) and other staphylococcal infections, reducing the risk of infection and promoting wound healing.DUKE
Anti-streptococcic33282 An agent that targets and combats Streptococcus bacteria, reducing infection and inflammation. Therapeutically, it is used to treat streptococcal infections, such as strep throat and skin infections, and to prevent complications like rheumatic fever.DUKE
AtaracticAn agent that has a tranquilizing effect, reducing anxiety and stress. Its biological role involves modulating neurotransmitter activity to calm the nervous system. Therapeutically, it is used as an anxiolytic, commonly applied in managing anxiety disorders, insomnia, and restlessness, promoting relaxation and emotional balance.DUKE
Central nervous system paralytic35470 An agent that disrupts neural transmission, causing muscle relaxation and paralysis. Its biological role involves blocking nerve impulses, and its therapeutic applications include managing seizures, muscle spasms, and anesthesia. Key medical uses include surgical procedures, intensive care, and treatment of tetanus and strychnine poisoning.DUKE
Central nervous system stimulant35470 An agent that increases alertness and activity by enhancing neurotransmitter release, used therapeutically to manage attention deficit hyperactivity disorder (ADHD), narcolepsy, and fatigue, and to improve cognitive function and mood.DUKE
CorticosterogenicAn agent that stimulates corticosterone production, a steroid hormone produced in the adrenal glands. It plays a biological role in stress response and regulating metabolism. Therapeutically, it has applications in managing adrenal insufficiency and certain inflammatory conditions, with key medical uses in veterinary medicine, particularly in rodents and non-human animals.DUKE
EmeticAn agent that induces vomiting, playing a biological role in expelling toxins from the body. Therapeutically, it is used to treat poisoning, overdose, or gastrointestinal obstruction. Key medical uses include managing drug toxicity and aiding in stomach pumping procedures.DUKE
Hypoglycemic35526 An agent that lowers blood glucose levels, playing a crucial role in glucose metabolism. Therapeutically, it is used to manage diabetes and insulin resistance, with key medical applications in treating type 1 and 2 diabetes, and preventing diabetic complications.DUKE
HypotensiveAn agent that lowers blood pressure, playing a biological role in regulating cardiovascular function. Therapeutically, it's used to manage hypertension, heart failure, and angina, with key medical applications in preventing stroke, kidney disease, and cardiac complications.DUKE
MyorelaxantAn agent that reduces muscle contractility by blocking nerve impulses or decreasing motor end plate excitability, used therapeutically to relieve muscle spasms, tension, and pain, commonly in managing musculoskeletal disorders, anxiety, and insomnia.DUKE
Neurotoxic50910 A substance that damages or destroys nerve cells, disrupting normal brain function. It has no therapeutic applications, but is used in research to study neurodegenerative diseases. Key medical uses include understanding and developing treatments for conditions like Alzheimer's and Parkinson's diseases, where neurotoxicity plays a role.DUKE
Pesticide25944 An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.DUKE
Sedative35717 An agent that calms nervous activity, reducing anxiety and inducing relaxation. Its biological role is to slow down brain function, promoting sleep and relieving stress. Therapeutically, sedatives are used to manage insomnia, anxiety disorders, and seizures, as well as to prepare patients for medical procedures.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).