Showing Compound Gentianine (FDB007359)

Record Information

Version

1.0

Creation date

2010-04-08 22:07:34 UTC

Update date

2019-11-26 03:01:38 UTC

Primary ID

FDB007359

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Gentianine

Description

Gentianine, 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 Number

439-89-4

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
4-(2-Hydroxyethyl)-5-vinylnicotinic acid gamma-lactone	ChEBI
4-(2-Hydroxyethyl)-5-vinylnicotinate g-lactone	Generator
4-(2-Hydroxyethyl)-5-vinylnicotinate gamma-lactone	Generator
4-(2-Hydroxyethyl)-5-vinylnicotinate γ-lactone	Generator
4-(2-Hydroxyethyl)-5-vinylnicotinic acid g-lactone	Generator
4-(2-Hydroxyethyl)-5-vinylnicotinic acid γ-lactone	Generator
5-Ethenyl-3,4-dihydro-1H-pyrano(3,4-c)pyridin-1-one	MeSH
4-(2-hydroxyethyl)-5-vinylnicotinic acid gamma-lactone	biospider
5-ethenyl-3,4-dihydro-1H-pyrano[3,4-c]pyridin-1-one	biospider
From schultesia guianensis malme (mata-zombando)	biospider
Gencianina	biospider
Gentianine	biospider

Predicted Properties

Property	Value	Source
Water Solubility	19.4 g/L	ALOGPS
logP	1.01	ALOGPS
logP	1.34	ChemAxon
logS	-0.96	ALOGPS
pKa (Strongest Basic)	3.01	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	39.19 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	48.92 m³·mol⁻¹	ChemAxon
Polarizability	17.61 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C10H9NO2

IUPAC name

5-ethenyl-1H,3H,4H-pyrano[3,4-c]pyridin-1-one

InChI Identifier

InChI=1S/C10H9NO2/c1-2-7-5-11-6-9-8(7)3-4-13-10(9)12/h2,5-6H,1,3-4H2

InChI Key

DFNZYFAJQPLJFI-UHFFFAOYSA-N

Isomeric SMILES

C=CC1=C2CCOC(=O)C2=CN=C1

Average Molecular Weight

175.184

Monoisotopic Molecular Weight

175.063328537

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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyranopyridines

Sub Class

Not Available

Direct Parent

Pyranopyridines

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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

lactone (CHEBI:28981 )
pyridine alkaloid (CHEBI:28981 )
pyranopyridine (CHEBI:28981 )

Ontology

No ontology term

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Gentianine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0fsj-0900000000-82c909a9b8a7607cde1c	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0900000000-6952936c6079ddf5ab09	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0900000000-d238492324797d68c5ad	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fc0-6900000000-d741083b91716f4a2491	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0900000000-c019889916cceb899160	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0900000000-7551bf35931ac9e53b04	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0ufu-2900000000-909507d1ec10bd79325e	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0900000000-dd76f78fc523efac1e38	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0900000000-ab54bf6cf5b9da2d0589	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-2900000000-eba85c05b3d25808d631	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0900000000-e1e7a7636061f9624da0	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0900000000-6c25d3fbd9a60487381a	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0v4j-9600000000-e569d0287224ee966744	2021-10-21	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

C06525

Pubchem Compound ID

354616

Pubchem Substance ID

Not Available

ChEBI ID

28981

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

GENTIANINE

BIGG ID

Not Available

KNApSAcK ID

C00001977

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
analgesic	35480	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 anaphylactic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti arthritic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti bacterial	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti edemic			DUKE
anti histaminic	37956	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 inflammatory	35472	A substance that reduces or suppresses inflammation.	DUKE
anti meningitic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti psychotic	35476	Antipsychotic drugs are agents that control agitated psychotic behaviour, alleviate acute psychotic states, reduce psychotic symptoms, and exert a quieting effect.	DUKE
anti rheumatic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti shigellic	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti staphylococcic	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti streptococcic	33282	A substance that kills or slows the growth of bacteria.	DUKE
ataractic			DUKE
central nervous system paralytic	35470	A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.	DUKE
central nervous system stimulant	35470	A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.	DUKE
corticosterogenic			DUKE
emetic			DUKE
hypoglycemic	35526	A drug which lowers the blood glucose level.	DUKE
hypotensive			DUKE
myorelaxant			DUKE
neurotoxic	50910	A poison that interferes with the functions of the nervous system.	DUKE
pesticide	25944	Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.	DUKE
sedative	35717	A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.	DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
bitter	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

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).