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

• ChemBase ID: 179753
• Molecular Formular: C10H9NO2
• Molecular Mass: 175.18396
• Monoisotopic Mass: 175.06332853
• SMILES: c12C(=O)OCCc1c(C=C)cnc2
• Canonical SMILES: C=Cc1cncc2c1CCOC2=O
• InChI: InChI=1S/C10H9NO2/c1-2-7-5-11-6-9-8(7)3-4-13-10(9)12/h2,5-6H,1,3-4H2
• InChIKey: DFNZYFAJQPLJFI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-ethenyl-1H,3H,4H-pyrano[3,4-c]pyridin-1-one
• IUPAC Traditional name: 5-ethenyl-1H,3H,4H-pyrano[3,4-c]pyridin-1-one; gentianine
• Synonyms: 4-(2-Hydroxyethyl)-5-vinylnicotinic lactone; Erythricine; Gentianine

Database IDs

• CAS Number: 439-89-4
• PubChem SID: 164235663
• PubChem CID: 354616

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.3343794
• LogD (pH = 7.4): 1.335625
• Log P: 1.3356409
• Molar Refractivity: 48.9223 cm^3
• Polarizability: 18.477867 Å^3
• Polar Surface Area: 39.19 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Powder

Pharmacology Properties

• Mechanism of Action: Suppressor of TNF-alpha and IL-6 production

Product Information

• Purity: 98.0
• Biological Source: Alkaloid from Gentiana kirilowi and very many other Gentiana spp., from several Swertia spp. and several other genera in Gentianaceae. Also found in Strychnos angolensis and other Strychnos spp.
• Application(s): Antiinflammator; Hypotensive

REFERENCES

• Proskurnina, N.F., J. Gen. Chem. USSR (Engl. Transl.), 1944, 14, 1148; CA, 40, 7213, (isol, struct)
• Govindachari, T.R. et al., J.C.S., 1957, 551; 2725, (isol, struct, uv, synth)
• Lavie, D. et al., Chem. Ind. (London), 1963, 781, (uv, ir, pmr)
• Bailleul, F. et al., Phytochemistry, 1977, 16, 723, (cmr)
• Delaude, C. et al., Bull. Soc. R. Sci. Liege, 1997, 66, 183-286, (occur, Strychnos)