(3E)-3-{2-[(5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-decahydronaphthalen-1-yl]ethylidene}-4-hydroxyoxolan-2-one

• ChemBase ID: 179774
• Molecular Formular: C20H30O5
• Molecular Mass: 350.4492
• Monoisotopic Mass: 350.20932406
• SMILES: [C@]12(C([C@@]([C@@H](CC2)O)(CO)C)CCC(=C)C1C/C=C\1/C(=O)OCC1O)C
• Canonical SMILES: OC[C@]1(C)[C@H](O)CC[C@@]2(C1CCC(=C)C2C/C=C/1\C(O)COC1=O)C
• InChI: InChI=1S/C20H30O5/c1-12-4-7-16-19(2,9-8-17(23)20(16,3)11-21)14(12)6-5-13-15(22)10-25-18(13)24/h5,14-17,21-23H,1,4,6-11H2,2-3H3/b13-5+/t14?,15?,16?,17-,19+,20+/m1/s1
• InChIKey: BOJKULTULYSRAS-LOJHQVBKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3E)-3-{2-[(5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-decahydronaphthalen-1-yl]ethylidene}-4-hydroxyoxolan-2-one
• IUPAC Traditional name: (3E)-3-{2-[(5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-decahydronaphthalen-1-yl]ethylidene}-4-hydroxyoxolan-2-one
• Synonyms: Andrographolide

Database IDs

• CAS Number: 5508-58-7
• PubChem SID: 164235684
• PubChem CID: 16406675

CALCULATED PROPERTIES

• Acid pKa: 13.477876
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 1.6623217
• LogD (pH = 7.4): 1.6623213
• Log P: 1.6623217
• Molar Refractivity: 94.9305 cm^3
• Polarizability: 37.537582 Å^3
• Polar Surface Area: 86.99 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Activator of alpha-1A-adrenoceptor; Prevents oxygen radical production by human neutrophils; Suppressor of the expression of inducible nitric oxide synthase

Product Information

• Biological Source: Constit. of Andrographis paniculata
• Application(s): Cardioprotective; Hepatoprotective; Shown to be effective against certain cancers and is an effective purgative

REFERENCES

• Habtemariam, S. et al., Phytother. Res., 1998, 12, 37-40, (Andrographolide, activity)
• Singh, M. et al., Planta Med., 1999, 65, 2-8, (review)
• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 1, 1135C, (nmr)
• Talukdar, P.B. et al., Indian J. Chem., 1968, 6, 252, (isol)
• Patra, A. et al., Org. Magn. Reson., 1981, 16, 74; 17, 301, (cmr)
• Fujita, T. et al., Chem. Pharm. Bull., 1984, 32, 2117, (cryst struct)
• Matsuda, T. et al., Chem. Pharm. Bull., 1994, 42, 1216-1225, (isol, pmr, cmr, activity)