3-[(E)-2-[(5R,6R,8aR)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-decahydronaphthalen-1-yl]ethenyl]-2,5-dihydrofuran-2-one

• ChemBase ID: 179761
• Molecular Formular: C20H28O4
• Molecular Mass: 332.43392
• Monoisotopic Mass: 332.19875938
• SMILES: [C@]12(C([C@@]([C@@H](CC2)O)(CO)C)CCC(=C)C1/C=C/C1=CCOC1=O)C
• Canonical SMILES: OC[C@]1(C)[C@H](O)CC[C@@]2(C1CCC(=C)C2/C=C/C1=CCOC1=O)C
• InChI: InChI=1S/C20H28O4/c1-13-4-7-16-19(2,10-8-17(22)20(16,3)12-21)15(13)6-5-14-9-11-24-18(14)23/h5-6,9,15-17,21-22H,1,4,7-8,10-12H2,2-3H3/b6-5+/t15?,16?,17-,19+,20+/m1/s1
• InChIKey: XMJAJFVLHDIEHF-JMWYYFFJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[(E)-2-[(5R,6R,8aR)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-decahydronaphthalen-1-yl]ethenyl]-2,5-dihydrofuran-2-one
• IUPAC Traditional name: 3-[(E)-2-[(5R,6R,8aR)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-decahydronaphthalen-1-yl]ethenyl]-2,5-dihydrofuran-2-one
• Synonyms: Dehydroandrographolide

Database IDs

• CAS Number: 134418-28-3
• PubChem SID: 164235671
• PubChem CID: 16400335

CALCULATED PROPERTIES

• Acid pKa: 14.394146
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 2.3753035
• LogD (pH = 7.4): 2.3753035
• Log P: 2.3753035
• Molar Refractivity: 94.6856 cm^3
• Polarizability: 36.6591 Å^3
• Polar Surface Area: 66.76 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Product Information

• Biological Source: Constit. of Andrographis paniculata
• Application(s): Hypotensive

REFERENCES

• Pharmacol.Res. (38, No. 6, 413-17, 1998) Cardiovascular activity of 14-deoxy-11,12-didehydroandrographolide in the anaesthetised rat and isolated right atria.