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

• ChemBase ID: 72918
• Molecular Formular: C20H30O5
• Molecular Mass: 350.4492
• Monoisotopic Mass: 350.20932406
• SMILES: [C@@H]1([C@]([C@@H]2[C@@](CC1)([C@@H](C(=C)CC2)C/C=C\1/C(=O)OCC1O)C)(CO)C)O
• Canonical SMILES: OC[C@]1(C)[C@H](O)CC[C@@]2([C@@H]1CCC(=C)[C@H]2C/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-NXIQKPQYSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 5508-58-7
• PubChem SID: 162037838
• PubChem CID: 15922990

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

Safety Information

• Storage Condition: -20°C

Product Information

• Salt Data: Free Base

DETAILS

Selleck Chemicals - S2261

Research Area: Cancer
Biological Activity:
Andrographolide is a labdane diterpenoid that is the main bioactive component of the medicinal plant Andrographis paniculata. [1] It is an extremely bitter substance extracted from the stem and leaves of the andrographis paniculata, which is grown for medicinal purposes in China and India. It has been shown to be effective against certain cancers and is an effective purgative. [2]

REFERENCES

• http://en.wikipedia.org/wiki/Andrographolide