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

• ChemBase ID: 160619
• Molecular Formular: C20H30O5
• Molecular Mass: 350.4492
• Monoisotopic Mass: 350.20932406
• SMILES: C1(=C)CC[C@H]2[C@]([C@@H]1C/C=C\1/C(=O)CO[C@H]1O)(CC[C@H]([C@]2(CO)C)O)C
• Canonical SMILES: OC[C@]1(C)[C@H](O)CC[C@@]2([C@@H]1CCC(=C)[C@H]2C/C=C\1/C(=O)CO[C@H]1O)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/h5,14,16-18,21,23-24H,1,4,6-11H2,2-3H3/b13-5-/t14-,16+,17-,18-,19+,20+/m1/s1
• InChIKey: ASLUCFFROXVMFL-QGICXFDVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4E,5R)-4-{2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-decahydronaphthalen-1-yl]ethylidene}-5-hydroxyoxolan-3-one
• IUPAC Traditional name: (4E,5R)-4-{2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-hexahydro-1H-naphthalen-1-yl]ethylidene}-5-hydroxyoxolan-3-one
• Synonyms: (3E,4S)-3-[2-[(1R,4aS,5R,6R,8aS)-Decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenyl]ethylidene]dihydro-4-hydroxy-2(3H)-furanone; [1R-[1α[E(S*)],4aβ,5α,6α,8aα]]-3-[2-[Decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenyl]ethylidene]dihydro-4-hydroxy-2(3H)-furanone; 3α,14,15,18-Tetrahydroxy-5β,9βH,10α-labda-8(20),12-dien-16-oic Acid γ-Lactone; Andrographis; Andrographolid; Andrographolide

Database IDs

• CAS Number: 5508-58-7
• PubChem SID: 162254754
• PubChem CID: 71313401

CALCULATED PROPERTIES

• Acid pKa: 11.638457
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 1.7047089
• LogD (pH = 7.4): 1.7046843
• Log P: 1.7047093
• Molar Refractivity: 95.2333 cm^3
• Polarizability: 37.537582 Å^3
• Polar Surface Area: 86.99 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: White Solid
• Melting Point: 232-235°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - A637475

Andrographolide is a labdane diterpenoid. Andrographolide is the main bioactive component isolated from the medicinal plant Andrographis paniculata. Andrographolide showed significant antihepatotoxic action in P. berghei K173- induced hepatic damage in M.

REFERENCES

• Chander, R. et al.: Int. J. Pharmacog., 33, 135 (1995)
• Chen, H.-W. et al.: J. Nat. Prod., 74, 2408 (1995)
• J. Agric. Food Chem., 59, 5263 (1995)