(1S,5S,8R,9S,10S,11R,15S,18R)-9,10,15,18-tetrahydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1^{5,8}.0^{1,11}.0^{2,8}]octadecan-7-one

• ChemBase ID: 72966
• Molecular Formular: C20H28O6
• Molecular Mass: 364.43272
• Monoisotopic Mass: 364.18858862
• SMILES: [C@@H]12C(CC[C@@H]([C@]31C1[C@]4([C@]([C@H]2O)(O)OC3)C(=O)C(=C)[C@@H]([C@H]4O)CC1)O)(C)C
• Canonical SMILES: C=C1[C@@H]2CCC3[C@](C1=O)([C@@H]2O)[C@]1(O)OC[C@@]23[C@@H](O)CCC([C@H]2[C@@H]1O)(C)C
• InChI: InChI=1S/C20H28O6/c1-9-10-4-5-11-18-8-26-20(25,19(11,14(9)22)15(10)23)16(24)13(18)17(2,3)7-6-12(18)21/h10-13,15-16,21,23-25H,1,4-8H2,2-3H3/t10?,11?,12-,13+,15+,16-,18+,19-,20+/m0/s1
• InChIKey: SDHTXBWLVGWJFT-HILOZQTFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,5S,8R,9S,10S,11R,15S,18R)-9,10,15,18-tetrahydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1^{5,8}.0^{1,11}.0^{2,8}]octadecan-7-one
• IUPAC Traditional name: (1S,5S,8R,9S,10S,11R,15S,18R)-9,10,15,18-tetrahydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1^{5,8}.0^{1,11}.0^{2,8}]octadecan-7-one
• Synonyms: Isodonol; Oridonin

Database IDs

• CAS Number: 28957-04-2
• PubChem SID: 162037886
• PubChem CID: 49867940

CALCULATED PROPERTIES

• Acid pKa: 10.51331
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): 0.540604
• LogD (pH = 7.4): 0.5402741
• Log P: 0.54060817
• Molar Refractivity: 91.8773 cm^3
• Polarizability: 37.001152 Å^3
• Polar Surface Area: 107.22 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Condition: -20°C

Product Information

• Salt Data: Free Base

DETAILS

Selleck Chemicals - S2335

Research Area: Cancer
Biological Activity:
Oridonin(Isodonol), an entkaurane diterpenoid isolated from Rabdosia rubescens, is an important traditional Chinese herbal remedy. Studies showed that oridonin induced apoptosis in a variety of cancer cells including those from prostate,breast, non-small cell lung cancer, acute leukemia, glioblastoma multiforme and human melanoma cells. Cell culture experiments have indicated that oridonin inhibits cell cycle progression and induces apoptosis as well as enhance the phagocytosis of apoptotic cells by macrophages. Oridonin has also immunosuppressive properties both in vitro and in vivo. [1]

REFERENCES

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