(1S,2S,5S,8R,9S,10S,11R,15S,18R)-9,10,15,18-tetrahydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.15,8.01,11.02,8]octadecan-7-one

• ChemBase ID: 179895
• Molecular Formular: C20H28O6
• Molecular Mass: 364.43272
• Monoisotopic Mass: 364.18858862
• SMILES: [C@@]123[C@]4([C@H]([C@H]5[C@@]([C@@H]2CC[C@@H](C(=C)C1=O)[C@H]3O)(CO4)[C@H](CCC5(C)C)O)O)O
• Canonical SMILES: C=C1[C@@H]2CC[C@@H]3[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-OVFJCENLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,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,^1^1.0^2,^8]octadecan-7-one
• IUPAC Traditional name: (1S,2S,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,^1^1.0^2,^8]octadecan-7-one
• Synonyms: Rubescensin; Rubescensin A; Oridonin

Database IDs

• CAS Number: 28957-04-2
• PubChem SID: 164235805
• PubChem CID: 5321010

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

Pharmacology Properties

• Mechanism of Action: Insect growth inhibitor

Product Information

• Biological Source: Constit. of Isodon trichocarpus, Isodon japonicus and Rabdosia spp.
• Application(s): Also shows antineoplastic activity against Ehrlich ascites carcinoma.; Shows activity against gram-positive bacteria and against Sarcina lutea

REFERENCES

• Fuji, K. et al., Chem. Pharm. Bull., 1989, 37, 1472