(1R,2S,6R,10S,11R,13S,15R)-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.02,6.011,13]pentadeca-3,8-dien-13-yl acetate

• ChemBase ID: 177076
• Molecular Formular: C22H30O6
• Molecular Mass: 390.47
• Monoisotopic Mass: 390.20423868
• SMILES: [C@@H]12[C@](CC(=C[C@@H]3[C@@]1([C@@H](C[C@@]1([C@H]3C1(C)C)OC(=O)C)C)O)CO)(C(=O)C(=C2)C)O
• Canonical SMILES: OCC1=C[C@H]2[C@H]3[C@@](C3(C)C)(OC(=O)C)C[C@H]([C@@]2([C@H]2[C@@](C1)(O)C(=O)C(=C2)C)O)C
• InChI: InChI=1S/C22H30O6/c1-11-6-16-20(26,18(11)25)9-14(10-23)7-15-17-19(4,5)21(17,28-13(3)24)8-12(2)22(15,16)27/h6-7,12,15-17,23,26-27H,8-10H2,1-5H3/t12-,15+,16-,17?,20-,21+,22-/m1/s1
• InChIKey: BOJKFRKNLSCGHY-KUHYLXMHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,6R,10S,11R,13S,15R)-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0^2,^6.0^1^1,^1^3]pentadeca-3,8-dien-13-yl acetate
• IUPAC Traditional name: prostratin
• Synonyms: (1aR,1bS,4aR,7aS,7bR,8R,9aS)-9a-(Acetyloxy)-1,1a,1b,4,4a,7a,7b,8,9,9a-decahydro-4a,7b-dihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5H-cyclopropa[3,4]benz[1,2-e]azulen-5-one; 12-Deoxyphorbol 13-acetate; 13-O-Acetylphorbol; NSC 623310; Stillingia Factor S7; Prostratin

Database IDs

• CAS Number: 60857-08-1
• PubChem SID: 164232986
• PubChem CID: 454217

CALCULATED PROPERTIES

• Acid pKa: 12.574634
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 0.6935895
• LogD (pH = 7.4): 0.69358665
• Log P: 0.69358957
• Molar Refractivity: 103.6662 cm^3
• Polarizability: 40.592663 Å^3
• Polar Surface Area: 104.06 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - P838800

It is a protein kinase C activator found in the bark of the mamala tree of Samoa, Homalanthus nutans (Euphorbiaceae). Research indicated that prostratin has potential to be useful in the treatment of HIV as it flushes viral reservoirs in latently infecte

REFERENCES

• Reuben, et al.: Clin. Cancer Res., 6, 1671 (2000)
• Korin, Y., et al.: J. Virol., 76, 8118 (2000)
• Wei, X., et al.: Nature, 422, 307 (2000)
• Kutsch, O., et al.: Antimicrob. Agents Chemother., 48, 1652 (2000)