[(1S,2S,6R,10S,11R,13S,14R,15R)-13-(acetyloxy)-1,6-dihydroxy-4,12,12,15-tetramethyl-5-oxo-14-[(2-phenylacetyl)oxy]tetracyclo[8.5.0.02,6.011,13]pentadeca-3,8-dien-8-yl]methyl 2-(4-hydroxy-3-methoxyphenyl)acetate

• ChemBase ID: 133485
• Molecular Formular: C39H44O11
• Molecular Mass: 688.76006
• Monoisotopic Mass: 688.28836223
• SMILES: C[C@@H]1[C@H]([C@@]2([C@@H](C2(C)C)[C@H]2[C@]1([C@@H]1C=C(C(=O)[C@]1(CC(=C2)COC(=O)Cc1ccc(c(c1)OC)O)O)C)O)OC(=O)C)OC(=O)Cc1ccccc1
• Canonical SMILES: COc1cc(ccc1O)CC(=O)OCC1=C[C@H]2[C@@H]3C([C@]3(OC(=O)C)[C@@H]([C@H]([C@@]2([C@H]2[C@@](C1)(O)C(=O)C(=C2)C)O)C)OC(=O)Cc1ccccc1)(C)C
• InChI: InChI=1S/C39H44O11/c1-21-14-30-37(45,34(21)44)19-26(20-48-31(42)18-25-12-13-28(41)29(16-25)47-6)15-27-33-36(4,5)39(33,50-23(3)40)35(22(2)38(27,30)46)49-32(43)17-24-10-8-7-9-11-24/h7-16,22,27,30,33,35,41,45-46H,17-20H2,1-6H3/t22-,27+,30-,33-,35-,37-,38-,39-/m1/s1
• InChIKey: OGRGWTXWAZBJKF-JXWJAAHMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(1S,2S,6R,10S,11R,13S,14R,15R)-13-(acetyloxy)-1,6-dihydroxy-4,12,12,15-tetramethyl-5-oxo-14-[(2-phenylacetyl)oxy]tetracyclo[8.5.0.0^2,^6.0^1^1,^1^3]pentadeca-3,8-dien-8-yl]methyl 2-(4-hydroxy-3-methoxyphenyl)acetate
• IUPAC Traditional name: [(1S,2S,6R,10S,11R,13S,14R,15R)-13-(acetyloxy)-1,6-dihydroxy-4,12,12,15-tetramethyl-5-oxo-14-[(2-phenylacetyl)oxy]tetracyclo[8.5.0.0^2,^6.0^1^1,^1^3]pentadeca-3,8-dien-8-yl]methyl 2-(4-hydroxy-3-methoxyphenyl)acetate
• Synonyms: PPAHV; Phorbol 12-phenylacetate 13-acetate 20-homovanillate

Database IDs

• CAS Number: 175796-50-6
• MDL Number: MFCD06411584
• PubChem SID: 24898345; 162227762
• PubChem CID: 3035862

CALCULATED PROPERTIES

• Acid pKa: 9.9353485
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): 3.7499206
• LogD (pH = 7.4): 3.7486806
• Log P: 3.7499366
• Molar Refractivity: 181.1198 cm^3
• Polarizability: 71.19982 Å^3
• Polar Surface Area: 165.89 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: soluble; H2O: insoluble
• Apperance: white solid

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

DETAILS

Sigma Aldrich - P266

Biochem/physiol Actions
Vanilloid receptor agonist.
Legal Information
Sold in France, Germany, Great Britain and Switzerland under license, restricted to research use only, from Procyon Pharmaceuticals, Inc.