(1S,6R,10S,11R,13S,14R)-13-(acetyloxy)-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.02,6.011,13]pentadeca-3,8-dien-14-yl tetradecanoate

• ChemBase ID: 125175
• Molecular Formular: C36H56O8
• Molecular Mass: 616.82504
• Monoisotopic Mass: 616.39751875
• SMILES: CCCCCCCCCCCCCC(=O)O[C@@H]1C(C)[C@]2(O)C3C=C(C)C(=O)[C@@]3(O)CC(=C[C@H]2[C@H]2[C@]1(OC(=O)C)C2(C)C)CO
• Canonical SMILES: CCCCCCCCCCCCCC(=O)O[C@@H]1C(C)[C@@]2(O)[C@H]([C@H]3[C@]1(OC(=O)C)C3(C)C)C=C(C[C@]1(C2C=C(C1=O)C)O)CO
• InChI: InChI=1S/C36H56O8/c1-7-8-9-10-11-12-13-14-15-16-17-18-29(39)43-32-24(3)35(42)27(30-33(5,6)36(30,32)44-25(4)38)20-26(22-37)21-34(41)28(35)19-23(2)31(34)40/h19-20,24,27-28,30,32,37,41-42H,7-18,21-22H2,1-6H3/t24?,27-,28?,30+,32+,34+,35+,36+/m0/s1
• InChIKey: PHEDXBVPIONUQT-AOWVHHMZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,6R,10S,11R,13S,14R)-13-(acetyloxy)-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-14-yl tetradecanoate
• IUPAC Traditional name: (1S,6R,10S,11R,13S,14R)-13-(acetyloxy)-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-14-yl tetradecanoate
• Synonyms: TPA; PMA; Phorbol myristate acetate; Tetradecanoylphorbol acetate.; 12-O-Tetradecanoylphorbol-13-acetate

Database IDs

• CAS Number: 16561-29-8
• PubChem SID: 162219525
• PubChem CID: 10475874; 22833501
• CHEMBL: 279115
• Chemspider ID: 17215855
• KEGG ID: C05151
• Wikipedia Title: 12-O-Tetradecanoylphorbol-13-acetate

CALCULATED PROPERTIES

• Acid pKa: 12.570371
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 5.692159
• LogD (pH = 7.4): 5.6921563
• Log P: 5.692159
• Molar Refractivity: 169.3183 cm^3
• Polarizability: 67.11437 Å^3
• Polar Surface Area: 130.36 Å^2
• Rotatable Bonds: 17
• Lipinski's Rule of Five: false