(1S,2S,6R,10S,11R,13S,14R,15R)-14-(decanoyloxy)-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 decanoate

• ChemBase ID: 133031
• Molecular Formular: C40H64O8
• Molecular Mass: 672.93136
• Monoisotopic Mass: 672.46011901
• SMILES: CCCCCCCCCC(=O)O[C@@H]1[C@H]([C@]2([C@@H](C=C(C[C@]3([C@H]2C=C(C3=O)C)O)CO)[C@@H]2[C@@]1(C2(C)C)OC(=O)CCCCCCCCC)O)C
• Canonical SMILES: CCCCCCCCCC(=O)O[C@@H]1[C@@H](C)[C@@]2(O)[C@H]([C@@H]3[C@]1(OC(=O)CCCCCCCCC)C3(C)C)C=C(C[C@]1([C@H]2C=C(C1=O)C)O)CO
• InChI: InChI=1S/C40H64O8/c1-7-9-11-13-15-17-19-21-32(42)47-36-28(4)39(46)30(24-29(26-41)25-38(45)31(39)23-27(3)35(38)44)34-37(5,6)40(34,36)48-33(43)22-20-18-16-14-12-10-8-2/h23-24,28,30-31,34,36,41,45-46H,7-22,25-26H2,1-6H3/t28-,30+,31-,34?,36-,38-,39-,40-/m1/s1
• InChIKey: DGOSGFYDFDYMCW-WCCOWUOISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,6R,10S,11R,13S,14R,15R)-14-(decanoyloxy)-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 decanoate
• IUPAC Traditional name: (1S,2S,6R,10S,11R,13S,14R,15R)-14-(decanoyloxy)-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 decanoate
• Synonyms: PDD; Phorbol 12,13-dicaprinate; Phorbol 12,13-didecanoate

Database IDs

• CAS Number: 24928-17-4
• MDL Number: MFCD00065449
• Beilstein Number: 6036113
• PubChem SID: 162227308; 24899003
• PubChem CID: 71308620

CALCULATED PROPERTIES

• Acid pKa: 12.570371
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 7.726401
• LogD (pH = 7.4): 7.726398
• Log P: 7.726401
• Molar Refractivity: 187.7482 cm^3
• Polarizability: 74.46961 Å^3
• Polar Surface Area: 130.36 Å^2
• Rotatable Bonds: 21
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: soluble; ethanol: soluble; methanol: soluble
• Apperance: white solid

Safety Information

• RTECS: GZ0653000
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

DETAILS

Sigma Aldrich - P9018

Biochem/physiol Actions
Strong NO promoter; potent activator of protein kinase C; promotes iNOS expression in cultured hepatocytes.
Caution
Photosensitive
General description
More potent than phorbol myristate acetate as an inflammatory agent, but weaker as a tumor promoting agent
Reconstitution
A stock solution cannot be made in aqueous media; dissolve in a water-miscible organic solvent before dilution to working concentrations in aqueous media.