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

• ChemBase ID: 153265
• Molecular Formular: C30H36O7
• Molecular Mass: 508.60264
• Monoisotopic Mass: 508.24610349
• SMILES: C[C@@H]1C[C@@]2([C@@H](C2(C)C)[C@H]2[C@]1([C@@H]1C=C(C(=O)[C@]1(CC(=C2)COC(=O)C)O)C)O)OC(=O)Cc1ccccc1
• Canonical SMILES: O=C(O[C@@]12C[C@@H](C)[C@]3([C@H]([C@@H]1C2(C)C)C=C(COC(=O)C)C[C@]1([C@H]3C=C(C1=O)C)O)O)Cc1ccccc1
• InChI: InChI=1S/C30H36O7/c1-17-11-23-28(34,26(17)33)15-21(16-36-19(3)31)12-22-25-27(4,5)29(25,14-18(2)30(22,23)35)37-24(32)13-20-9-7-6-8-10-20/h6-12,18,22-23,25,34-35H,13-16H2,1-5H3/t18-,22+,23-,25-,28-,29+,30-/m1/s1
• InChIKey: MEDVHSNRBPAIPU-XMOZQXTISA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 54662-30-5
• PubChem SID: 162247404
• PubChem CID: 3034821

CALCULATED PROPERTIES

• Acid pKa: 12.575741
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 2.9690547
• LogD (pH = 7.4): 2.9690518
• Log P: 2.9690547
• Molar Refractivity: 137.5396 cm^3
• Polarizability: 53.990505 Å^3
• Polar Surface Area: 110.13 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: ≥5 mg/mL
• Apperance: white to tan powder

Safety Information

• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C30H36O7

DETAILS

Sigma Aldrich - D7821

Biochem/physiol Actions
Selective activator of PKC beta
dPPA is a phorbol ester that selectively activates the beta isotype of PKC. It is approximately 100-fold more potent for PKC-beta than the alpha, gamma or delta isotypes. PKC family members each have specific functions, but PKC-beta and delta appear to share similar expression profiles, and both are involved in regulating apoptosis and B cell activation, thus dPPA is a useful tool in determining PKCbeta specific signaling events.