(1S,2S,6S,10S,11R,13S,14R,15R)-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: 155345
• Molecular Formular: C36H56O8
• Molecular Mass: 616.82504
• Monoisotopic Mass: 616.39751875
• SMILES: CCCCCCCCCCCCCC(=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)C)O)C
• Canonical SMILES: CCCCCCCCCCCCCC(=O)O[C@@H]1[C@@H](C)[C@@]2(O)[C@H]([C@H]3[C@]1(OC(=O)C)C3(C)C)C=C(C[C@@]1([C@H]2C=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-/m1/s1
• InChIKey: PHEDXBVPIONUQT-AFPOFPRFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,6S,10S,11R,13S,14R,15R)-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,2S,6S,10S,11R,13S,14R,15R)-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: 4α-PMA; 4α-Phorbol 12-myristate 13-acetate

Database IDs

• CAS Number: 63597-44-4
• MDL Number: MFCD00153860
• Beilstein Number: 4775425
• PubChem SID: 24898203; 162249483
• PubChem CID: 122634

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

PROPERTIES

Physical Property

• Solubility: DMSO: soluble; ethanol: soluble; H2O: ~2 μM (Though having aqueous solubility, it is recommended that this compound first be dissolved in a water miscible organic solvent before dilution to working concentrations in aqueous media.)
• Apperance: white solid

Safety Information

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

Product Information

• Purity: ≥95% (TLC); ≥98.0% (HPLC)
• Empirical Formula (Hill Notation): C36H56O8

DETAILS

Sigma Aldrich - P148

Biochem/physiol Actions
Negative control for phorbol ester activation of protein kinase C.
Caution
Photosensitive
Packaging
Sealed glass ampule.

Sigma Aldrich - 79352

Biochem/physiol Actions
Negative control for phorbol ester activation of protein kinase C.