(1R,2S,6R,10S,11R,13S,15R)-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 acetate

• ChemBase ID: 129142
• Molecular Formular: C22H30O6
• Molecular Mass: 390.47
• Monoisotopic Mass: 390.20423868
• SMILES: O=C1C(=C[C@H]2[C@]3(O)[C@@H](C=C(CO)C[C@]12O)[C@H]1[C@@](OC(=O)C)(C[C@H]3C)C1(C)C)C
• Canonical SMILES: OCC1=C[C@H]2[C@H]3[C@@](C3(C)C)(OC(=O)C)C[C@H]([C@@]2([C@H]2[C@@](C1)(O)C(=O)C(=C2)C)O)C
• InChI: InChI=1S/C22H30O6/c1-11-6-16-20(26,18(11)25)9-14(10-23)7-15-17-19(4,5)21(17,28-13(3)24)8-12(2)22(15,16)27/h6-7,12,15-17,23,26-27H,8-10H2,1-5H3/t12-,15+,16-,17-,20-,21+,22-/m1/s1
• InChIKey: BOJKFRKNLSCGHY-HXGSDTCMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,6R,10S,11R,13S,15R)-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 acetate
• IUPAC Traditional name: prostratin
• Synonyms: 12-Deoxyphorbol-13-acetate; Prostratin; CCRIS 6292; NSC 623310; Prostratin

Database IDs

• CAS Number: 60857-08-1
• MDL Number: MFCD00674138
• PubChem SID: 162223441
• PubChem CID: 454217
• CHEMBL: 170518
• Chemspider ID: 399975
• Wikipedia Title: Prostratin

CALCULATED PROPERTIES

• Acid pKa: 12.574634
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 0.6935895
• LogD (pH = 7.4): 0.69358665
• Log P: 0.69358957
• Molar Refractivity: 103.6662 cm^3
• Polarizability: 40.592663 Å^3
• Polar Surface Area: 104.06 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: soluble30 mg/mL
• Apperance: white powder

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: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C22H30O6

DETAILS

Sigma Aldrich - P0077

Biochem/physiol Actions
Prostratin, an unusual non-tumorigenic phorbol ester, is an activator of protein kinase C (PKC) and also an activator of nuclear factor KB (NF-KB) mediated through activation of the IKKs (IKB kinases). Prostratin exhibits potent in vitro activity by inducing HIV expression in latently infected cell lines and primary cells, thus antagonizing HIV latency. Activation of PKC and NF-kB has been proposed as the mechanism of action. Prostratin also inhibits HIV entry into target cells by down-regulating CD4 and CXCR4 receptors.