(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编号: 129142
• 分子式: C22H30O6
• 平均质量: 390.47
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: (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传统名: prostratin
• 别名: 12-Deoxyphorbol-13-acetate; Prostratin; CCRIS 6292; NSC 623310; Prostratin

登记号

• CAS号: 60857-08-1
• MDL号: MFCD00674138
• PubChem SID: 162223441
• PubChem CID: 454217
• CHEMBL: 170518
• Chemspider ID: 399975
• 维基百科标题: Prostratin

理论计算性质

• Acid pKa: 12.574634
• 质子受体: 5
• 质子供体: 3
• LogD (pH = 5.5): 0.6935895
• LogD (pH = 7.4): 0.69358665
• Log P: 0.69358957
• 摩尔折射率: 103.6662 cm^3
• 极化性: 40.592663 Å^3
• 极化表面积: 104.06 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: DMSO: soluble30 mg/mL
• 外观: white powder

安全信息

• 德国WGK号: 3
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 保存温度: -20°C

产品相关信息

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

详细说明

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.