3-[(3S,3aS,5aS,6R,9aS,9bS)-3-hydroxy-3a,6-dimethyl-7-oxo-dodecahydro-1H-cyclopenta[a]naphthalen-6-yl]propanoic acid

• ChemBase编号: 175712
• 分子式: C18H28O4
• 平均质量: 308.41252
• 单一同位素质量: 308.19875938
• SMILES: [C@@]12([C@@H](CC[C@@H]1O)[C@H]1[C@H](CC2)[C@](C(=O)CC1)(CCC(=O)O)C)C
• Canonical SMILES: OC(=O)CC[C@@]1(C)C(=O)CC[C@@H]2[C@@H]1CC[C@]1([C@H]2CC[C@@H]1O)C
• InChI: InChI=1S/C18H28O4/c1-17-9-7-13-11(12(17)4-6-15(17)20)3-5-14(19)18(13,2)10-8-16(21)22/h11-13,15,20H,3-10H2,1-2H3,(H,21,22)/t11-,12-,13-,15-,17-,18+/m0/s1
• InChIKey: COGRAKQBTBRYQC-HHJOSPGFSA-N

名称和登记号

名称

• IUPAC标准名: 3-[(3S,3aS,5aS,6R,9aS,9bS)-3-hydroxy-3a,6-dimethyl-7-oxo-dodecahydro-1H-cyclopenta[a]naphthalen-6-yl]propanoic acid
• IUPAC传统名: 3-[(3S,3aS,5aS,6R,9aS,9bS)-3-hydroxy-3a,6-dimethyl-7-oxo-decahydrocyclopenta[a]naphthalen-6-yl]propanoic acid
• 别名: (3S,3aS,5aS,6R,9aS,9bS)-Dodecahydro-3-hydroxy-3a,6-dimethyl-7-oxo-1H-benz[e]indene-6-propanoic Acid; 17β-Hydroxy-5-oxo-A-nor-3,5-secoandrostan-3-oic Acid; [3S-(3α,3aα,5aβ,6β,9aα,9bβ)]-Dodecahydro-3-hydroxy-3a,6-dimethyl-7-oxo-1H-benz[e]indene-6-propanoic Acid; 3,5-Seco-A-norandrostan-17β-ol-5-on-3-oic Acid; 4-Nor-3,5-seco-5-oxo-17β-hydroxyandrostan-3-oic Acid

登记号

• CAS号: 1759-35-9
• PubChem SID: 164231622
• PubChem CID: 15819090

理论计算性质

• Acid pKa: 4.5958886
• 质子受体: 4
• 质子供体: 2
• LogD (pH = 5.5): 1.8255329
• LogD (pH = 7.4): 0.049756456
• Log P: 2.7796571
• 摩尔折射率: 82.5739 cm^3
• 极化性: 32.920235 Å^3
• 极化表面积: 74.6 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

详细说明

Toronto Research Chemicals - N825910

4-Nor-3,5-seco-5-oxo-17β-hydroxyandrostan-3-oic Acid is an open A-ring steroid that showed inhibitory activity on hormone binding by an extract from Nippostrongylus brasiliensis (Nematoda). It is used in the preparation on heterocyclic steroids.

参考文献

• Majundar, T.K. et al.: Comp. Biochem. Physiol. Biochem. Mol. Biol., 88B, 81 (1987)
• Borthakur, M. et al.: Steroids, 73, 637 (1987)