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

• ChemBase ID: 175712
• Molecular Formular: C18H28O4
• Molecular Mass: 308.41252
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[(3S,3aS,5aS,6R,9aS,9bS)-3-hydroxy-3a,6-dimethyl-7-oxo-dodecahydro-1H-cyclopenta[a]naphthalen-6-yl]propanoic acid
• IUPAC Traditional name: 3-[(3S,3aS,5aS,6R,9aS,9bS)-3-hydroxy-3a,6-dimethyl-7-oxo-decahydrocyclopenta[a]naphthalen-6-yl]propanoic acid
• Synonyms: (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

Database IDs

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

CALCULATED PROPERTIES

• Acid pKa: 4.5958886
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 1.8255329
• LogD (pH = 7.4): 0.049756456
• Log P: 2.7796571
• Molar Refractivity: 82.5739 cm^3
• Polarizability: 32.920235 Å^3
• Polar Surface Area: 74.6 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

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.

REFERENCES

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