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

• ChemBase ID: 175711
• Molecular Formular: C18H26O4
• Molecular Mass: 306.39664
• Monoisotopic Mass: 306.18310931
• SMILES: [C@@]12([C@@H](CCC1=O)[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]2CCC1=O)C
• InChI: InChI=1S/C18H26O4/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/h11-13H,3-10H2,1-2H3,(H,21,22)/t11-,12-,13-,17-,18+/m0/s1
• InChIKey: YUQOAWJBIXWZRK-HHDFAXHISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[(3aS,5aS,6R,9aR,9bS)-3a,6-dimethyl-3,7-dioxo-dodecahydro-1H-cyclopenta[a]naphthalen-6-yl]propanoic acid
• IUPAC Traditional name: 3-[(3aS,5aS,6R,9aR,9bS)-3a,6-dimethyl-3,7-dioxo-octahydro-1H-cyclopenta[a]naphthalen-6-yl]propanoic acid
• Synonyms: (3aS,5aS,6R,9aR,9bS)-Dodecahydro-3a,6-dimethyl-3,7-dioxo-1H-benz[e]indene-6-propanoic Acid; 5,17-Dioxo-3,5-seco-A-norandrostan-3-oic Acid; [3aS-(3aα,5aβ,6β,9aα,9bβ)]-Dodecahydro-3a,6-dimethyl-3,7-dioxo-1H-benz[e]indene-6-propanoic Acid; 4-Nor-3,5-seco-5,17-dioxoandrostan-3-oic Acid

Database IDs

• CAS Number: 6857-88-1
• PubChem SID: 164231621
• PubChem CID: 13870404

CALCULATED PROPERTIES

• Acid pKa: 4.55878
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 2.3560066
• LogD (pH = 7.4): 0.582326
• Log P: 3.3431847
• Molar Refractivity: 81.7516 cm^3
• Polarizability: 32.377407 Å^3
• Polar Surface Area: 71.44 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 57-62°C

Safety Information

• Storage Condition: -20°C Freezer, Under inert atmosphere

DETAILS

Toronto Research Chemicals - N825900

4-Nor-3,5-seco-5,17-dioxoandrostan-3-oic Acid is an open A-ring steroid. It is used in the preparation on heterocyclic steroids such as Finesteride.

REFERENCES

• Nguyen, H. et al.: Tap Chi Duoc Hoc, 49, 31 (2009)
• Borthakur, M. et al.: Steroids, 73, 637 (2009)