2-hydroxy-1-[(1S,2S,5S,7S,10R,11S,14S,15S)-5-hydroxy-2,15-dimethyl(4,4,6,6-2H4)tetracyclo[8.7.0.02,7.011,15]heptadecan-14-yl]ethan-1-one

• ChemBase ID: 167869
• Molecular Formular: C21H34O3
• Molecular Mass: 334.49286
• Monoisotopic Mass: 334.25079495
• SMILES: C1C[C@@H](C[C@H]2[C@]1([C@@H]1[C@@H](CC2)[C@H]2[C@](CC1)([C@H](CC2)C(=O)CO)C)C)O
• Canonical SMILES: OCC(=O)[C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CC[C@@H]2[C@]1(C)CC[C@@H](C2)O
• InChI: InChI=1S/C21H34O3/c1-20-9-7-14(23)11-13(20)3-4-15-16-5-6-18(19(24)12-22)21(16,2)10-8-17(15)20/h13-18,22-23H,3-12H2,1-2H3/t13-,14-,15-,16-,17-,18+,20-,21-/m0/s1
• InChIKey: CYKYBWRSLLXBOW-VTBMCCKRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-hydroxy-1-[(1S,2S,5S,7S,10R,11S,14S,15S)-5-hydroxy-2,15-dimethyl(4,4,6,6-^2H₄)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]ethan-1-one
• IUPAC Traditional name: 2-hydroxy-1-[(1S,2S,5S,7S,10R,11S,14S,15S)-5-hydroxy-2,15-dimethyl(4,4,6,6-^2H₄)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]ethanone
• Synonyms: (3β,5α)-3,21-Dihydroxy-pregnan-20-one-d4; 3β,5α-Tetrahydrodeoxycorticosterone-d4; 3β,21-Dihydroxy-5α-pregnan-20-one-d4

Database IDs

• PubChem SID: 162262002
• PubChem CID: 71316271

CALCULATED PROPERTIES

• Acid pKa: 13.864726
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 3.16969
• LogD (pH = 7.4): 3.1696897
• Log P: 3.16969
• Molar Refractivity: 94.6089 cm^3
• Polarizability: 37.801956 Å^3
• Polar Surface Area: 57.53 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D454537

A labelled metabolite of Progesterone. A new corticosteroid, isolated from the urine of women in the 3rd trimester of pregnancy.

REFERENCES

• Pasqualini, J. R., et al.: J. Clin. Endocrinol. Metab., 38, 298 (1974)
• De Kloet, E., et al.: Eur. J. Pharmacol., 405, 187 (1974)
• Huang, X., et al.: J. Biol. Chem., 275, 29452 (1974)
• Smith, S., et al.: Steroids, 67, 519 (1974)