(1S,2R,10R,11S,12R,14S,15S)-14-acetyl-12-hydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-6-en-5-one

• ChemBase ID: 171173
• Molecular Formular: C21H30O3
• Molecular Mass: 330.4611
• Monoisotopic Mass: 330.21949482
• SMILES: C1C(=O)C=C2[C@](C1)([C@@H]1[C@@H](CC2)[C@H]2[C@](CC1)([C@H](C[C@H]2O)C(=O)C)C)C
• Canonical SMILES: O=C1CC[C@]2(C(=C1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1[C@H](O)C[C@@H]2C(=O)C)C)C
• InChI: InChI=1S/C21H30O3/c1-12(22)17-11-18(24)19-15-5-4-13-10-14(23)6-8-20(13,2)16(15)7-9-21(17,19)3/h10,15-19,24H,4-9,11H2,1-3H3/t15-,16+,17-,18-,19-,20+,21-/m1/s1
• InChIKey: LEWIUXKKQXGQRR-XCEZYFHXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10R,11S,12R,14S,15S)-14-acetyl-12-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one
• IUPAC Traditional name: 15β-hydroxyprogesterone
• Synonyms: 15β-Hydroxy-4-pregnene-3,20-dione; (15β)-15-Hydroxypregn-4-ene-3,20-dione; 15β-Hydroxyprogesterone; 15β-Hydroxy Progesterone

Database IDs

• CAS Number: 600-72-6
• PubChem SID: 164227083
• PubChem CID: 23239834

CALCULATED PROPERTIES

• Acid pKa: 14.896733
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 2.8398397
• LogD (pH = 7.4): 2.8398397
• Log P: 2.8398397
• Molar Refractivity: 94.2978 cm^3
• Polarizability: 37.013763 Å^3
• Polar Surface Area: 54.37 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H952425

15β-Hydroxyprogesterone is a hydroxylated metabolite of Progesterone (P755900).

REFERENCES

• Gustafsson, J.A. et al.: Eur. J. Biochem., 15, 525 (1970)
• Kang, M.-J. et al.: Rap, Comm. Mass Spec., 18, 2795 (1970)