(1S,2R,10S,11S,13R,14R,15S)-14-acetyl-13-hydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-6-en-5-one

• ChemBase ID: 138848
• Molecular Formular: C21H30O3
• Molecular Mass: 330.4611
• Monoisotopic Mass: 330.21949482
• SMILES: CC(=O)[C@H]1[C@@H](C[C@@H]2[C@@]1(CC[C@H]1[C@H]2CCC2=CC(=O)CC[C@]12C)C)O
• Canonical SMILES: O=C1CC[C@]2(C(=C1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1C[C@H]([C@@H]2C(=O)C)O)C)C
• InChI: InChI=1S/C21H30O3/c1-12(22)19-18(24)11-17-15-5-4-13-10-14(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: LOVNYFVWYTXDRE-RMWFXKKMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10S,11S,13R,14R,15S)-14-acetyl-13-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one
• IUPAC Traditional name: 16α-hydroxyprogesterone
• Synonyms: 16α-Hydroxy-4-pregnene-3,20-dione; 16α-Hydroxypregn-4-ene-3,20-dione; 4-Pregnen-16α-ol-3,20-dione; 16α-Hydroxyprogesterone; 16α-Hydroxy-Δ4-pregnene-3,20-dione; 16α-Hydroxyprogesterone; (16α)-16-Hydroxypregn-4-ene-3,20-dione; NSC 523249; NSC 53910; 16α-Hydroxy Progesterone; 16α-羟基-4-孕烯-3,20-二酮; 16α-羟基孕-4-烯-3,20-二酮; 4-孕烯-16α-醇-3,20-二酮; 16α-羟基孕酮

Database IDs

• CAS Number: 438-07-3
• MDL Number: MFCD00010484
• PubChem SID: 162233099
• PubChem CID: 243761

CALCULATED PROPERTIES

• Acid pKa: 14.750564
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 2.9177933
• LogD (pH = 7.4): 2.9177933
• Log P: 2.9177933
• Molar Refractivity: 94.2208 cm^3
• Polarizability: 37.013763 Å^3
• Polar Surface Area: 54.37 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: 97%
• Empirical Formula (Hill Notation): C21H30O3

DETAILS

Toronto Research Chemicals - H952430

16α-Hydroxyprrogesterone is a hydroxylated metabolite of Progesterone (P755900). 16α-Hydroxyprogesterone binds to human progesterone receptors hPR-A and hPR-B and act as an agonist for both receptors.

REFERENCES

• Ikonen, M. et al.: Nature, 212, 716 (1966)
• Storbeck, K.-H. et al.: Mol. Cell. Endocrinol., 336, 92 (1966)