(1S,2R,10S,11S,14S,15S,17R)-14-acetyl-17-hydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-6-en-5-one

• ChemBase ID: 102178
• Molecular Formular: C21H30O3
• Molecular Mass: 330.4611
• Monoisotopic Mass: 330.21949482
• SMILES: O=C1C=C2[C@]([C@H]3[C@H](O)C[C@@]4([C@@H](C(=O)C)CC[C@H]4[C@@H]3CC2)C)(C)CC1
• Canonical SMILES: O=C1CC[C@]2(C(=C1)CC[C@@H]1[C@@H]2[C@H](O)C[C@]2([C@H]1CC[C@@H]2C(=O)C)C)C
• InChI: InChI=1S/C21H30O3/c1-12(22)16-6-7-17-15-5-4-13-10-14(23)8-9-20(13,2)19(15)18(24)11-21(16,17)3/h10,15-19,24H,4-9,11H2,1-3H3/t15-,16+,17-,18+,19+,20-,21+/m0/s1
• InChIKey: BFZHCUBIASXHPK-QJSKAATBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10S,11S,14S,15S,17R)-14-acetyl-17-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one; (1S,2R,10S,11S,14S,15S,17R)-14-acetyl-17-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one
• IUPAC Traditional name: 11α-hydroxyprogesterone
• Synonyms: 11-α-HYDROXYPROGESTERONE; (8S,9S,10R,11R,13S,14S,17S)-17-acetyl-11-hydroxy-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3(2H)-one; (11α)-11-Hydroxypregn-4-ene-3,20-dione; 11-Hydroxyprogesterone; 4-Pregnene-11α-ol-3,20-dione; DG 322B; NSC 3350; Pregn-4-en-11α-ol-3,20-dione; U 0384; 11α-Hydroxy Progesterone; δ₄-Pregnen-11α-ol-3,20-dione; 11α-Hydroxy-4-pregnene-3,20-dione; 11α-HYDROXYPROGESTERONE; 11α-Hydroxypregn-4-ene-3,20-dione; 4-Pregnen-11α-ol-3,20-dione; (+)-11α-Hydroxyprogesterone; 11α-羟基孕-4-烯-3,20-二酮; 4-孕烯-11α-醇-3,20-二酮; (+)-11α-孕酮

Database IDs

• CAS Number: 80-75-1
• EC Number: 201-306-9
• MDL Number: MFCD00003652
• PubChem SID: 162088685
• PubChem CID: 92730

CALCULATED PROPERTIES

• Acid pKa: 18.875326
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 2.83984
• 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

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White Solid
• Melting Point: 165-166 °C(lit.); 166-168°C
• Optical Rotation: [α]22/D +179.5°, c = 1 in chloroform

Safety Information

• Storage Condition: Refrigerator; Room Temperature (15-30°C)
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: 95%
• Empirical Formula (Hill Notation): C21H30O3

DETAILS

MP Biomedicals - 02100482

Crystalline

MP Biomedicals - 05210765

MP Biomedicals Rare Chemical collection

Toronto Research Chemicals - H952335

Progesterone (P755900) metabolite.

REFERENCES

• Christy H., et al.: J. Steroid Biochem., Mol., Biol., 116, 171 (2009)
• Peristera, O., et al.: Toxicol., Lett., 189, 219 (2009)
• Mori, T., et al.: Toxicol., Lett., 186, 123 (2009)