(1S,2R,10R,11S,14R,15S)-14-acetyl-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

• ChemBase ID: 103362
• Molecular Formular: C21H30O3
• Molecular Mass: 330.4611
• Monoisotopic Mass: 330.21949482
• SMILES: O=C1C=C2[C@]([C@H]3CC[C@@]4([C@@](O)(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]2CC[C@]2([C@H]1CC[C@]2(O)C(=O)C)C)C
• InChI: InChI=1S/C21H30O3/c1-13(22)21(24)11-8-18-16-5-4-14-12-15(23)6-9-19(14,2)17(16)7-10-20(18,21)3/h12,16-18,24H,4-11H2,1-3H3/t16-,17+,18+,19+,20+,21+/m1/s1
• InChIKey: DBPWSSGDRRHUNT-CEGNMAFCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10R,11S,14R,15S)-14-acetyl-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one; (1S,2R,10R,11S,14R,15S)-14-acetyl-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one
• IUPAC Traditional name: hydroxyprogesterone
• Synonyms: 17-Hydroxypregn-4-ene-3,20-dione; 17-Hydroxyprogesterone; 17α-Hydroxy-P4; 17α-Hydroxylutin; 17α-Hydroxypregn-4-ene-3,20-dione; 17α-Hydroxyprogesterone; Gestageno; Gestageno Gador; Hydroxyprogesterone; NSC 15468; Pregn-4-en-17α-ol-3,20-dione; Prodix; Prodox; U 3096; Δ4-Pregnen-17α-ol-3,20-dione; 17α-Hydroxy Progesterone; 17α-Hydroxyprogesterone; 17-Hydroxyprogesterone; 17α-Hydroxy-4-pregnene-3,20-dione; 4-Pregnen-17α-ol-3,20-dione; 17-α-Hydroxypregn-4-ene-3,20-dione; 4-Pregnen-17α-ol-3,20-dione; 17α-HYDROXYPROGESTERONE; (8R,9S,10R,13S,14S,17R)-17-acetyl-17-hydroxy-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3(2H)-one; 17A-hydroxyprogesterone; Hydroxyprogesterone; 17α-羟基孕甾-4-烯-3,20-二酮; 17α-羟基黄体酮; 17α-羟基孕酮

Database IDs

• CAS Number: 68-96-2
• EC Number: 200-699-4
• MDL Number: MFCD00003659
• Beilstein Number: 3218109
• PubChem SID: 24870056; 24278469; 162090857
• PubChem CID: 6238
• CHEBI ID: 17252
• ATC CODE: G03DA03
• CHEMBL: 1062
• Chemspider ID: 6002
• Unique Ingredient Identifier: 21807M87J2
• Wikipedia Title: 17-Hydroxyprogesterone

CALCULATED PROPERTIES

• Acid pKa: 12.699646
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 3.4011793
• LogD (pH = 7.4): 3.4011772
• Log P: 3.4011793
• Molar Refractivity: 94.1053 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; Dichloromethane
• Apperance: White Solid
• Melting Point: 219.5°C (427.1°F); 222-223°C; 222-224°C

Safety Information

• Storage Condition: -20°C Freezer; Room Temperature (15-30°C)
• RTECS: TU5060000
• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 61
• Safety Statements: 53-22-36/37/39-45
• GHS Pictograms: GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H360
• GHS Precautionary statements: P201-P308 + P313
• Personal Protective Equipment: Eyeshields, Gloves, type P2 (EN 143) respirator cartridges

Pharmacology Properties

• Admin Routes: Intramuscular
• Half Life: 10 days (17-OHPC)
• Metabolism: Liver
• Legal Status: Rx-only (US)
• Pregnancy Category: B; B (US)
• US Licence: Hydroxyprogesterone
• Gene Information: human ... PGR(5241), SERPINA6(866)rat ... Ar(24208); human ... SERPINA6(866)rat ... Ar(24208)

Product Information

• Purity: ≥95%; 95+%; 98%
• Grade: VETRANAL™, analytical standard
• Empirical Formula (Hill Notation): C21H30O3

DETAILS

MP Biomedicals - 02151498

Crystalline

Sigma Aldrich - H5752

Biochem/physiol Actions
Metabolite of progesterone.

Sigma Aldrich - 46337

Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

Toronto Research Chemicals - H952330

17α-Hydroxy Progesterone is a metabolite of Progesterone. It was isolated from adrenal glands.

REFERENCES

• Pfiffner, N., et al.: J. Biol. Chem., 132, 459 (1940)
• Florey, K., et al.: Anal. Profiles Drug Subs.,4, 209 (1940)