(1S,2R,10S,11S,14S,15S)-14-(2H3)acetyl-2,15-dimethyl(4,4,6,8,8,14-2H6)tetracyclo[8.7.0.02,7.011,15]heptadec-6-en-5-one

• ChemBase ID: 135576
• Molecular Formular: C21H30O2
• Molecular Mass: 314.4617
• Monoisotopic Mass: 314.2245802
• SMILES: C1=C2[C@](CCC1=O)([C@H]1CC[C@]3([C@H]([C@@H]1CC2)CC[C@@H]3C(=O)C)C)C
• Canonical SMILES: O=C1CC[C@]2(C(=C1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2C(=O)C)C)C
• InChI: InChI=1S/C21H30O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h12,16-19H,4-11H2,1-3H3/t16-,17+,18-,19-,20-,21+/m0/s1
• InChIKey: RJKFOVLPORLFTN-LEKSSAKUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10S,11S,14S,15S)-14-(^2H₃)acetyl-2,15-dimethyl(4,4,6,8,8,14-^2H₆)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one
• IUPAC Traditional name: (1S,2R,10S,11S,14S,15S)-14-(^2H₃)acetyl-2,15-dimethyl(4,4,6,8,8,14-^2H₆)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one
• Synonyms: Progesterone-2,2,4,6,6,17α,21,21,21-d9; Pregn-4-ene-3,20-dione-d9; Δ4-Pregnene-3,20-dione-d9; Agolutin-d9; Bio-luton-d9; CIDR-d9; Corlutin-d9; Corlutina-d9; Corluvite-d9; Gestone-d9; Progestan-d9; Progestasert-d9; Progestogel-d9; Progesterone-2,2,4,6,6,17a,21,21,21-d9; Progesterone-d9; 孕酮-2,2,4,6,6,17α,21,21,21-d9

Database IDs

• MDL Number: MFCD01317491
• PubChem SID: 162229850
• PubChem CID: 71309321

CALCULATED PROPERTIES

• Acid pKa: 18.916313
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 4.1486044
• LogD (pH = 7.4): 4.1486044
• Log P: 4.1486044
• Molar Refractivity: 92.7053 cm^3
• Polarizability: 36.39888 Å^3
• Polar Surface Area: 34.14 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Chloroform
• Apperance: White to Off-White Solid
• Melting Point: 120-122°C; 128-132 °C
• Mass Shift: M+9

Safety Information

• Storage Condition: -20°C Freezer
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 40
• Safety Statements: 36/37
• GHS Pictograms: GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H351
• GHS Precautionary statements: P281

Product Information

• Purity: 98% (CP)
• Isotopic Purity: 98 atom % D
• Empirical Formula (Hill Notation): C21D9H21O2

DETAILS

Sigma Aldrich - 672904

Packaging
This product may be available from bulk stock and can be packaged on demand. For information on pricing, availability and packaging, please contact Stable Isotopes Customer Service.

Toronto Research Chemicals - P755902

Sterid hormone produced by the corpus luteum. Induces maturation and secretory activity of the uterine endothelium; suppresses ovulation. Progesterone is implicated in the etiology of breast cancer.

REFERENCES

• Anderson, E., et al.: Breast Cancer Res., 4, 197 (2002)
• Lanari, C., et al.: Breast Cancer Res., 4, 240 (2002)
• Albrecht, E.D., et al.: Front. Biosci., 8, 416 (2002)
• Qiu, M., et al.: J. Steroid Biochem. Mol. Biol., 85, 147 (2002)