(1S,2S,7S,10R,11S,14S,15S)-14-acetyl-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadecan-5-one

• ChemBase ID: 107671
• Molecular Formular: C21H32O2
• Molecular Mass: 316.47758
• Monoisotopic Mass: 316.24023026
• SMILES: O=C1C[C@@H]2CC[C@@H]3[C@H](CC[C@]4(C)[C@@H](C(=O)C)CC[C@@H]34)[C@@]2(C)CC1
• Canonical SMILES: O=C1CC[C@]2([C@H](C1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2C(=O)C)C)C
• InChI: InChI=1S/C21H32O2/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/h14,16-19H,4-12H2,1-3H3/t14-,16-,17+,18-,19-,20-,21+/m0/s1
• InChIKey: XMRPGKVKISIQBV-BJMCWZGWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,7S,10R,11S,14S,15S)-14-acetyl-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-5-one; (1S,2S,7S,10R,11S,14S,15S)-14-acetyl-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-one
• IUPAC Traditional name: 5a-pregnane-3,20-dione
• Synonyms: 5α-Dihydroprogesterone; ALLOPREGNAN-3,20-DIONE; 5α-Dihydroprogesterone; Allopregnane-3,20-dione; 5α-Pregnane-3,20-dione (allo)

Database IDs

• CAS Number: 566-65-4
• EC Number: 209-297-3
• MDL Number: MFCD00067132
• PubChem SID: 162094842; 24898872
• PubChem CID: 92810; 24779611
• Wikipedia Title: 5α-Dihydroprogesterone

CALCULATED PROPERTIES

• Acid pKa: 19.343395
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 4.194439
• LogD (pH = 7.4): 4.194439
• Log P: 4.194439
• Molar Refractivity: 91.8786 cm^3
• Polarizability: 36.6383 Å^3
• Polar Surface Area: 34.14 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• RTECS: TU4157150
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

DETAILS

MP Biomedicals - 05204544

MP Biomedicals Rare Chemical collection

Sigma Aldrich - P7754

Biochem/physiol Actions
A high-level metabolite of progesterone in breast cancer tissue (but not normal breast tissue); promotes cell proliferation and detachment. Receptors appear only on the cell surface of MCF-7 breast cancer cells, not on nuclei where most other steroid receptors are located.1