(1S,2R,5R,10R,11S,14S,15S)-15-methyltetracyclo[8.7.0.02,7.011,15]heptadec-6-ene-5,14-diol

• ChemBase ID: 153940
• Molecular Formular: C18H28O2
• Molecular Mass: 276.41372
• Monoisotopic Mass: 276.20893014
• SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)CCC1=C[C@@H](CC[C@H]31)O
• Canonical SMILES: O[C@@H]1CC[C@H]2C(=C1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2O)C
• InChI: InChI=1S/C18H28O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h10,12-17,19-20H,2-9H2,1H3/t12-,13+,14-,15-,16+,17+,18+/m1/s1
• InChIKey: CMXKUJNZWYTFJN-AXSMETJDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,5R,10R,11S,14S,15S)-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-ene-5,14-diol
• IUPAC Traditional name: (1S,2R,5R,10R,11S,14S,15S)-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-ene-5,14-diol
• Synonyms: 4-Estren-3α,17β-diol; Estren

Database IDs

• CAS Number: 35950-87-9
• MDL Number: MFCD00271605
• PubChem SID: 162248079
• PubChem CID: 9921701

CALCULATED PROPERTIES

• Acid pKa: 17.524961
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 2.6540375
• LogD (pH = 7.4): 2.6540377
• Log P: 2.6540377
• Molar Refractivity: 80.8521 cm^3
• Polarizability: 31.964787 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 203-207 °C
• Optical Rotation: [α]/D +124±5°, c = 1 in methanol

Safety Information

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

Product Information

• Purity: ≥98.0% (TLC)
• Empirical Formula (Hill Notation): C18H28O2

DETAILS

Sigma Aldrich - 43620

Application
Therapeutic alternative to hormone replacement for osteoporosis of bone mass in both women and men.1,2 Estren increased neuronal viability to a similar extent as that observed with 17α- and 17β-estradiol, by a pathway mediated by protein kinase C.3
Biochem/physiol Actions
Estren is a synthetic steroid that acts via the androgen receptor. It has been shown to directly activate transcription and increases the proliferation of MCF-7 human breast cancer cells in vitro.4