(15S)-14-hydroxy-14-(1-hydroxyethyl)-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-6-en-5-one

• ChemBase ID: 134321
• Molecular Formular: C21H32O3
• Molecular Mass: 332.47698
• Monoisotopic Mass: 332.23514488
• SMILES: CC(C1(CCC2[C@@]1(CCC1C2CCC2=CC(=O)CCC12C)C)O)O
• Canonical SMILES: O=C1CCC2(C(=C1)CCC1C2CC[C@]2(C1CCC2(O)C(O)C)C)C
• InChI: InChI=1S/C21H32O3/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/h12-13,16-18,22,24H,4-11H2,1-3H3/t13?,16?,17?,18?,19?,20-,21?/m0/s1
• InChIKey: MASCESDECGBIBB-SDBBSPJZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (15S)-14-hydroxy-14-(1-hydroxyethyl)-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one
• IUPAC Traditional name: (15S)-14-hydroxy-14-(1-hydroxyethyl)-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one
• Synonyms: 17α,20β-Dihydroxyprogesterone; 17α-Hydroxy-20β-dihydroprogesterone; 4-Pregnene-17α,20β-diol-3-one; Maturation Inducing hormone (MIF); 17α,20β-Dihydroxy-4-pregnen-3-one; 17α, 20β-Dihydroxy-4-pregnen-3-one; MIH; Maturation-inducing Hormone; 4-Pregnen-17α,20β-diol-3-one

Database IDs

• CAS Number: 1662-06-2
• MDL Number: MFCD00010485
• PubChem SID: 162228598; 24898755
• PubChem CID: 16219879

CALCULATED PROPERTIES

• Acid pKa: 13.417379
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 3.015665
• LogD (pH = 7.4): 3.0156646
• Log P: 3.015665
• Molar Refractivity: 95.0305 cm^3
• Polarizability: 37.560345 Å^3
• Polar Surface Area: 57.53 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: crystalline; White to Off-White Solid
• Melting Point: 194-196°C

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: Store in Freezer
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

DETAILS

Sigma Aldrich - P6285

Biochem/physiol Actions
17α,20β-Dihydroxy-4-pregnen-3-one, also known as maturation-inducing steroid (MIS), is the most potent steroid for inducing final oocyte maturation in several species of fish.