4-{2-[(1S,2R,10S,11S,14S,15S)-2,15-dimethyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadec-6-en-14-yl]-2-oxoethoxy}-4-oxobutanoic acid

• ChemBase ID: 131624
• Molecular Formular: C25H34O6
• Molecular Mass: 430.53386
• Monoisotopic Mass: 430.23553881
• SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2C(=O)COC(=O)CCC(=O)O)CCC1=CC(=O)CC[C@]31C
• Canonical SMILES: OC(=O)CCC(=O)OCC(=O)[C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCC2=CC(=O)CC[C@]12C
• InChI: InChI=1S/C25H34O6/c1-24-11-9-16(26)13-15(24)3-4-17-18-5-6-20(25(18,2)12-10-19(17)24)21(27)14-31-23(30)8-7-22(28)29/h13,17-20H,3-12,14H2,1-2H3,(H,28,29)/t17-,18-,19-,20+,24-,25-/m0/s1
• InChIKey: CYWICJWKZPXJSA-PQWRYPMOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{2-[(1S,2R,10S,11S,14S,15S)-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-14-yl]-2-oxoethoxy}-4-oxobutanoic acid
• IUPAC Traditional name: 4-{2-[(1S,2R,10S,11S,14S,15S)-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-14-yl]-2-oxoethoxy}-4-oxobutanoic acid
• Synonyms: 21-Hydroxy-4-pregnene-3,20-dione 21-hemisuccinate; 21-Hydroxyprogesterone 21-hemisuccinate; 4-Pregnen-21-ol-3,20-dione 21-hemisuccinate; Cortexone 21-hemisuccinate; Deoxycorticosterone 21-hemisuccinate

Database IDs

• CAS Number: 10215-74-4
• EC Number: 233-528-7
• MDL Number: MFCD00133246
• PubChem SID: 162225901; 24893428
• PubChem CID: 112092

CALCULATED PROPERTIES

• Acid pKa: 3.742547
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 1.8396454
• LogD (pH = 7.4): 0.30951628
• Log P: 3.5973444
• Molar Refractivity: 114.4523 cm^3
• Polarizability: 45.08079 Å^3
• Polar Surface Area: 97.74 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

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

Product Information

• Classification: Derivatives & analogs of Natural Compounds

DETAILS

Sigma Aldrich - D1400

Biochem/physiol Actions
Demonstrated multi-site antiglucocorticoid activity in vivo.1