[(1S,2R,5S,10S,11S,14S,15S)-14-acetyl-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-7-en-5-yl]oxidanesulfonic acid sodium

• ChemBase ID: 133325
• Molecular Formular: C21H32NaO5S
• Molecular Mass: 419.53055
• Monoisotopic Mass: 419.18681441
• SMILES: CC(=O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]1[C@H]2CC=C2[C@@]1(CC[C@@H](C2)OS(=O)(=O)O)C)C.[Na]
• Canonical SMILES: CC(=O)[C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CC=C2[C@]1(C)CC[C@@H](C2)OS(=O)(=O)O.[Na]
• InChI: InChI=1S/C21H32O5S.Na/c1-13(22)17-6-7-18-16-5-4-14-12-15(26-27(23,24)25)8-10-20(14,2)19(16)9-11-21(17,18)3;/h4,15-19H,5-12H2,1-3H3,(H,23,24,25);/t15-,16-,17+,18-,19-,20-,21+;/m0./s1
• InChIKey: DUBUGTJRMPFLOO-UTNKIXDHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(1S,2R,5S,10S,11S,14S,15S)-14-acetyl-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-7-en-5-yl]oxidanesulfonic acid sodium
• IUPAC Traditional name: pregnenolone sulfate sodium
• Synonyms: 3β-Hydroxy-5-pregnen-20-one 3-sulfate; 3-Hydroxypregn-5-en-20-one sulfate; 5-Pregnen-3β-ol-20-one sulfate; Pregnenolone sulfate sodium salt

Database IDs

• MDL Number: MFCD00056177
• PubChem SID: 162227602; 24278112
• PubChem CID: 16219827

CALCULATED PROPERTIES

• Acid pKa: -1.3632754
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 1.2599596
• LogD (pH = 7.4): 1.2599456
• Log P: 3.6363442
• Molar Refractivity: 103.7485 cm^3
• Polarizability: 41.663044 Å^3
• Polar Surface Area: 80.67 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: soluble2 mg/mL; methanol and water: soluble1.93 mg/mL
• Melting Point: 192 °C(lit.)

Safety Information

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

Pharmacology Properties

• Gene Information: human ... GABRA1(2554), GABRA2(2555), GABRA3(2556), GABRA4(2557), GABRA5(2558), GABRA6(2559), GABRB1(2560), GABRB2(2561), GABRB3(2562)

DETAILS

Sigma Aldrich - P162

Biochem/physiol Actions
Neurosteroid that antagonizes the GABAA receptor chloride channel.