[(1S,10R,11S,15S)-15-methyl-14-oxotetracyclo[8.7.0.02,7.011,15]heptadeca-2,4,6-trien-5-yl]oxidanesulfonic acid; piperazine

• ChemBase ID: 154856
• Molecular Formular: C22H32N2O5S
• Molecular Mass: 436.56488
• Monoisotopic Mass: 436.20319313
• SMILES: C[C@]12CC[C@@H]3c4ccc(cc4CC[C@H]3[C@@H]1CCC2=O)OS(=O)(=O)O.C1CNCCN1
• Canonical SMILES: C1CNCCN1.O=C1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCc2c1ccc(c2)OS(=O)(=O)O
• InChI: InChI=1S/C18H22O5S.C4H10N2/c1-18-9-8-14-13-5-3-12(23-24(20,21)22)10-11(13)2-4-15(14)16(18)6-7-17(18)19;1-2-6-4-3-5-1/h3,5,10,14-16H,2,4,6-9H2,1H3,(H,20,21,22);5-6H,1-4H2/t14-,15-,16+,18+;/m1./s1
• InChIKey: HZEQBCVBILBTEP-ZFINNJDLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(1S,10R,11S,15S)-15-methyl-14-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2,4,6-trien-5-yl]oxidanesulfonic acid; piperazine
• IUPAC Traditional name: OGEN; piperazine
• Synonyms: 3-(Sulfooxy)-estra-1,3,5(10)-trien-17-one : piperazine (1:1); Estrone sulfate piperazine salt; Estropipate; Harmogen; Ogen; Estropipate

Database IDs

• CAS Number: 477-24-7(freeacid)
• EC Number: 230-696-3
• MDL Number: MFCD00867399
• PubChem SID: 162248994
• PubChem CID: 5284555

CALCULATED PROPERTIES

• Acid pKa: -1.7480068
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 1.4573227
• LogD (pH = 7.4): 1.457317
• Log P: 3.8337157
• Molar Refractivity: 89.0742 cm^3
• Polarizability: 35.487312 Å^3
• Polar Surface Area: 80.67 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥24 mg/mL
• Apperance: white to tan powder
• Optical Rotation: [α]/D 100 to 120°, c = 1 in DMSO

Safety Information

• RTECS: KG7785000
• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 45-22
• Safety Statements: 53-45
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H302-H350
• GHS Precautionary statements: P201-P308 + P313
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C18H22O5S·C4H10N2

DETAILS

Sigma Aldrich - E2661

Biochem/physiol Actions
Estropipate is the piperazine salt of the estrogen receptor agonist estrone-3-sulfate and a potent, specific inhibitor of the organic anion transporting polypeptide 1B1 (OATP1B1, IC50 = 60 nM).