7-[(1R,2R,3S,5S)-3-hydroxy-5-[(4-phenylphenyl)methoxy]-2-(piperidin-1-yl)cyclopentyl]hept-4-enoic acid hydrochloride

• ChemBase ID: 154180
• Molecular Formular: C30H40ClNO4
• Molecular Mass: 514.0959
• Monoisotopic Mass: 513.26458645
• SMILES: c1ccc(cc1)c1ccc(cc1)CO[C@H]1C[C@@H]([C@@H]([C@H]1CC/C=C/CCC(=O)O)N1CCCCC1)O.Cl
• Canonical SMILES: OC(=O)CC/C=C/CC[C@H]1[C@@H](OCc2ccc(cc2)c2ccccc2)C[C@@H]([C@@H]1N1CCCCC1)O.Cl
• InChI: InChI=1S/C30H39NO4.ClH/c32-27-21-28(35-22-23-15-17-25(18-16-23)24-11-5-3-6-12-24)26(13-7-1-2-8-14-29(33)34)30(27)31-19-9-4-10-20-31;/h1-3,5-6,11-12,15-18,26-28,30,32H,4,7-10,13-14,19-22H2,(H,33,34);1H/t26-,27-,28-,30+;/m0./s1
• InChIKey: ZYOBZRTZRQKKNC-TZGCDWQGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-[(1R,2R,3S,5S)-3-hydroxy-5-[(4-phenylphenyl)methoxy]-2-(piperidin-1-yl)cyclopentyl]hept-4-enoic acid hydrochloride
• IUPAC Traditional name: 7-[(1R,2R,3S,5S)-3-hydroxy-5-[(4-phenylphenyl)methoxy]-2-(piperidin-1-yl)cyclopentyl]hept-4-enoic acid hydrochloride
• Synonyms: (4Z)-7-[(1R,2R,3S,5S)-5-([1,1′-Biphenyl]-4-ylmethoxy)-3-hydroxy-2-(1-piperidinyl)cyclopentyl]-4-heptenoic acid hydrochloride; GR 32191B

Database IDs

• CAS Number: 87248-13-3
• MDL Number: MFCD04113055
• PubChem SID: 162248319
• PubChem CID: 6435456

CALCULATED PROPERTIES

• Acid pKa: 4.012908
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 2.5252316
• LogD (pH = 7.4): 2.5358295
• Log P: 2.536084
• Molar Refractivity: 140.7915 cm^3
• Polarizability: 56.096622 Å^3
• Polar Surface Area: 70.0 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: ~16 mg/mL
• Apperance: off-white solid
• Melting Point: 127-128 °C

Safety Information

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

Product Information

• Purity: ≥98% (HPLC)
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C30H40NO4Cl

DETAILS

Sigma Aldrich - G5044

Biochem/physiol Actions
Selective TP prostanoid receptor antagonist. Inhibits U-46619-induced contraction of guinea pig trachea with IC50=1.8 nM.
Legal Information
Manufactured and sold under agreement from Glaxo-Smith-Kline