7-[(1R,2R,5S)-5-hydroxy-2-[(3S)-3-hydroxy-5-phenylpent-1-en-1-yl]-3-oxocyclopentyl]hept-5-enoic acid

• ChemBase ID: 155760
• Molecular Formular: C23H30O5
• Molecular Mass: 386.4813
• Monoisotopic Mass: 386.20932406
• SMILES: c1ccc(cc1)CC[C@@H](C=C[C@@H]1[C@H]([C@H](CC1=O)O)C/C=C/CCCC(=O)O)O
• Canonical SMILES: OC(=O)CCC/C=C/C[C@H]1[C@@H](O)CC(=O)[C@@H]1C=C[C@H](CCc1ccccc1)O
• InChI: InChI=1S/C23H30O5/c24-18(13-12-17-8-4-3-5-9-17)14-15-20-19(21(25)16-22(20)26)10-6-1-2-7-11-23(27)28/h1,3-6,8-9,14-15,18-21,24-25H,2,7,10-13,16H2,(H,27,28)/t18-,19+,20+,21-/m0/s1
• InChIKey: OAQGPAZDRCBBLD-BQJUDKOJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-[(1R,2R,5S)-5-hydroxy-2-[(3S)-3-hydroxy-5-phenylpent-1-en-1-yl]-3-oxocyclopentyl]hept-5-enoic acid
• IUPAC Traditional name: 7-[(1R,2R,5S)-5-hydroxy-2-[(3S)-3-hydroxy-5-phenylpent-1-en-1-yl]-3-oxocyclopentyl]hept-5-enoic acid
• Synonyms: 17-Phenyl-tri-norprostaglandin D2

Database IDs

• MDL Number: MFCD01746791
• PubChem SID: 162249898
• PubChem CID: 71312217

CALCULATED PROPERTIES

• Acid pKa: 4.404553
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 2.3425534
• LogD (pH = 7.4): 0.585448
• Log P: 3.4699368
• Molar Refractivity: 110.3281 cm^3
• Polarizability: 42.1718 Å^3
• Polar Surface Area: 94.83 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: methyl acetate solution
• Flash Point: -16 °C; 3 °F

Safety Information

• European Hazard Symbols: Flammable (F); Irritant (Xi)
• UN Number: 1231
• German water hazard class: 1
• Hazard Class: 3
• Packing Group: 2
• Risk Statements: 11-36-66-67
• Safety Statements: 16-26-29-33
• RID/ADR: UN 1231 3/PG 2
• Storage Temperature: -20°C

Product Information

• Purity: ≥98%
• Empirical Formula (Hill Notation): C23H30O5

DETAILS

Sigma Aldrich - P6615

Application
Chemically stable analog of prostaglandin D2.