(5E)-7-[(1S,2S,3R)-3-hydroxy-5-oxo-2-[(1E)-3-oxooct-1-en-1-yl]cyclopentyl]hept-5-enoic acid

• ChemBase ID: 4829
• Molecular Formular: C20H30O5
• Molecular Mass: 350.4492
• Monoisotopic Mass: 350.20932406
• SMILES: CCCCCC(=O)/C=C/[C@@H]1[C@H](O)CC(=O)[C@H]1C/C=C/CCCC(=O)O
• Canonical SMILES: CCCCCC(=O)/C=C/[C@@H]1[C@H](O)CC(=O)[C@H]1C/C=C/CCCC(=O)O
• InChI: InChI=1S/C20H30O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,16-17,19,23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4+,13-12+/t16-,17-,19+/m0/s1
• InChIKey: YRTJDWROBKPZNV-DYTRGIJQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5E)-7-[(1S,2S,3R)-3-hydroxy-5-oxo-2-[(1E)-3-oxooct-1-en-1-yl]cyclopentyl]hept-5-enoic acid
• IUPAC Traditional name: (5E)-7-[(1S,2S,3R)-3-hydroxy-5-oxo-2-[(1E)-3-oxooct-1-en-1-yl]cyclopentyl]hept-5-enoic acid
• Synonyms: (5E,13E)-11-HYDROXY-9,15-DIOXOPROSTA-5,13-DIEN-1-OIC ACID

Database IDs

• PubChem SID: 160968261; 99443648
• PubChem CID: 46937058

CALCULATED PROPERTIES

JChem

• Acid pKa: 4.303359
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 2.4152086
• LogD (pH = 7.4): 0.6760632
• Log P: 3.6366086
• Molar Refractivity: 98.5377 cm^3
• Polarizability: 37.644333 Å^3
• Polar Surface Area: 91.67 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.27
• LOG S: -3.78
• Solubility (Water): 5.83e-02 g/l

DETAILS

DrugBank - DB07177

Drug information: experimental