5-[(1S,2R,3R,5S)-3,5-dihydroxy-2-[(3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]pent-3-enoic acid

• ChemBase ID: 155743
• Molecular Formular: C18H30O5
• Molecular Mass: 326.4278
• Monoisotopic Mass: 326.20932406
• SMILES: CCCCC[C@@H](C=C[C@H]1[C@@H](C[C@@H]([C@H]1C/C=C/CC(=O)O)O)O)O
• Canonical SMILES: CCCCC[C@@H](C=C[C@H]1[C@H](O)C[C@@H]([C@H]1C/C=C/CC(=O)O)O)O
• InChI: InChI=1S/C18H30O5/c1-2-3-4-7-13(19)10-11-15-14(16(20)12-17(15)21)8-5-6-9-18(22)23/h5-6,10-11,13-17,19-21H,2-4,7-9,12H2,1H3,(H,22,23)/t13-,14-,15+,16-,17+/m0/s1
• InChIKey: IDKLJIUIJUVJNR-ZOFXXKQRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-[(1S,2R,3R,5S)-3,5-dihydroxy-2-[(3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]pent-3-enoic acid
• IUPAC Traditional name: 5-[(1S,2R,3R,5S)-3,5-dihydroxy-2-[(3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]pent-3-enoic acid
• Synonyms: 2,3-Di-nor-8-isoprostaglandin F2α

Database IDs

• CAS Number: 221664-05-7
• MDL Number: MFCD03411993
• PubChem SID: 162249881
• PubChem CID: 71312216

CALCULATED PROPERTIES

• Acid pKa: 4.407789
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): 0.59751624
• LogD (pH = 7.4): -1.1600686
• Log P: 1.721917
• Molar Refractivity: 91.2687 cm^3
• Polarizability: 35.058247 Å^3
• Polar Surface Area: 97.99 Å^2
• Rotatable Bonds: 10
• 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%
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C18H30O5

DETAILS

Sigma Aldrich - D4565

Other Notes
Metabolite of 8-iso-PGF2α