7-{2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopent-1-en-1-yl}heptanoic acid

• ChemBase ID: 134169
• Molecular Formular: C20H32O4
• Molecular Mass: 336.46568
• Monoisotopic Mass: 336.2300595
• SMILES: CCCCC[C@@H](/C=C/C1=C(C(=O)CC1)CCCCCCC(=O)O)O
• Canonical SMILES: CCCCC[C@@H](/C=C/C1=C(CCCCCCC(=O)O)C(=O)CC1)O
• InChI: InChI=1S/C20H32O4/c1-2-3-6-9-17(21)14-12-16-13-15-19(22)18(16)10-7-4-5-8-11-20(23)24/h12,14,17,21H,2-11,13,15H2,1H3,(H,23,24)/b14-12+/t17-/m0/s1
• InChIKey: YBHMPNRDOVPQIN-VSOYFRJCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-{2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopent-1-en-1-yl}heptanoic acid; 7-{2-[(3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopent-1-en-1-yl}heptanoic acid
• IUPAC Traditional name: prostaglandin-B1; 7-{2-[(3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopent-1-en-1-yl}heptanoic acid
• Synonyms: (13E,15S)-15-Hydroxy-9-oxoprosta-8(12),13-dien-1-oic acid; PGB1; Prostaglandin B1

Database IDs

• CAS Number: 13345-51-2
• MDL Number: MFCD00036679
• Beilstein Number: 2004447
• PubChem SID: 24898612; 162228446
• PubChem CID: 5280388

CALCULATED PROPERTIES

• Acid pKa: 4.3035073
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 3.3255172
• LogD (pH = 7.4): 1.5863414
• Log P: 4.546779
• Molar Refractivity: 97.4893 cm^3
• Polarizability: 37.555786 Å^3
• Polar Surface Area: 74.6 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: acetone: soluble20 mg/mL, clear, colorless to light yellow
• Apperance: white to light yellow powder

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); ≥99.0% (TLC)
• Biological Source: synthetic
• Empirical Formula (Hill Notation): C20H32O4

DETAILS

Sigma Aldrich - P5265

Other Notes
Metabolite of prostaglandin E.

Sigma Aldrich - 82467

Other Notes
Biochemical characterization of prostaglandin 19-hydroxylase of seminal vesicles1; Femtomole analysis of prostaglandin pharmaceuticals2