7-{2-[(3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopent-1-en-1-yl}hept-5-enoic acid

• ChemBase ID: 2050
• Molecular Formular: C20H30O4
• Molecular Mass: 334.4498
• Monoisotopic Mass: 334.21440944
• SMILES: CCCCC[C@H](O)/C=C/C1=C(C/C=C/CCCC(=O)O)C(=O)CC1
• Canonical SMILES: CCCCC[C@@H](/C=C/C1=C(C/C=C/CCCC(=O)O)C(=O)CC1)O
• InChI: InChI=1S/C20H30O4/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/h4,7,12,14,17,21H,2-3,5-6,8-11,13,15H2,1H3,(H,23,24)/b7-4+,14-12+/t17-/m0/s1
• InChIKey: PRFXRIUZNKLRHM-OSJNIVAESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-{2-[(3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopent-1-en-1-yl}hept-5-enoic acid; (5E)-7-{2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopent-1-en-1-yl}hept-5-enoic acid
• IUPAC Traditional name: 7-{2-[(3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopent-1-en-1-yl}hept-5-enoic acid; @prostaglandin B2
• Synonyms: (5Z,13E,15S)-15-Hydroxy-9-oxoprosta-5,8(12),13-trien-1-oic acid; PGB2; Prostaglandin B2; Prostaglandin B2

Database IDs

• CAS Number: 13367-85-6
• MDL Number: MFCD00065730
• Beilstein Number: 2153006
• PubChem SID: 160965505; 46507640; 24898630
• PubChem CID: 6441243

CALCULATED PROPERTIES

JChem

• Acid pKa: 4.2537546
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 2.916907
• LogD (pH = 7.4): 1.1886859
• Log P: 4.1848574
• Molar Refractivity: 98.6059 cm^3
• Polarizability: 37.313618 Å^3
• Polar Surface Area: 74.6 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 4.07
• LOG S: -4.05
• Solubility (Water): 2.99e-02 g/l

PROPERTIES

Physical Property

• Solubility: acetone: soluble10 mg/mL, clear; DMSO: ~50 mg/mL; ethanol: ~100 mg/mL; PBS, pH 7.2: ~2 mg/mL
• Apperance: solution
• Flash Point: 15.8 °F; -9 °C

Safety Information

• European Hazard Symbols: Flammable (F); Irritant (Xi); Harmful (Xn)
• UN Number: 1231
• German water hazard class: 2; 3
• Hazard Class: 3
• Packing Group: 2
• Risk Statements: 11-36-66-67; 20/21/22
• Safety Statements: 16-26; 36/37
• GHS Pictograms: GHS02; GHS07
• GHS Signal Word: Danger; Warning
• GHS Hazard statements: H225-H319-H336; H302-H312-H332
• GHS Precautionary statements: P210-P261-P305 + P351 + P338; P280
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves; Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1231 3/PG 2
• Supplemental Hazard Statements: Repeated exposure may cause skin dryness or cracking.
• Storage Temperature: -20°C

Product Information

• Purity: ≥98%; ≥98.0% (TLC)
• Biological Source: synthetic
• Empirical Formula (Hill Notation): C20H30O4

DETAILS

DrugBank - DB02304

Drug information: experimental

Sigma Aldrich - P5390

Biochem/physiol Actions
Primary prostaglandin of osteoblasts; induces pulmonary hypertension.
Preparation Note
PGB2 is provided as a solution in methyl acetate. To change the solvent, evaporate the methyl acetate under a gentle stream of nitrogen and immediately add the solvent of choice. PGB2, purged with an inert gas, is soluble in ethanol at ~100 mg/mL, DMSO at ~50 mg/mL and in dimethyl formamide at ~ 75 mg/mL.
Physical form
Prostaglandin B2 is supplied as a solution in methyl acetate