7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]-N-(2-hydroxyethyl)hept-5-enamide

• ChemBase ID: 155674
• Molecular Formular: C22H39NO5
• Molecular Mass: 397.54876
• Monoisotopic Mass: 397.28282335
• SMILES: CCCCC[C@@H](C=C[C@H]1[C@@H](C[C@@H]([C@@H]1C/C=C/CCCC(=O)NCCO)O)O)O
• Canonical SMILES: CCCCC[C@@H](C=C[C@H]1[C@H](O)C[C@@H]([C@@H]1C/C=C/CCCC(=O)NCCO)O)O
• InChI: InChI=1S/C22H39NO5/c1-2-3-6-9-17(25)12-13-19-18(20(26)16-21(19)27)10-7-4-5-8-11-22(28)23-14-15-24/h4,7,12-13,17-21,24-27H,2-3,5-6,8-11,14-16H2,1H3,(H,23,28)/t17-,18+,19+,20-,21+/m0/s1
• InChIKey: XCVCLIRZZCGEMU-XIYVOTBMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]-N-(2-hydroxyethyl)hept-5-enamide
• IUPAC Traditional name: 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]-N-(2-hydroxyethyl)hept-5-enamide
• Synonyms: Dinoprost ethanolamide; N-(2-Hydroxyethyl)-9α,11α,15S-trihydroxy-prosta-5Z,13E-dien-1-amide; Prostaglandin F2α ethanolamide

Database IDs

• EC Number: 200-578-6
• MDL Number: MFCD03411991
• PubChem SID: 162249812
• PubChem CID: 71312196

CALCULATED PROPERTIES

• Acid pKa: 14.446371
• H Acceptors: 5
• H Donor: 5
• LogD (pH = 5.5): 1.3376852
• LogD (pH = 7.4): 1.3376858
• Log P: 1.3376858
• Molar Refractivity: 113.4819 cm^3
• Polarizability: 43.73197 Å^3
• Polar Surface Area: 110.02 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Flash Point: 14 °C; 57.2 °F

Safety Information

• European Hazard Symbols: Flammable (F)
• UN Number: 1170
• German water hazard class: 2
• Hazard Class: 3
• Packing Group: 2
• Risk Statements: 11
• Safety Statements: 7-16
• GHS Pictograms: GHS02
• GHS Signal Word: Danger
• GHS Hazard statements: H225
• GHS Precautionary statements: P210
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1170 3/PG 2
• Storage Temperature: -20°C

Product Information

• Purity: ≥98%
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C22H39NO5

DETAILS

Sigma Aldrich - P6738

Biochem/physiol Actions
The end-product of the reaction of arachidonyl ethanolamide (AEA), an endogenous ligand for brain cannabinoid receptor, with COX-2.
Physical form
Solution in ethanol