[2-(octadec-9-enamido)ethoxy]phosphonic acid

• ChemBase ID: 155842
• Molecular Formular: C20H40NO5P
• Molecular Mass: 405.509061
• Monoisotopic Mass: 405.26441002
• SMILES: CCCCCCCC/C=C/CCCCCCCC(=O)NCCOP(=O)(O)O
• Canonical SMILES: CCCCCCCC/C=C/CCCCCCCC(=O)NCCOP(=O)(O)O
• InChI: InChI=1S/C20H40NO5P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(22)21-18-19-26-27(23,24)25/h9-10H,2-8,11-19H2,1H3,(H,21,22)(H2,23,24,25)
• InChIKey: BCSUWOZFWWBYSX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [2-(octadec-9-enamido)ethoxy]phosphonic acid
• IUPAC Traditional name: 2-(octadec-9-enamido)ethoxyphosphonic acid
• Synonyms: (Z)-N-[2-(Phosphonooxy)ethyl]-9-octadecenamide; NAEPA

Database IDs

• CAS Number: 24435-25-4
• MDL Number: MFCD06798344
• PubChem SID: 162249980
• PubChem CID: 17757220

CALCULATED PROPERTIES

• Acid pKa: 1.5433087
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 2.9853506
• LogD (pH = 7.4): 2.1242018
• Log P: 5.3868637
• Molar Refractivity: 111.2863 cm^3
• Polarizability: 43.409714 Å^3
• Polar Surface Area: 95.86 Å^2
• Rotatable Bonds: 19
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: soluble28 mg/mL; H2O: soluble
• Apperance: white solid
• Melting Point: 75.8-84.0 °C

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98 (TLC)
• Empirical Formula (Hill Notation): C20H40NO5P

DETAILS

Sigma Aldrich - N0912

Biochem/physiol Actions
Selective lysophosphatidic acid-1 (LPA1) receptor agonist; LPA mimetic