{[(3R,4E)-2-butanamido-3-hydroxyoctadec-4-en-1-yl]oxy}phosphonic acid

• ChemBase ID: 163986
• Molecular Formular: C22H44NO6P
• Molecular Mass: 449.561621
• Monoisotopic Mass: 449.29062476
• SMILES: C(CCCCCCCCCCC/C=C/[C@H](C(COP(=O)(O)O)NC(=O)CCC)O)C
• Canonical SMILES: CCCCCCCCCCCCC/C=C/[C@H](C(NC(=O)CCC)COP(=O)(O)O)O
• InChI: InChI=1S/C22H44NO6P/c1-3-5-6-7-8-9-10-11-12-13-14-15-16-18-21(24)20(19-29-30(26,27)28)23-22(25)17-4-2/h16,18,20-21,24H,3-15,17,19H2,1-2H3,(H,23,25)(H2,26,27,28)/b18-16+/t20?,21-/m1/s1
• InChIKey: BVVVVEVXBZVIFX-VPVVUANGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(3R,4E)-2-butanamido-3-hydroxyoctadec-4-en-1-yl]oxy}phosphonic acid
• IUPAC Traditional name: [(3R,4E)-2-butanamido-3-hydroxyoctadec-4-en-1-yl]oxyphosphonic acid
• Synonyms: N-[(1S,2R,3E)-2-Hydroxy-1-[(phosphonooxy)methyl]-3-heptadecenyl]butanamide; N-Butyl-D-sphingosine-1-phosphate; Butyl Ceramide-1-phosphate; N-Butanoyl-D-erythro-sphingosine-1-phosphate; C4 Ceramide-1-phosphate

Database IDs

• PubChem SID: 162258121
• PubChem CID: 71314644

CALCULATED PROPERTIES

• Acid pKa: 1.5200034
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): 3.002897
• LogD (pH = 7.4): 2.1239672
• Log P: 5.4069653
• Molar Refractivity: 121.4366 cm^3
• Polarizability: 47.727734 Å^3
• Polar Surface Area: 116.09 Å^2
• Rotatable Bonds: 20
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Brown Solid
• Melting Point: 61-63°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - C262555

Ceramide-1-phosphate blocks apoptosis through inhibition of acid sphingomyelinase in macrophages.