{[(2S,3R,4E)-18-{5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]pentanamido}-2-amino-3-hydroxyoctadec-4-en-1-yl]oxy}phosphonic acid

• ChemBase ID: 160481
• Molecular Formular: C28H53N4O7PS
• Molecular Mass: 620.781781
• Monoisotopic Mass: 620.33725769
• SMILES: N1C(=O)N[C@H]2CS[C@@H](CCCCC(=O)NCCCCCCCCCCCCC/C=C/[C@H]([C@H](COP(=O)(O)O)N)O)[C@@H]12
• Canonical SMILES: O=C(NCCCCCCCCCCCCC/C=C/[C@H]([C@H](COP(=O)(O)O)N)O)CCCC[C@@H]1SC[C@H]2[C@@H]1NC(=O)N2
• InChI: InChI=1S/C28H53N4O7PS/c29-22(20-39-40(36,37)38)24(33)16-12-10-8-6-4-2-1-3-5-7-9-11-15-19-30-26(34)18-14-13-17-25-27-23(21-41-25)31-28(35)32-27/h12,16,22-25,27,33H,1-11,13-15,17-21,29H2,(H,30,34)(H2,31,32,35)(H2,36,37,38)/b16-12+/t22-,23-,24+,25-,27-/m0/s1
• InChIKey: JHROEHVYJZWKKP-RPRIXWAOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(2S,3R,4E)-18-{5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]pentanamido}-2-amino-3-hydroxyoctadec-4-en-1-yl]oxy}phosphonic acid
• IUPAC Traditional name: [(2S,3R,4E)-18-{5-[(3aS,4S,6aR)-2-oxo-hexahydrothieno[3,4-d]imidazolidin-4-yl]pentanamido}-2-amino-3-hydroxyoctadec-4-en-1-yl]oxyphosphonic acid
• Synonyms: (3aS,4S,6aR)-N-[(14E,16R,17S)-17-Amino-16,18-dihydroxy-14-octadecen-1-yl]hexahydro-2-oxo-1H-thieno[3,4-d]imidazole-4-pentanamide 1-Phosphate; erythro-ω-Amino Sphingosine Biotinamide Phosphate

Database IDs

• PubChem SID: 162254616
• PubChem CID: 46891741

CALCULATED PROPERTIES

• Acid pKa: 1.5255809
• H Acceptors: 7
• H Donor: 7
• LogD (pH = 5.5): 2.2135181
• LogD (pH = 7.4): 1.3440033
• Log P: 2.2488625
• Molar Refractivity: 163.2021 cm^3
• Polarizability: 64.306015 Å^3
• Polar Surface Area: 183.24 Å^2
• Rotatable Bonds: 24
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - A629235

Bioactive sphingolipids with an attached label or tag are useful tools for localisation, binding and metabolism studies and as assay substrates. Used in an assay for sphingosine kinase activity using biotinylated sphingosine and streptavidin-coated membra

REFERENCES

• Wisniewski, D., et al.: Anal. Biochem., 274, 220 (1999)
• Olivera, A., et al.: J. Biol. Chem., 278, 46452 (1999)