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

• ChemBase ID: 162128
• Molecular Formular: C28H52N3O7PS
• Molecular Mass: 605.767141
• Monoisotopic Mass: 605.32635865
• SMILES: N1C(=O)N[C@@H]2[C@@H](SC[C@H]12)CCCCC(=O)NC([C@@H](/C=C/CCCCCCCCCCCCC)O)COP(=O)(O)O
• Canonical SMILES: CCCCCCCCCCCCC/C=C/[C@H](C(NC(=O)CCCC[C@@H]1SC[C@H]2[C@@H]1NC(=O)N2)COP(=O)(O)O)O
• InChI: InChI=1S/C28H52N3O7PS/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-17-24(32)22(20-38-39(35,36)37)29-26(33)19-16-15-18-25-27-23(21-40-25)30-28(34)31-27/h14,17,22-25,27,32H,2-13,15-16,18-21H2,1H3,(H,29,33)(H2,30,31,34)(H2,35,36,37)/b17-14+/t22?,23-,24+,25-,27-/m0/s1
• InChIKey: YUVSZTHGPGQBCL-KNRYMFASSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(3R,4E)-2-{5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]pentanamido}-3-hydroxyoctadec-4-en-1-yl]oxy}phosphonic acid
• IUPAC Traditional name: [(3R,4E)-2-{5-[(3aS,4S,6aR)-2-oxo-hexahydrothieno[3,4-d]imidazolidin-4-yl]pentanamido}-3-hydroxyoctadec-4-en-1-yl]oxyphosphonic acid
• Synonyms: (3aS,4S,6aR)-Hexahydro-N-[(1S,2R,3E)-2-hydroxy-1-[(phosphonooxy)methyl]-3-heptadecen-1-yl]-2-oxo-1H-thieno[3,4-d]imidazole-4-pentanamide; N-Biotinyl D-erythro-Sphingosine-1-phosphate

Database IDs

• CAS Number: 1093733-24-4
• PubChem SID: 162256263
• PubChem CID: 71314015

CALCULATED PROPERTIES

• Acid pKa: 1.5285488
• H Acceptors: 6
• H Donor: 6
• LogD (pH = 5.5): 2.4005609
• LogD (pH = 7.4): 1.5216316
• Log P: 4.642215
• Molar Refractivity: 159.6159 cm^3
• Polarizability: 62.77652 Å^3
• Polar Surface Area: 157.22 Å^2
• Rotatable Bonds: 23
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - B397810

A biotinylated substrate conjugate used for performing ELISA on water-soluble ligands. Used for ceramide phosphate sphingosine synthesis.

REFERENCES

• De Ceuster, P., et al.: Biochem. J., 311, 139 (1995)
• Pettus, B., et al.: J. Biol. Chem., 279, 11320 (1995)