5-[(3aS,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]-N-[(14E,16R,17S)-17-amino-16,18-dihydroxyoctadec-14-en-1-yl]pentanamide

• ChemBase ID: 160479
• Molecular Formular: C28H52N4O4S
• Molecular Mass: 540.80188
• Monoisotopic Mass: 540.37092716
• SMILES: N1C(=O)N[C@H]2CSC(CCCCC(=O)NCCCCCCCCCCCCC/C=C/[C@H]([C@H](CO)N)O)[C@@H]12
• Canonical SMILES: OC[C@@H]([C@@H](/C=C/CCCCCCCCCCCCCNC(=O)CCCCC1SC[C@H]2[C@@H]1NC(=O)N2)O)N
• InChI: InChI=1S/C28H52N4O4S/c29-22(20-33)24(34)16-12-10-8-6-4-2-1-3-5-7-9-11-15-19-30-26(35)18-14-13-17-25-27-23(21-37-25)31-28(36)32-27/h12,16,22-25,27,33-34H,1-11,13-15,17-21,29H2,(H,30,35)(H2,31,32,36)/b16-12+/t22-,23-,24+,25?,27-/m0/s1
• InChIKey: NYQVYZZGZCNEMF-BSCTWARMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-[(3aS,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]-N-[(14E,16R,17S)-17-amino-16,18-dihydroxyoctadec-14-en-1-yl]pentanamide
• IUPAC Traditional name: 5-[(3aS,6aR)-2-oxo-hexahydrothieno[3,4-d]imidazolidin-4-yl]-N-[(14E,16R,17S)-17-amino-16,18-dihydroxyoctadec-14-en-1-yl]pentanamide
• 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; erythro-ω-Amino Sphingosine Biotinamide

Database IDs

• CAS Number: 752987-57-8
• PubChem SID: 162254614
• PubChem CID: 71313353

CALCULATED PROPERTIES

• Acid pKa: 13.40061
• H Acceptors: 5
• H Donor: 6
• LogD (pH = 5.5): 0.43023106
• LogD (pH = 7.4): 1.5705565
• Log P: 3.3846357
• Molar Refractivity: 152.3292 cm^3
• Polarizability: 59.987343 Å^3
• Polar Surface Area: 136.71 Å^2
• Rotatable Bonds: 22
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - A629230

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)