N-[(2S,3R,4E)-1,3-dihydroxyoctadec-4-en-2-yl]-6-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]hexanamide

• ChemBase ID: 132732
• Molecular Formular: C30H49N5O6
• Molecular Mass: 575.73996
• Monoisotopic Mass: 575.36828431
• SMILES: CCCCCCCCCCCCC/C=C/[C@H]([C@H](CO)NC(=O)CCCCCNc1ccc(c2c1non2)[N+](=O)[O-])O
• Canonical SMILES: CCCCCCCCCCCCC/C=C/[C@H]([C@@H](NC(=O)CCCCCNc1ccc(c2c1non2)[N+](=O)[O-])CO)O
• InChI: InChI=1S/C30H49N5O6/c1-2-3-4-5-6-7-8-9-10-11-12-13-15-18-27(37)25(23-36)32-28(38)19-16-14-17-22-31-24-20-21-26(35(39)40)30-29(24)33-41-34-30/h15,18,20-21,25,27,31,36-37H,2-14,16-17,19,22-23H2,1H3,(H,32,38)/b18-15+/t25-,27+/m0/s1
• InChIKey: HZIRBXILQRLFIK-VPZZKNKNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2S,3R,4E)-1,3-dihydroxyoctadec-4-en-2-yl]-6-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]hexanamide
• IUPAC Traditional name: nbd-ceramide
• Synonyms: N-[(1S,2R,3E)-2-Hydroxy-1-(hydroxymethyl)-3-heptadecen-1-yl]-6-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]hexanamide; N-[(7-Nitrobenz-2-oxa-1,3-diazol-4-yl)aminocaproyl]sphingosine; NBD-C 6Cer; N-(NBD-Aminohexanoyl) D-erythro-Sphingosine; N-([7-Nitrobenz-2-oxa-1,3-diazol-4-yl]aminocaproyl)sphingosine; NBD hexanoic ceramide; N-(NBD-Aminohexanoyl)sphingosine

Database IDs

• CAS Number: 86701-10-2; 94885-02-6
• MDL Number: MFCD00467024
• PubChem SID: 24897860; 162227009
• PubChem CID: 16219783

CALCULATED PROPERTIES

• Acid pKa: 12.635408
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): 6.2375965
• LogD (pH = 7.4): 6.2375975
• Log P: 6.237598
• Molar Refractivity: 163.0864 cm^3
• Polarizability: 62.3988 Å^3
• Polar Surface Area: 166.33 Å^2
• Rotatable Bonds: 24
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Ethanol; Methanol
• Apperance: Redish Brown Solid
• Melting Point: >50°C (dec.)

Safety Information

• Storage Condition: Amber Vial, -20°C Freezer, Under Inert Atmosphere
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)
• Storage Temperature: -20°C

DETAILS

Toronto Research Chemicals - N381250

A vital fluoresent stain for the Golgi apparatus.

REFERENCES

• Putz, U., et al.: Eur. J. Cell Biol., 68, 113 (1995)