N-[(4E)-3-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}octadec-4-en-2-yl]-12-[(2,4,6-trinitrophenyl)amino]dodecanamide

• ChemBase ID: 131868
• Molecular Formular: C42H71N5O14
• Molecular Mass: 870.03824
• Monoisotopic Mass: 869.49975198
• SMILES: CCCCCCCCCCCCC/C=C/C(C(COC1C(C(C(C(O1)CO)O)O)O)NC(=O)CCCCCCCCCCCNc1c(cc(cc1[N+](=O)[O-])[N+](=O)[O-])[N+](=O)[O-])O
• Canonical SMILES: CCCCCCCCCCCCC/C=C/C(C(NC(=O)CCCCCCCCCCCNc1c(cc(cc1[N+](=O)[O-])[N+](=O)[O-])[N+](=O)[O-])COC1OC(CO)C(C(C1O)O)O)O
• InChI: InChI=1S/C42H71N5O14/c1-2-3-4-5-6-7-8-9-10-12-15-18-21-24-35(49)32(30-60-42-41(53)40(52)39(51)36(29-48)61-42)44-37(50)25-22-19-16-13-11-14-17-20-23-26-43-38-33(46(56)57)27-31(45(54)55)28-34(38)47(58)59/h21,24,27-28,32,35-36,39-43,48-49,51-53H,2-20,22-23,25-26,29-30H2,1H3,(H,44,50)/b24-21+
• InChIKey: CKSSCTIRJIGIPC-DARPEHSRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(4E)-3-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}octadec-4-en-2-yl]-12-[(2,4,6-trinitrophenyl)amino]dodecanamide
• IUPAC Traditional name: N-[(4E)-3-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}octadec-4-en-2-yl]-12-[(2,4,6-trinitrophenyl)amino]dodecanamide
• Synonyms: Trinitrophenylaminolauroylgalactocerebroside; TNPAL-galactocerebroside; Trinitrophenylaminolauroylglucocerebroside; TNPAL-glucocerebroside

Database IDs

• CAS Number: 118099-48-2; 117961-26-9
• MDL Number: MFCD01090954; MFCD01090955
• PubChem SID: 162226145; 24899911
• PubChem CID: 6391434

CALCULATED PROPERTIES

• Acid pKa: 10.019284
• H Acceptors: 15
• H Donor: 7
• LogD (pH = 5.5): 8.314106
• LogD (pH = 7.4): 8.313129
• Log P: 8.314119
• Molar Refractivity: 231.6783 cm^3
• Polarizability: 88.27176 Å^3
• Polar Surface Area: 298.2 Å^2
• Rotatable Bonds: 35
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Storage Temperature: -20°C

DETAILS

Sigma Aldrich - T1139

Preparation Note
Prepared from glucocerebrosides from Human (Gaucher′s) Spleen