N-[(2R,3R,4E)-1,3-dihydroxy(1,2-13C2,1,1-2H2)octadec-4-en-2-yl]nonadecanamide

• ChemBase ID: 175553
• Molecular Formular: C37H73NO3
• Molecular Mass: 581.96572968
• Monoisotopic Mass: 581.56575488
• SMILES: C(CCCCCCCCCCC/C=C/[C@H]([13C@H]([13CH2]O)NC(=O)CCCCCCCCCCCCCCCCCC)O)C
• Canonical SMILES: CCCCCCCCCCCCCCCCCCC(=O)N[13C@H]([C@@H](/C=C/CCCCCCCCCCCCC)O)[13CH2]O
• InChI: InChI=1S/C37H73NO3/c1-3-5-7-9-11-13-15-17-18-19-21-23-25-27-29-31-33-37(41)38-35(34-39)36(40)32-30-28-26-24-22-20-16-14-12-10-8-6-4-2/h30,32,35-36,39-40H,3-29,31,33-34H2,1-2H3,(H,38,41)/b32-30+/t35-,36+/m0/s1/i34+1,35+1
• InChIKey: SNMLDULQFHAZRC-HTJWJNQOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2R,3R,4E)-1,3-dihydroxy(1,2-^1^3C₂,1,1-^2H₂)octadec-4-en-2-yl]nonadecanamide
• IUPAC Traditional name: N-[(2R,3R,4E)-1,3-dihydroxy(1,2-^1^3C₂,1,1-^2H₂)octadec-4-en-2-yl]nonadecanamide
• Synonyms: N-[(1S,2R,3E)-2-Hydroxy-1-(hydroxymethyl)-3-heptadecen-1-yl]nonadecanamide-13C2,d2; N-Nonadecanoyl-D-erythro-sphingosine-13C2,d2

Database IDs

• PubChem SID: 164231463
• PubChem CID: 71751156

CALCULATED PROPERTIES

• Acid pKa: 13.619749
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 12.1990595
• LogD (pH = 7.4): 12.19906
• Log P: 12.199061
• Molar Refractivity: 179.5787 cm^3
• Polarizability: 71.12878 Å^3
• Polar Surface Area: 69.56 Å^2
• Rotatable Bonds: 33
• Lipinski's Rule of Five: false

REFERENCES

• Krishna, N., et al.: Nat. Prod. Res., 18, 551 (2004)