(2Z,4R,5S)-6-(hexadecanoyloxy)-2,3,4,5-tetrahydroxyhex-2-enoic acid

• ChemBase ID: 6051
• Molecular Formular: C22H40O8
• Molecular Mass: 432.5482
• Monoisotopic Mass: 432.27231824
• SMILES: C(=O)(CCCCCCCCCCCCCCC)OC[C@@H]([C@H](/C(=C(\C(=O)O)/O)/O)O)O
• Canonical SMILES: CCCCCCCCCCCCCCCC(=O)OC[C@@H]([C@H](/C(=C(\C(=O)O)/O)/O)O)O
• InChI: InChI=1S/C22H40O8/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(24)30-16-17(23)19(25)20(26)21(27)22(28)29/h17,19,23,25-27H,2-16H2,1H3,(H,28,29)/b21-20-/t17-,19+/m0/s1
• InChIKey: XWTWKBKNEMLBKW-KCWNHAIFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2Z,4R,5S)-6-(hexadecanoyloxy)-2,3,4,5-tetrahydroxyhex-2-enoic acid
• IUPAC Traditional name: (2Z,4R,5S)-6-(hexadecanoyloxy)-2,3,4,5-tetrahydroxyhex-2-enoic acid
• Synonyms: (2E,4R,5S)-2,3,4,5-TETRAHYDROXY-6-(PALMITOYLOXY)HEX-2-ENOIC ACID

Database IDs

• PubChem SID: 160969476; 99444909
• PubChem CID: 46937151; 54736482

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.034597
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): 1.6367133
• LogD (pH = 7.4): -0.3187723
• Log P: 4.1096907
• Molar Refractivity: 114.1157 cm^3
• Polarizability: 44.841732 Å^3
• Polar Surface Area: 144.52 Å^2
• Rotatable Bonds: 20
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 4.39
• LOG S: -4.57
• Solubility (Water): 1.18e-02 g/l

DETAILS

DrugBank - DB08438

Drug information: experimental