(5S,6R,7E,9E,11Z,14Z)-6-{[(2R)-2-amino-2-carboxyethyl]sulfanyl}-5-hydroxyicosa-7,9,11,14-tetraenoic acid

• ChemBase ID: 172202
• Molecular Formular: C23H37NO5S
• Molecular Mass: 439.60858
• Monoisotopic Mass: 439.23924429
• SMILES: C(=C\C/C=C\CCCCC)\C=C\C=C\[C@H]([C@H](CCCC(=O)O)O)SC[C@H](N)C(=O)O
• Canonical SMILES: CCCCC/C=C\C/C=C\C=C\C=C\[C@H]([C@H](CCCC(=O)O)O)SC[C@@H](C(=O)O)N
• InChI: InChI=1S/C23H37NO5S/c1-2-3-4-5-6-7-8-9-10-11-12-13-16-21(30-18-19(24)23(28)29)20(25)15-14-17-22(26)27/h6-7,9-13,16,19-21,25H,2-5,8,14-15,17-18,24H2,1H3,(H,26,27)(H,28,29)/b7-6-,10-9-,12-11+,16-13+/t19-,20-,21+/m0/s1
• InChIKey: OTZRAYGBFWZKMX-FRFVZSDQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5S,6R,7E,9E,11Z,14Z)-6-{[(2R)-2-amino-2-carboxyethyl]sulfanyl}-5-hydroxyicosa-7,9,11,14-tetraenoic acid
• IUPAC Traditional name: leukotriene E4
• Synonyms: (5S,6R,7E,9E,11Z,14Z)-6-[[(2R)-2-Amino-2-carboxyethyl]thio]-5-hydroxy-7,9,11,14-eicosatetraenoic Acid; LTE4; Leukotriene E; Leukotriene E4

Database IDs

• CAS Number: 75715-89-8
• PubChem SID: 164228112
• PubChem CID: 5280879

CALCULATED PROPERTIES

• Acid pKa: 2.38513
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): 1.0298574
• LogD (pH = 7.4): -0.7417159
• Log P: 2.0210793
• Molar Refractivity: 127.6197 cm^3
• Polarizability: 48.359455 Å^3
• Polar Surface Area: 120.85 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - L330350

A metabolite of Arachidonic acid (A765000) via the lipoxygenase pathway, chemically related to the prostaglandins and thromboxanes. The name leukotrienes was applied because of their origin in leukocytes and their conjugated triene structures.

REFERENCES

• Borgeat, P., et al.: J. Med. Chem., 24, 121 (1981)
• Kan, K., et al.: Eur. J. Pharmacol., 544, 153 (1981)
• Sam, T., et al.: J. Pharmacol. Sci., 103, 189 (1981)
• Darmani, N., et al.: Brain Res., 1248, 40 (1981)