Structure Database (LMSD)

Common Name
N-acetyl-LTE4
Systematic Name
5S-hydroxy-6R-(S-(N-acetylcysteinyl))-7E,9E,11Z,14Z-eicosatetraenoic acid
Synonyms
  • N-acetyl-Leukotriene E4
LM ID
LMFA03020008
Formula
C25H39NO6S
Exact Mass
Calculate m/z
481.24981
Status
Curated
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Eicosanoids [FA03]
Leukotrienes [FA0302]
Fatty Acids and Conjugates [FA01]
Unsaturated fatty acids [FA0103]
Hydroxy fatty acids [FA0105]

Biological Context

N-acetyl LTE4 is the major inactive metabolite of LTE4 found in bile. This route of metabolism is prominent in the rat, but of minor importance in humans.1,2 N-acetyl LTE4 is 100 times less potent than LTC4 as a vasoconstricting agent.2 In healthy human subjects urinary excretion of N-acetyl LTE4 is about 1.5 nmol/mol creatinine, which is considerably less than that of LTE4 (12 nmol/mol creatinine).3

This information has been provided by Cayman Chemical

References

1. Huber, M., Müller, J., Leier, I., et al. Metabolism of cysteinyl leukotrienes in monkey and man. Eur. J. Biochem. 194, 309-315 (1990).
1. Denzlinger, C., Rapp, S., Hagmann, W., et al. Leukotrienes as mediators in tissue trauma. Science 230, 330-332 (1985).
2. Denzlinger, C., Rapp, S., Hagmann, W., et al. Leukotrienes as mediators in tissue trauma. Science 230, 330-332 (1985).
2. Foster, A., Fitzsimmons, B., and Letts, L.G. The synthesis of N-acetyl-leukotriene E4 and its effects on cardiovascular and respiratory function of the anesthetized pig. Prostaglandins 31, 1077-1086 (1986).
2. Foster, A., Fitzsimmons, B., and Letts, L.G. The synthesis of N-acetyl-leukotriene E4 and its effects on cardiovascular and respiratory function of the anesthetized pig. Prostaglandins 31, 1077-1086 (1986).
3. Foster, A., Fitzsimmons, B., and Letts, L.G. The synthesis of N-acetyl-leukotriene E4 and its effects on cardiovascular and respiratory function of the anesthetized pig. Prostaglandins 31, 1077-1086 (1986).
3. Huber, M., Müller, J., Leier, I., et al. Metabolism of cysteinyl leukotrienes in monkey and man. Eur. J. Biochem. 194, 309-315 (1990).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Rattus norvegicus (#10116)
Mammalia (#40674)
Metabolism of leukotrienes.,
Mol Cell Biochem, 1985
Pubmed ID: 3001504

String Representations

InChiKey (Click to copy)
BGGYAYMMFYBWEX-HXDOPMNESA-N
InChi (Click to copy)
InChI=1S/C25H39NO6S/c1-3-4-5-6-7-8-9-10-11-12-13-14-17-23(22(28)16-15-18-24(29)30)33-19-21(25(31)32)26-20(2)27/h7-8,10-14,17,21-23,28H,3-6,9,15-16,18-19H2,1-2H3,(H,26,27)(H,29,30)(H,31,32)/b8-7-,11-10-,13-12+,17-14+/t21-,22-,23+/m0/s1
SMILES (Click to copy)
C(/C/C=C\CCCCC)=C/C=C/C=C/[C@@H](SC[C@H](NC(=O)C)C(=O)O)[C@@H](O)CCCC(O)=O

Other Databases

LIPIDBANK ID
XPR3411
PubChem CID
5283123
Cayman ID
20420

Calculated Physicochemical Properties

Heavy Atoms 33
Rings 0
Aromatic Rings 0
Rotatable Bonds 19
Van der Waals Molecular Volume 504.83
Topological Polar Surface Area 123.93
Hydrogen Bond Donors 4
Hydrogen Bond Acceptors 7
logP 5.63
Molar Refractivity 136.33

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Created at
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Updated at
7th Jan 2022