CAS 75715-89-8 Leukotriene E4 (HCID 5280879)

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Basic information

CAS: 75715-89-8
Standard SMILES: CCCCC/C=C\C\C=C/C=C/C=C/[C@@H](SC[C@H](N)C(=O)O)[C@@H](O)CCCC(=O)O
InChIKey: OTZRAYGBFWZKMX-FRFVZSDQSA-N
Molecular formula: C23H37NO5S
Average molar mass: 439.6 g/mol
Monoisotopic mass: 439.23924428

Overview

Leukotriene E4 is a leukotriene that is (7E,9E,11Z,14Z)-icosa-7,9,11,14-tetraenoic acid substituted by a hydroxy group at position 5 (5S) and an L-cystein-S-yl group at position 6 (6R). It is a leukotriene, a L-cysteine thioether, a secondary alcohol, an amino dicarboxylic acid and a non-proteinogenic L-alpha-amino acid. It is functionally related to an icosa-7,9,11,14-tetraenoic acid. It is a conjugate acid of a leukotriene E4(1-).

Names & identifiers

Preferred name: Leukotriene E4
IUPAC: (5S,6R,7E,9E,11Z,14Z)-6-[(2R)-2-amino-2-carboxyethyl]sulfanyl-5-hydroxyicosa-7,9,11,14-tetraenoic acid
English name: Leukotriene E4
Molecular formula: C23H37NO5S
Molecular weight: 439.61

Names & synonyms

leukotriene E4LTE475715-89-8Leukotriene E8EYT8ATL7GCHEBI:15650DTXSID208975105S-hydroxy,6R-(S-cysteinyl),7E,9E,11Z,14Z-eicosatetraenoic acid(5S,6R,7E,9E,11Z,14Z)-6-[(2R)-2-amino-2-carboxyethyl]sulfanyl-5-hydroxyicosa-7,9,11,14-tetraenoic acid(7E,9E,11Z,14Z)-(5S,6R)-6-(Cystein-S-yl)-5-hydroxyeicosa-7,9,11,14-tetraenoate(7E,9E,11Z,14Z)-(5S,6R)-6-(Cystein-S-yl)-5-hydroxyicosa-7,9,11,14-tetraenoate(5S-(5R*,6S*(S*),7E,9E,11Z,14Z))-6-((2-Amino-2-carboxyethyl)thio)-5-hydroxy-7,9,11,14-eicosatetraenoic acid

Show more names

Leukotriene E4 MaxSpecStandardLeukotriene E4 Lipid Maps MS StandardLeukotriene E4, CysLT1 and CysLT2 agonistLEUKOTRIENE E4 SOLUTION (100UG/ML ETHANOL)5S-HYDROXY-6R-(S-CYSTEINYL)-7E,9E,11Z,14Z-EICOSATETRAENOIC ACID(5S,6R,7E,9E,11Z,14Z)-6-(2-amino-3-hydroxy-3-oxopropyl)sulfanyl-5-hydroxyic(5S,6R,7E,9E,11Z,14Z)-6-[[(R)-2-Amino-2-carboxyethyl]thio]-5-hydroxy-7,9,11,14-icosatetraenoic acid

Properties

Computed structural properties

XLogP: 2.1
Topological polar surface area: 146 Å²
Hydrogen bond donors: 4
Hydrogen bond acceptors: 7
Rotatable bonds: 18
Heavy atoms: 30
Formal charge: 0
Complexity: 586

Experimental & physicochemical properties

LipidsFatty Acyls [FA] -> Eicosanoids [FA03] -> Leukotrienes [FA0302]

Physical DescriptionSolid

Collision Cross Section · 3 items

212.1 Å² [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Calculation: Single Field; Dataset: Oxylipins]

227.9 Å² [M+Na]+ [CCS Type: DT; Method: stepped-field]

213.2 Å² [M-H]-

Physicochemical properties

storage temp.: 20 °C · −20°C
solubility: 50 mg/mL · 50mg/mL in DMSO or in DMF
form: Liquid.
color: Colorless to light yellow
FDA UNII: 8 EYT8ATL7G · 8EYT8ATL7G
UNSPSC Code: 12352211 · 12352211
NACRES: 25 · NA.25
Symbol(GHS): 2 · GHS02,GHS07
Signal word: Danger

Safety & regulation

Safety data

wgk: WGK 1
ridadr: UN 1230 3/PG 2
risk_code: 11
Signal word: Danger
Symbol(GHS): GHS02,GHS07
hazard_code: F,T
safety_code: 7-16-23-45
Storage Class: 3 - Flammable liquids
Hazard statements: H225-H319
Hazard Classifications: Eye Irrit. 2Flam. Liq. 2
Precautionary statements: P210-P233-P240-P241-P242-P305+P351+P338

Chemistry & industry

Pharmacology

Tissue LocationsSmooth Muscle

Cellular LocationsCytoplasm

Metabolite PathwaysFc Epsilon Receptor I Signaling in Mast Cells

Applications · 1 item

UsesLeukotriene E4 is 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.

Suppliers23 total

陕西缔都医药有限责任公司029-81124775 17791530730 · [email protected]

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]

上海金试生化科技有限公司18601717983 18601717983 · [email protected]

上海钰博生物科技有限公司021-60514606 18321282235 · [email protected]

上海优宁维生物科技股份有限公司15921930842 15921930842 · [email protected]

Related reactions

1 records

New reaction record

HRID 741792As reactantuspto-grants-1996_09

Compound notes

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