(5S,12R,6Z,8E,10E,14Z)-5,12-ジヒドロキシ-6,8,10,14-イコサテトラエン酸

Leukotriene B4

HCID 5280492

基本情報

CAS: 71160-24-2
標準SMILES: CCCCC/C=C\C[C@@H](O)/C=C/C=C/C=C\[C@@H](O)CCCC(=O)O
InChIKey: VNYSSYRCGWBHLG-AMOLWHMGSA-N
分子式: C20H32O4
平均分子量: 336.5 g/mol
単同位体質量: 336.2300595

概要

Leukotriene B4 is a leukotriene composed of (6Z,8E,10E,14Z)-icosatetraenoic acid having (5S)- and (12R)-hydroxy substituents. It is a lipid mediator of inflammation that is generated from arachidonic acid via the 5-lipoxygenase pathway. It has a role as a vasoconstrictor agent, a mouse metabolite, a plant metabolite and a human metabolite. It is a hydroxy polyunsaturated fatty acid, a long-chain fatty acid, a leukotriene and a dihydroxy monocarboxylic acid. It is functionally related to an icosa-6,8,10,14-tetraenoic acid. It is a conjugate acid of a leukotriene B4(1-).

名称と識別子

優先名称: Leukotriene B4
IUPAC: (5S,6Z,8E,10E,12R,14Z)-5,12-dihydroxyicosa-6,8,10,14-tetraenoic acid
現地名: (5S,12R,6Z,8E,10E,14Z)-5,12-ジヒドロキシ-6,8,10,14-イコサテトラエン酸
英語名: Leukotriene B4
分子式: C20H32O4
分子量: 336.47

名称と別名

LEUKOTRIENE B4LTB471160-24-25,12-Hete(5S,6Z,8E,10E,12R,14Z)-5,12-dihydroxyicosa-6,8,10,14-tetraenoic acidLEUKOTRIENE_B41HGW4DR56D5S,12R-dihydroxy-6Z,8E,10E,14Z-eicosatetraenoic acid5S,12R-diHETEDTXSID4037162CHEBI:15647(6z,8e,10e,14z)-(5s,12r)-5,12-dihydroxyicosa-6,8,10,14-tetraenoate

名称をさらに表示

(5S,6Z,8E,10E,12R,14Z)-5,12-ジヒドロキシ-6,8,10,14-イコサテトラエン酸(5S,6Z,8E,10E,12R,14Z)-5,12-ジヒドロキシイコサ-6,8,10,14-テトラエン酸ロイコトリエンB4(5S,12R,6Z,8E,10E,14Z)-5,12-ジヒドロキシ-6,8,10,14-イコサテトラエン酸ロイコトリエンB4 (エタノール溶液)Leukotriene B?LTB4 (Leukotriene B4)VNYSSYRCGWBHLG-AMOLWHMGSA-NLeukotriene B4 MaxSpecStandardleukotriene B4 ethanol solutionLeukotriene B4 Lipid Maps MS StandardLeukotriene B - CAS 71160-24-2 - Calbiochem

Leukotriene B5,12 diHETELeukotriene B 4Leukotriene B-4B-4, LeukotrieneRefChem:1531495,12 HETEDTXCID401765891

データベース識別子

CAS: 71160-24-2
PubChem CID: 5280492
DTXSID: DTXSID4037162
ChEMBL: CHEMBL65061
ChEBI: CHEBI:15647
UNII: 1HGW4DR56D
Nikkaji: J240.041C

物性

構造計算による物性

XLogP: 4.1
極性表面積: 77.8 Å²
水素結合供与体数: 3
水素結合受容体数: 4
回転可能結合数: 14
重原子数: 24
形式電荷: 0
複雑度: 421

実験および物理化学的性質

Chemical ClassesOther Uses -> Biochemical Research

DrugsPharmaceuticals -> Listed in ZINC15

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

Physical Description · 2 件

Colorless liquid; [Fisher Scientific MSDS]

Solid

Collision Cross Section · 3 件

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

187.44 Å² [M-H]- [CCS Type: DT; Method: stepped-field]

186.8 Å² [M-H]-

物理化学的性質

沸点: 536.4 · 536.4±50.0 °C(Predicted)
比重(密度): 1.04 · 1.040±0.06 g/cm3(Predicted)
闪点: 14 °C · 14 °C
貯蔵温度: -20 °C · -20°C
溶解性: Soluble in ethanol (supplied pre-dissolved in anhydrous ethanol, 50μg/ml)
外見: クリアオイル
酸解離定数(Pka): 4.66 · 4.66±0.10(Predicted)
色: Colorless to light yellow
InChIKey: VNYSSYRCGWBHLG-AMOLWHMGSA-N
SMILES: CCCCC\C=C/C[C@@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O
CAS データベース: 71160 · 71160-24-2(CAS DataBase Reference)

安全と法規制

危険有害性情報

Hazards SummaryAn irritant; Inhalation of high concentrations may cause bronchospasm and delayed pulmonary edema; [Fisher Scientific MSDS]

毒性情報

Adverse EffectsToxic Pneumonitis - Inflammation of the lungs induced by inhalation of metal fumes or toxic gases and vapors.

安全データ

wgk: 1
ridadr: UN 1170 3/PG 2
risk_code: 11
hazard_code: F
safety_code: 7-16
Hazard Classifications: Eye Irrit. 2Flam. Liq. 2
ストレージクラス: 3 - Flammable liquids

化学と産業

薬理情報

Tissue LocationsEpidermis

Cellular LocationsCytoplasm

Metabolite PathwaysAcetaminophen Action Pathway

用途と製造

Uses · 1 件

Leukotrienes are metabolites of arachidonic acid that are chemically related to prostaglandins and thromboxanes; They are potent bronchoconstrictors that serve an important role in immediate hypersensitivity reactions; [Merck Index] The major metabolite in neutrophil polymorphonuclear leukocytes. It stimulates polymorphonuclear cell function (degranulation, formation of oxygen-centered free radicals, arachidonic acid release, and metabolism). (From Dictionary of Prostaglandins and Related Compounds, 1990) [ChemIDplus]