20-Carboxy-leukotriene B4 (BioDeep_00000006012)
Main id: BioDeep_00000629577
human metabolite Endogenous blood metabolite
代谢物信息卡片
化学式: C20H30O6 (366.204228)
中文名称: 20-羧基白三烯B4
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: C(/C=C\C[C@H](/C=C/C=C/C=C\[C@H](CCCC(=O)O)O)O)CCCC(=O)O
InChI: InChI=1S/C20H30O6/c21-17(11-6-2-1-3-9-15-19(23)24)12-7-4-5-8-13-18(22)14-10-16-20(25)26/h2,4-8,12-13,17-18,21-22H,1,3,9-11,14-16H2,(H,23,24)(H,25,26)/b5-4+,6-2-,12-7+,13-8-/t17-,18-/m1/s1
描述信息
20-Carboxyleukotriene B4 is an omega-oxidized metabolite of leukotriene B4 (LTB4). Neutrophil microsomes are known to oxidize 20-hydroxy-LTB4 (20-OH-LTB4) to its 20-oxo and 20-carboxy derivatives in the presence of NADPH. This activity has been ascribed to LTB4 omega-hydroxylase (cytochrome P-450LTB omega). Leukotriene B4 release from polymorphonuclear granulocytes of severely burned patients was reduced as compared to healthy donor cells. This decrease is due to an enhanced conversion of LTB4 into the 20-hydroxy- and 20-carboxy-metabolites and further to a decreased LTB4-synthesis. LTB4 is the major metabolite in neutrophil polymorphonuclear leukocytes. Leukotrienes are metabolites of arachidonic acid derived from the action of 5-LO (5-lipoxygenase). The immediate product of 5-LO is LTA4 (leukotriene A4), which is enzymatically converted into either LTB4 (leukotriene B4) by LTA4 hydrolase or LTC4 (leukotriene C4) by LTC4 synthase. The regulation of leukotriene production occurs at various levels, including expression of 5-LO, translocation of 5-LO to the perinuclear region and phosphorylation to either enhance or inhibit the activity of 5-LO. Biologically active LTB4 is metabolized by w-oxidation carried out by specific cytochrome P450s (CYP4F) followed by beta-oxidation from the w-carboxy position and after CoA ester formation. Other specific pathways of leukotriene metabolism include the 12-hydroxydehydrogenase/ 15-oxo-prostaglandin-13-reductase that form a series of conjugated diene metabolites that have been observed to be excreted into human urine. Metabolism of LTC4 occurs by sequential peptide cleavage reactions involving a gamma-glutamyl transpeptidase that forms LTD4 (leukotriene D4) and a membrane-bound dipeptidase that converts LTD4 into LTE4 (leukotriene E4) before w-oxidation. These metabolic transformations of the primary leukotrienes are critical for termination of their biological activity, and defects in expression of participating enzymes may be involved in specific genetic disease. (PMID 17623009, 7633595, 2155225, 3039534)Leukotrienes are eicosanoids. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs), and lipoxins (LXs). The PGs and TXs are collectively identified as prostanoids. Prostaglandins were originally shown to be synthesized in the prostate gland, thromboxanes from platelets (thrombocytes), and leukotrienes from leukocytes, hence the derivation of their names. All mammalian cells except erythrocytes synthesize eicosanoids. These molecules are extremely potent, able to cause profound physiological effects at very dilute concentrations. All eicosanoids function locally at the site of synthesis, through receptor-mediated G-protein linked signalling pathways.
同义名列表
22 个代谢物同义名
(5S,6Z,8E,10E,12R,14Z)-5,12-Dihydroxyicosa-6,8,10,14-tetraenedioic acid; (S-(R*,s*-(e,Z,e,Z)))-5,12-dihydroxy-6,8,10,14-eicosatetraenedioic acid; (S-(R*,s*-(e,Z,e,Z)))-5,12-dihydroxy-6,8,10,14-eicosatetraenedioate; (5S,6Z,8E,10E,12R,14Z)-5,12-Dihydroxyicosa-6,8,10,14-tetraenedioate; 5(S),12(R)-Dihydroxy-20-carboxy-6,8,10,14-eicosatetraenoic acid; 5S,12R-dihydroxy-6Z,8E,10E,14Z-eicosatetraene-1,20-dioic acid; 5(S),12(R)-Dihydroxy-20-carboxy-6,8,10,14-eicosatetraenoate; 5S,12R-Dihydroxy-6Z,8E,10E,14Z-eicosatetraene-1,20-dioate; 5,12-Dihydroxy-delta5,8,11,14-eicosapolyendioic acid; 5,12-Dihydroxy-delta5,8,11,14-eicosapolyendioate; 5,12-Dihydroxy-δ5,8,11,14-eicosapolyendioic acid; 5,12-Dihydroxy-δ5,8,11,14-eicosapolyendioate; 20-Hydroxy-20-oxo-leukotriene b4; 20-hydroxy-20-oxoleukotriene B4; 20-Carboxy-leukotriene- b4; 20-carboxy-Leukotriene B4; 20-Carboxyleukotriene b4; 20-COOH-Leukotriene b4; 20-carboxy-LTB4; 20-COOH LTB4; 20-COOH-LTB4; DB-056434
数据库引用编号
16 个数据库交叉引用编号
- ChEBI: CHEBI:27562
- KEGG: C05950
- PubChem: 5280877
- PubChem: 1588
- HMDB: HMDB0006059
- Metlin: METLIN36247
- ChEMBL: CHEMBL1592630
- foodb: FDB112228
- chemspider: 4444400
- CAS: 80434-82-8
- PMhub: MS000018934
- PubChem: 8234
- LipidMAPS: LMFA03020016
- 3DMET: B01924
- NIKKAJI: J2.760.808F
- RefMet: 20-Carboxy-LTB4
分类词条
相关代谢途径
BioCyc(0)
PlantCyc(0)
代谢反应
104 个相关的代谢反应过程信息。
Reactome(55)
- Metabolism:
2MACA-CoA + CoA ⟶ Ac-CoA + PROP-CoA
- Metabolism of lipids:
H+ + LTHSOL + Oxygen + TPNH ⟶ 7-dehydroCHOL + H2O + TPN
- Fatty acid metabolism:
Ac-CoA + H2O ⟶ CH3COO- + CoA-SH
- Arachidonic acid metabolism:
H2O + leukotriene A4 ⟶ leukotriene B4
- Synthesis of Leukotrienes (LT) and Eoxins (EX):
H2O + leukotriene A4 ⟶ leukotriene B4
- Metabolism:
3alpha,7alpha,12alpha-trihydroxy-5beta-cholest-24-one-CoA + CoA-SH ⟶ choloyl-CoA + propionyl CoA
- Metabolism of lipids:
3alpha,7alpha,12alpha-trihydroxy-5beta-cholest-24-one-CoA + CoA-SH ⟶ choloyl-CoA + propionyl CoA
- Fatty acid metabolism:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA
- Arachidonic acid metabolism:
H+ + e- + prostaglandin G2 ⟶ H2O + prostaglandin H2
- Synthesis of Leukotrienes (LT) and Eoxins (EX):
H2O + leukotriene C4 ⟶ L-Glu + leukotriene D4
- Metabolism:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA
- Metabolism of lipids:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA
- Fatty acid metabolism:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA
- Arachidonic acid metabolism:
H+ + e- + prostaglandin G2 ⟶ H2O + prostaglandin H2
- Synthesis of Leukotrienes (LT) and Eoxins (EX):
H2O + leukotriene A4 ⟶ leukotriene B4
- Metabolism:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA
- Metabolism of lipids:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA
- Fatty acid metabolism:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA
- Arachidonic acid metabolism:
H+ + e- + prostaglandin G2 ⟶ H2O + prostaglandin H2
- Synthesis of Leukotrienes (LT) and Eoxins (EX):
H2O + leukotriene A4 ⟶ leukotriene B4
- Metabolism:
3alpha,7alpha,12alpha-trihydroxy-5beta-cholest-24-one-CoA + CoA-SH ⟶ choloyl-CoA + propionyl CoA
- Metabolism of lipids:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA
- Fatty acid metabolism:
ATP + PROP-CoA + carbon dioxide ⟶ ADP + MEMA-CoA + Pi
- Arachidonic acid metabolism:
H+ + e- + prostaglandin G2 ⟶ H2O + prostaglandin H2
- Synthesis of Leukotrienes (LT) and Eoxins (EX):
H2O + leukotriene A4 ⟶ leukotriene B4
- Metabolism:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA
- Metabolism of lipids:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA
- Fatty acid metabolism:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA
- Arachidonic acid metabolism:
H+ + e- + prostaglandin G2 ⟶ H2O + prostaglandin H2
- Synthesis of Leukotrienes (LT) and Eoxins (EX):
H2O + leukotriene A4 ⟶ leukotriene B4
- Metabolism:
2MACA-CoA + CoA ⟶ Ac-CoA + PROP-CoA
- Metabolism of lipids:
H+ + LTHSOL + Oxygen + TPNH ⟶ 7-dehydroCHOL + H2O + TPN
- Fatty acid metabolism:
Ac-CoA + H2O ⟶ CH3COO- + CoA-SH
- Arachidonic acid metabolism:
H2O + leukotriene A4 ⟶ leukotriene B4
- Synthesis of Leukotrienes (LT) and Eoxins (EX):
H2O + leukotriene A4 ⟶ leukotriene B4
- Metabolism:
2MACA-CoA + CoA ⟶ Ac-CoA + PROP-CoA
- Metabolism of lipids:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA
- Fatty acid metabolism:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA
- Arachidonic acid metabolism:
H+ + e- + prostaglandin G2 ⟶ H2O + prostaglandin H2
- Synthesis of Leukotrienes (LT) and Eoxins (EX):
H2O + leukotriene A4 ⟶ leukotriene B4
- Metabolism:
ATP + PROP-CoA + carbon dioxide ⟶ ADP + MEMA-CoA + Pi
- Metabolism of lipids:
ATP + PROP-CoA + carbon dioxide ⟶ ADP + MEMA-CoA + Pi
- Fatty acid metabolism:
ATP + PROP-CoA + carbon dioxide ⟶ ADP + MEMA-CoA + Pi
- Arachidonic acid metabolism:
H+ + e- + prostaglandin G2 ⟶ H2O + prostaglandin H2
- Synthesis of Leukotrienes (LT) and Eoxins (EX):
H2O + leukotriene A4 ⟶ leukotriene B4
- Metabolism:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA
- Metabolism of lipids:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA
- Fatty acid metabolism:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA
- Arachidonic acid metabolism:
H+ + e- + prostaglandin G2 ⟶ H2O + prostaglandin H2
- Synthesis of Leukotrienes (LT) and Eoxins (EX):
GSH + leukotriene A4 ⟶ leukotriene C4
- Metabolism:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA
- Metabolism of lipids:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA
- Fatty acid metabolism:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA
- Arachidonic acid metabolism:
H+ + e- + prostaglandin G2 ⟶ H2O + prostaglandin H2
- Synthesis of Leukotrienes (LT) and Eoxins (EX):
H2O + leukotriene A4 ⟶ leukotriene B4
BioCyc(0)
WikiPathways(3)
- Eicosanoid metabolism via lipoxygenases (LOX):
Arachidonic acid ⟶ 12-HETE
- Leukotriene metabolic pathway:
16-COOH-tetranor-LTE3 ⟶ 14-COOH-hexanor-LTE4
- Arachidonic acid (AA, ARA) oxylipin metabolism:
HXB3 ⟶ Trioxilin B3
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(46)
- Arachidonic Acid Metabolism:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Leukotriene C4 Synthesis Deficiency:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Piroxicam Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Acetylsalicylic Acid Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Etodolac Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Ketoprofen Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Ibuprofen Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Rofecoxib Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Diclofenac Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Sulindac Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Celecoxib Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Ketorolac Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Suprofen Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Bromfenac Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Indomethacin Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Mefenamic Acid Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Oxaprozin Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Nabumetone Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Naproxen Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Diflunisal Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Meloxicam Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Valdecoxib Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Antipyrine Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Antrafenine Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Carprofen Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Etoricoxib Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Fenoprofen Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Flurbiprofen Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Magnesium Salicylate Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Lumiracoxib Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Lornoxicam Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Phenylbutazone Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Nepafenac Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Trisalicylate-Choline Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Tolmetin Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Tiaprofenic Acid Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Tenoxicam Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Salsalate Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Salicylate-Sodium Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Salicylic Acid Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Acetaminophen Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Arachidonic Acid Metabolism:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Leukotriene C4 Synthesis Deficiency:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Arachidonic Acid Metabolism:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Arachidonic Acid Metabolism:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Leukotriene C4 Synthesis Deficiency:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
PharmGKB(0)
2 个相关的物种来源信息
- 9606 - Homo sapiens: -
- 9606 - Homo sapiens: 10.1007/S11306-016-1051-4
在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有:
- PubMed: 来源于PubMed文献库中的文献信息,我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表,这个列表按照代谢物同时出现的文献数量降序排序,取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
- NCBI Taxonomy: 通过文献数据挖掘,得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序,取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
- Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
- Chemical Reaction: 在化学反应过程中,存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。
点击图上的相关代谢物的名称,可以跳转到相关代谢物的信息页面。
文献列表
- M A Willemsen, J J Rotteveel, J G de Jong, R J Wanders, L IJlst, G F Hoffmann, E Mayatepek. Defective metabolism of leukotriene B4 in the Sjögren-Larsson syndrome.
Journal of the neurological sciences.
2001 Jan; 183(1):61-7. doi:
10.1016/s0022-510x(00)00474-3
. [PMID: 11166796] - J P Merab, S J Feinmark, P J Cannon. Synthesis of leukotrienes C4, D4, E4 and 20-carboxy-B4 by the isolated perfused kidney.
Advances in prostaglandin, thromboxane, and leukotriene research.
1989; 19(?):221-4. doi:
NULL
. [PMID: 2546385]