FA 20:5;O3 (BioDeep_00000629501)
Secondary id: BioDeep_00000005626, BioDeep_00000005646, BioDeep_00000012129, BioDeep_00000019525, BioDeep_00000228716, BioDeep_00000558247, BioDeep_00001869356, BioDeep_00001869458
PANOMIX_OTCML-2023
代谢物信息卡片
化学式: C20H30O5 (350.2093)
中文名称:
谱图信息:
最多检出来源 Homo sapiens(blood) 12.82%
分子结构信息
SMILES: C(/C=C/C=C/[C@@H](O)[C@@H](O)CCCC(O)=O)=C/C=C/C(=O)CCCCC
InChI: InChI=1S/C20H30O5/c1-15(21)7-6-8-17(22)13-11-16-12-14-19(23)18(16)9-4-2-3-5-10-20(24)25/h2,4,11-18,21-22H,3,5-10H2,1H3,(H,24,25)/b4-2-,13-11+/t15-,16+,17+,18-/m1/s1
描述信息
同义名列表
46 个代谢物同义名
12-oxo-5S,18S-dihydroxy-6Z,8E,14Z,16E-eicosatetraenoic acid; 10,11-dihydro-12-oxo-Resolvin E1; 10,11-dihydro-12-oxo-RvE1; FA 20:5;O3; 9,15-dioxo-11R-hydroxy-5Z,13E-prostadienoic acid-cyclo[8S,12R]; 8-iso-15-keto-PGE2; 5,6,18-trihydroxy-7E,9E,11E,14Z,16Z-eicosapentaenoic acid; 5,6,18-triHEPE; 5,12,18-trihydroxy-6E,8E,10E,14Z,16Z-eicosapentaenoic acid; 6-trans-5,12,18-triHEPE; 5S-hydroperoxy-18S-hydroxy-6E,8Z,11Z,14Z,16E-eicosapentaenoic acid; 5S-Hp-18S-HEPE; 5S-hydroperoxy-18R-hydroxy-6E,8Z,11Z,14Z,16E-eicosapentaenoic acid; 5S-Hp-18R-HEPE; (5R,6R,7E,9E,11Z,13E)-5,6-dihydroxy-15-oxoicosa-7,9,11,13-tetraenoic acid; 15-Oxo-lipoxin A4; 15-oxo-5S,6R-dihydroxy-7E,9E,11Z,13E-eicosatetraenoic acid; 15-keto-Lipoxin A4; 15-keto-LXA4; 15-oxo-LXA4; (5S,6Z,8E,10E,12R,14Z)-5,12-dihydroxy-20-oxoicosa-6,8,10,14-tetraenoic acid; 20-oxo-leukotriene B4; (5R,6E,8Z,10E,12E,14R,15R,17Z)-5,14,15-trihydroxyicosa-6,8,10,12,17-pentaenoic acid; 15-Epi-lipoxin B5; (5R,6Z,8E,10E,14Z)-5,20-dihydroxy-12-oxoicosa-6,8,10,14-tetraenoic acid; 12-Oxo-20-hydroxy-leukotriene B4; (5Z,13E)-9alpha-Hydroxy-11,15-dioxoprosta-5,13-dienoate; 9S-hydroxy-11,15-dioxo-5Z,13E-prostadienoic acid; 15-deoxy-15-oxo-prostaglandin D2; 15-dehydro-prostaglandin D2; 15-keto-PGD2; 9-oxo-15S,19R-dihydroxy-5Z,8(12),13E-prostatrienoic acid; 19(R)-hydroxy-Prostaglandin B2; 19R-hydroxy-PGB2; 9-oxo-15S,19R-dihydroxy-5Z,10Z,13E-prostatrienoic acid; 19(R)-hydroxy-Prostaglandin A2; 19R-hydroxy-PGA2; 9-oxo-15S,19-dihydroxy-5Z,8(12),13E-prostatrienoic acid; 19-hydroxy-Prostaglandin B2; 19-hydroxy-PGB2; 9oxo-15S,19-dihydroxy-5Z,10Z,13E-prostatrienoic acid; 19-hydroxy-Prostaglandin A2; 19-hydroxy-PGA2; 9,15-dioxo-11R-hydroxy-5Z,13E-prostadienoic acid; 15-keto-Prostaglandin E2; 15-keto-PGE2
数据库引用编号
66 个数据库交叉引用编号
- ChEBI: CHEBI:165276
- ChEBI: CHEBI:172574
- ChEBI: CHEBI:165270
- ChEBI: CHEBI:165272
- ChEBI: CHEBI:132908
- ChEBI: CHEBI:81562
- ChEBI: CHEBI:63992
- ChEBI: CHEBI:63979
- ChEBI: CHEBI:175479
- ChEBI: CHEBI:15557
- ChEBI: CHEBI:165311
- ChEBI: CHEBI:165310
- ChEBI: CHEBI:140492
- ChEBI: CHEBI:192840
- ChEBI: CHEBI:15547
- KEGG: C18176
- KEGG: C04758
- KEGG: C04707
- PubChem: 53477458
- PubChem: 16061134
- PubChem: 52921897
- PubChem: 52921896
- PubChem: 46174067
- PubChem: 53481477
- PubChem: 52921886
- PubChem: 6449839
- PubChem: 53481476
- PubChem: 53481459
- PubChem: 5280727
- PubChem: 16061099
- PubChem: 16061098
- PubChem: 5283111
- PubChem: 5283110
- PubChem: 5280719
- ChEMBL: CHEMBL1447369
- LipidMAPS: LMFA03140002
- LipidMAPS: LMFA03110009
- LipidMAPS: LMFA03070042
- LipidMAPS: LMFA03070041
- LipidMAPS: LMFA03070039
- LipidMAPS: LMFA03070034
- LipidMAPS: LMFA03040011
- LipidMAPS: LMFA03040009
- LipidMAPS: LMFA03020064
- LipidMAPS: LMFA03020053
- LipidMAPS: LMFA03020049
- LipidMAPS: LMFA03010206
- LipidMAPS: LMFA03010167
- LipidMAPS: LMFA03010166
- LipidMAPS: LMFA03010132
- LipidMAPS: LMFA03010130
- LipidMAPS: LMFA03010030
- CAS: 914804-63-0
- CAS: 115609-68-2
- CAS: 52087-58-8
- CAS: 67392-20-5
- CAS: 26441-05-4
- PubChem: 7280
- NIKKAJI: J346.055J
- PubChem: 7326
- NIKKAJI: J2.753.567D
- PubChem: 96024392
- RefMet: 5S-Hp-18R-HEPE
- RefMet: 15-Keto-PGE2
- LOTUS: LTS0076428
- wikidata: Q27155467
分类词条
相关代谢途径
Reactome(7)
BioCyc(0)
PlantCyc(0)
代谢反应
45 个相关的代谢反应过程信息。
Reactome(44)
- 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 - Biosynthesis of specialized proresolving mediators (SPMs):
DHA + Oxygen ⟶ 17-HDHA - Synthesis of Lipoxins (LX):
NAD + lipoxin A4 ⟶ 15k-LXA4 + H+ + NADH - Synthesis of Lipoxins (LX):
NAD + lipoxin A4 ⟶ 15k-LXA4 + H+ + NADH - 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 - Biosynthesis of specialized proresolving mediators (SPMs):
13(S),14(S)-epoxy-DHA + GSH ⟶ (13R)-S-glutathionyl-(14S)-hydroxy-(4Z,7Z,9E,11E,16Z,19Z)-docosahexaenoic acid - Synthesis of Lipoxins (LX):
NAD + lipoxin A4 ⟶ 15k-LXA4 + H+ + NADH - 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 - Biosynthesis of specialized proresolving mediators (SPMs):
DHA + Oxygen ⟶ 17-HDHA - Synthesis of Lipoxins (LX):
NAD + lipoxin A4 ⟶ 15k-LXA4 + H+ + NADH - 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 - Biosynthesis of specialized proresolving mediators (SPMs):
DHA + Oxygen ⟶ 17-HDHA - Synthesis of Lipoxins (LX):
NAD + lipoxin A4 ⟶ 15k-LXA4 + H+ + NADH - 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 - Biosynthesis of specialized proresolving mediators (SPMs):
DHA + Oxygen ⟶ 17-HDHA - Synthesis of Lipoxins (LX):
NAD + lipoxin A4 ⟶ 15k-LXA4 + H+ + NADH - Metabolism:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA - Metabolism of lipids:
3-oxopristanoyl-CoA + CoA-SH ⟶ 4,8,12-trimethyltridecanoyl-CoA + propionyl CoA - Biosynthesis of specialized proresolving mediators (SPMs):
NAD + lipoxin A4 ⟶ 15k-LXA4 + H+ + NADH - Synthesis of Lipoxins (LX):
NAD + lipoxin A4 ⟶ 15k-LXA4 + H+ + NADH - Metabolism:
2MACA-CoA + CoA ⟶ Ac-CoA + PROP-CoA - Metabolism of lipids:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA - Biosynthesis of specialized proresolving mediators (SPMs):
18(R)-HpEPE + GSH ⟶ 18(R)-HEPE + GSSG + H2O - Synthesis of Lipoxins (LX):
NAD + lipoxin A4 ⟶ 15k-LXA4 + H+ + NADH - 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 - Biosynthesis of specialized proresolving mediators (SPMs):
DHA + Oxygen ⟶ 17-HDHA - Synthesis of Lipoxins (LX):
NAD + lipoxin A4 ⟶ 15k-LXA4 + H+ + NADH - Metabolism:
2MACA-CoA + CoA ⟶ Ac-CoA + PROP-CoA - Metabolism of lipids:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA - Biosynthesis of specialized proresolving mediators (SPMs):
DHA + Oxygen ⟶ 17-HDHA - Synthesis of Lipoxins (LX):
NAD + lipoxin A4 ⟶ 15k-LXA4 + H+ + NADH - Metabolism:
ATP + PROP-CoA + carbon dioxide ⟶ ADP + MEMA-CoA + Pi - Metabolism of lipids:
ATP + PROP-CoA + carbon dioxide ⟶ ADP + MEMA-CoA + Pi - Biosynthesis of specialized proresolving mediators (SPMs):
DHA + Oxygen ⟶ 17-HDHA - Synthesis of Lipoxins (LX):
NAD + lipoxin A4 ⟶ 15k-LXA4 + H+ + NADH - 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 - Biosynthesis of specialized proresolving mediators (SPMs):
DHA + Oxygen ⟶ 17-HDHA
BioCyc(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
4 个相关的物种来源信息
- 7461 - Apis cerana: 10.1371/JOURNAL.PONE.0175573
- 2777 - Gracilaria gracilis: 10.1016/S0031-9422(01)00321-1
- 172976 - Gracilariopsis longissima: 10.1016/S0031-9422(01)00321-1
- 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
- Eun Ji Lee, Su-Jung Kim, Young-Il Hahn, Hyo-Jin Yoon, Bitnara Han, Kyeojin Kim, Seungbeom Lee, Kwang Pyo Kim, Young Ger Suh, Hye-Kyung Na, Young-Joon Surh. 15-Keto prostaglandin E2 suppresses STAT3 signaling and inhibits breast cancer cell growth and progression.
Redox biology.
2019 05; 23(?):101175. doi:
10.1016/j.redox.2019.101175. [PMID: 31129031] - Robert J Evans, Katherine Pline, Catherine A Loynes, Sarah Needs, Maceler Aldrovandi, Jens Tiefenbach, Ewa Bielska, Rachel E Rubino, Christopher J Nicol, Robin C May, Henry M Krause, Valerie B O'Donnell, Stephen A Renshaw, Simon A Johnston. 15-keto-prostaglandin E2 activates host peroxisome proliferator-activated receptor gamma (PPAR-γ) to promote Cryptococcus neoformans growth during infection.
PLoS pathogens.
2019 03; 15(3):e1007597. doi:
10.1371/journal.ppat.1007597. [PMID: 30921435] - Julio Mesa, Cristina Alsina, Udo Oppermann, Xavier Parés, Jaume Farrés, Sergio Porté. Human prostaglandin reductase 1 (PGR1): Substrate specificity, inhibitor analysis and site-directed mutagenesis.
Chemico-biological interactions.
2015 Jun; 234(?):105-13. doi:
10.1016/j.cbi.2015.01.021. [PMID: 25619643] - Stacy Gelhaus Wendell, Franca Golin-Bisello, Sally Wenzel, Robert W Sobol, Fernando Holguin, Bruce A Freeman. 15-Hydroxyprostaglandin dehydrogenase generation of electrophilic lipid signaling mediators from hydroxy ω-3 fatty acids.
The Journal of biological chemistry.
2015 Feb; 290(9):5868-80. doi:
10.1074/jbc.m114.635151. [PMID: 25586183] - Yu-Hsiang Yu, Yi-Cheng Chang, Tseng-Hsiung Su, Jiun-Yi Nong, Chao-Chin Li, Lee-Ming Chuang. Prostaglandin reductase-3 negatively modulates adipogenesis through regulation of PPARγ activity.
Journal of lipid research.
2013 Sep; 54(9):2391-9. doi:
10.1194/jlr.m037556. [PMID: 23821743] - Dongdong Lu, Chang Han, Tong Wu. 15-hydroxyprostaglandin dehydrogenase-derived 15-keto-prostaglandin E2 inhibits cholangiocarcinoma cell growth through interaction with peroxisome proliferator-activated receptor-γ, SMAD2/3, and TAP63 proteins.
The Journal of biological chemistry.
2013 Jul; 288(27):19484-502. doi:
10.1074/jbc.m113.453886. [PMID: 23687300] - Katsuko Shiraya, Taku Hirata, Ryo Hatano, Shushi Nagamori, Pattama Wiriyasermkul, Promsuk Jutabha, Mitsunobu Matsubara, Shigeaki Muto, Hidekazu Tanaka, Shinji Asano, Naohiko Anzai, Hitoshi Endou, Akira Yamada, Hiroyuki Sakurai, Yoshikatsu Kanai. A novel transporter of SLC22 family specifically transports prostaglandins and co-localizes with 15-hydroxyprostaglandin dehydrogenase in renal proximal tubules.
The Journal of biological chemistry.
2010 Jul; 285(29):22141-51. doi:
10.1074/jbc.m109.084426. [PMID: 20448048] - Gregory S Harmon, Darren S Dumlao, Damian T Ng, Kim E Barrett, Edward A Dennis, Hui Dong, Christopher K Glass. Pharmacological correction of a defect in PPAR-gamma signaling ameliorates disease severity in Cftr-deficient mice.
Nature medicine.
2010 Mar; 16(3):313-8. doi:
10.1038/nm.2101. [PMID: 20154695] - Jinsheng Yang, Charles E Petersen, Chung-Eun Ha, Nadhipuram V Bhagavan. Structural insights into human serum albumin-mediated prostaglandin catalysis.
Protein science : a publication of the Protein Society.
2002 Mar; 11(3):538-45. doi:
10.1110/ps.28702. [PMID: 11847277] - S Sakuma, Y Fujimoto, Y Miyata, K Yamane, H Nishida, T Fujita. Inhibition of 15-hydroxy prostaglandin dehydrogenase activity in rabbit gastric antral mucosa by 13-hydroperoxyoctadecadienoic acid.
Prostaglandins, leukotrienes, and essential fatty acids.
1994 Dec; 51(6):425-30. doi:
10.1016/0952-3278(94)90060-4. [PMID: 7708809] - S Sakuma, Y Fujimoto, M Okumura, H Nishida, I Yamamoto, T Fujita. The effects of arachidonic acid and its CoA ester on the catabolism of prostaglandin E2 in rabbit kidney cortex.
Biochemistry international.
1992 Jul; 27(2):291-9. doi:
. [PMID: 1323964] - E D Watson, C R Stokes, F J Bourne. Effect of exogenous ovarian steroids on the uterine luminal prostaglandins in ovariectomised mares with experimental endometritis.
Research in veterinary science.
1988 May; 44(3):361-5. doi:
10.1016/s0034-5288(18)30872-5. [PMID: 3165540] - A R Morrison, J R Crowley. Identification of an unusual cyclooxygenase metabolite of arachidonic acid in rabbit renal medulla.
Archives of biochemistry and biophysics.
1984 Nov; 234(2):413-7. doi:
10.1016/0003-9861(84)90287-x. [PMID: 6437329] - D G Chang, H H Tai. Characterization of two enzyme proteins catalyzing NADP+/NADPH-dependent oxidoreduction of prostaglandins at C-9 and C-15 from swine kidney.
Archives of biochemistry and biophysics.
1982 Apr; 214(2):464-74. doi:
10.1016/0003-9861(82)90050-9. [PMID: 6807198]
