Prostaglandin F2alpha (BioDeep_00000002977)

 

Secondary id: BioDeep_00000014601, BioDeep_00000629488, BioDeep_00001867856

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite BioNovoGene_Lab2019


代谢物信息卡片


(5E)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]hept-5-enoic acid

化学式: C20H34O5 (354.2406)
中文名称: 前列腺素 F2a, 地诺前列素
谱图信息: 最多检出来源 Homo sapiens(feces) 30.86%

Reviewed

Last reviewed on 2024-09-13.

Cite this Page

Prostaglandin F2alpha. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/prostaglandin_f2alpha (retrieved 2024-12-22) (BioDeep RN: BioDeep_00000002977). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: CCCCCC(C=CC1C(CC(C1CC=CCCCC(=O)O)O)O)O
InChI: InChI=1S/C20H34O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,15-19,21-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4+,13-12+/t15-,16+,17+,18-,19+/m0/s1

描述信息

Prostaglandin F2a (PGF2) is one of the earliest discovered and most common prostaglandins. It is actively biosynthesized in various organs of mammals and exhibits a variety of biological activities, including contraction of pulmonary arteries. It is used in medicine to induce labor and as an abortifacient. PGF2a binds to the Prostaglandin F2 receptor (PTGFR) which is a member of the G-protein coupled receptor family. PGF2-alpha mediates luteolysis. Luteolysis is the structural and functional degradation of the corpus luteum (CL) that occurs at the end of the luteal phase of both the estrous and menstrual cycles in the absence of pregnancy. PGF2 may also be involved in modulating intraocular pressure and smooth muscle contraction in the uterus and gastrointestinal tract sphincters. PGF2 is mainly synthesized directly from PGH2 by PGH2 9,11-endoperoxide reductase. A small amount of PGF2 is also produced from PGE2 by PGE2 9-ketoreductase. A PGF2 epimer has been reported to exhibit various biological activities, and its levels are increased in bronchoalveolar lavage fluid, plasma, and urine in patients with mastocytosis and bronchial asthma. PGF2 is synthesized from PGD2 by PGD2 11-ketoreductase. (PMID: 16475787). Prostaglandins 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.
Prostaglandin F2a (PGF2) is one of the earliest discovered and most common prostaglandins. It is actively biosynthesized in various organs of mammals and exhibits a variety of biological activities, including contraction of pulmonary arteries. It is used in medicine to induce labor and as an abortifacient. PGF2a binds to the Prostaglandin F2 receptor (PTGFR) which is a member of the G-protein coupled receptor family. PGF2-alpha mediates luteolysis. Luteolysis is the structural and functional degradation of the corpus luteum (CL) that occurs at the end of the luteal phase of both the estrous and menstrual cycles in the absence of pregnancy. PGF2 may also be involved in modulating intraocular pressure and smooth muscle contraction in the uterus and gastrointestinal tract sphincters. PGF2 is mainly synthesized directly from PGH2 by PGH2 9,11-endoperoxide reductase. A small amount of PGF2 is also produced from PGE2 by PGE2 9-ketoreductase. A PGF2 epimer has been reported to exhibit various biological activities, and its levels are increased in bronchoalveolar lavage fluid, plasma, and urine in patients with mastocytosis and bronchial asthma. PGF2 is synthesized from PGD2 by PGD2 11-ketoreductase. (PMID: 16475787)
G - Genito urinary system and sex hormones > G02 - Other gynecologicals > G02A - Uterotonics > G02AD - Prostaglandins
Chemical was purchased from CAY16010 (Lot 171332-126); Diagnostic ions: 353.2, 309.2, 281.1, 253.0, 193.1
D012102 - Reproductive Control Agents > D000019 - Abortifacient Agents
D012102 - Reproductive Control Agents > D010120 - Oxytocics
C78568 - Prostaglandin Analogue
KEIO_ID P066
Dinoprost (Prostaglandin F2α) is an orally active, potent prostaglandin F (PGF) receptor (FP receptor) agonist. Dinoprost is a luteolytic hormone produced locally in the endometrial luminal epithelium and corpus luteum (CL). Dinoprost plays a key role in the onset and progression of labour[1][2].

同义名列表

60 个代谢物同义名

(5E)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]hept-5-enoic acid; (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]cyclopentyl]hept-5-enoic acid; (5Z,13E)-(15S)-9-alpha,11-alpha,15-Trihydroxyprosta-5,13-dienoic acid; 7-[3,5-Dihydroxy-2-(3-hydroxy-1-octenyl)cyclopentyl]-5-heptenoic acid; 9,11,15-Trihydroxy-(5Z,9a,11a,13E,15S)-prosta-5,13-dien-1-Oic acid; (5Z,9a,11a,13E,15S)-9,11,15-Trihydroxy-prosta-5,13-dien-1-Oic acid; (5Z,9alpha,11alpha,13E,15S)-9,11,15-Trihydroxyprosta-5,13-dienoate; (5Z,13E)-(15S)-9-alpha,11-alpha,15-Trihydroxyprosta-5,13-dienoate; 7-[3,5-Dihydroxy-2-(3-hydroxy-1-octenyl)cyclopentyl]-5-heptenoate; (5Z,13E)-(15S)-9alpha,11alpha,15-Trihydroxyprosta-5,13-dienoate; 9,11,15-Trihydroxy-(5Z,9a,11a,13E,15S)-prosta-5,13-dien-1-Oate; (5Z,9a,11a,13E,15S)-9,11,15-Trihydroxy-prosta-5,13-dien-1-Oate; (9alpha,11alpha,15)-Trihydroxyprosta-(5Z,13E)-dien-1-Oic acid; (5Z,13E,15S)-9a,11a,15-Trihydroxyprosta-5,13-dien-1-Oic acid; 9a,11a,15(S)-Trihydroxy-5-cis-13-trans-prostadienoic acid; (9alpha,11alpha,15)-Trihydroxyprosta-(5Z,13E)-dien-1-Oate; (5Z,13E,15S)-9a,11a,15-Trihydroxyprosta-5,13-dien-1-Oate; 9a,11a,15(S)-Trihydroxy-5-cis-13-trans-prostadienoate; 9,11,15-Trihydroxyprosta-5Z,13E-dien-1-Oic acid; 9,11,15-Trihydroxyprosta-5Z,13E-dien-1-Oate; Prostaglandin F2a;PGF2alpha; L-Prostaglandin F2-alpha; F2 alpha, Prostaglandin; Prostaglandin F2 alpha; F2alpha, Prostaglandin; (+)-Prostaglandin F2a; Prostaglandin F2alpha; 9alpha,11beta PGF2; 9alpha,11beta-PGF2; Prostin F 2 alpha; Prostaglandin F2a; Prostaglandin F2; F2a Isoprostane; 5-trans-PGF2α; L-PGF2-alpha; 9a,11a-PGF2a; Prostarmon F; tromethamine; 9a,11a-PGF2; Enzaprost F; alpha, PGF2; Amoglandin; PGF2 alpha; PGF2α Prostamate; Protamodin; Dinifertin; Glandin N; Enzaprost; PGF2alpha; Panacelan; Dinoprost; Estrofan; Cyclosin; U 14583; PGF2a; PGF2; Prostaglandin F2α; PGF2α; Prostaglandin F2alpha



数据库引用编号

40 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(10)

BioCyc(0)

PlantCyc(0)

代谢反应

175 个相关的代谢反应过程信息。

Reactome(169)

BioCyc(0)

WikiPathways(5)

Plant Reactome(0)

INOH(1)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

5 个相关的物种来源信息

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。

亚细胞结构定位 关联基因列表
Cytoplasm 8 AKT1, ALB, EDN1, MYLK, PLA2G12A, POMC, PTGS1, VEGFA
Peripheral membrane protein 1 PTGS1
Endoplasmic reticulum membrane 4 CYP19A1, PTGDS, PTGES, PTGS1
Nucleus 3 AKT1, ALB, VEGFA
cytosol 4 AKT1, ALB, IL1B, MYLK
centrosome 1 ALB
nucleoplasm 1 AKT1
Cell membrane 4 AKT1, PTGER1, PTGER4, TNF
Cleavage furrow 1 MYLK
lamellipodium 2 AKT1, MYLK
Multi-pass membrane protein 4 CYP19A1, PTGER1, PTGER4, PTGES
Synapse 1 MYLK
cell cortex 1 AKT1
cell surface 3 PLA2G1B, TNF, VEGFA
glutamatergic synapse 1 AKT1
Golgi apparatus 4 ALB, PTGDS, PTGS1, VEGFA
Golgi membrane 1 INS
neuronal cell body 1 TNF
postsynapse 1 AKT1
Cytoplasm, cytosol 1 IL1B
Lysosome 1 IL1B
plasma membrane 6 AKT1, IFNLR1, MYLK, PTGER1, PTGER4, TNF
Membrane 6 AKT1, CYP19A1, IFNLR1, PTGER4, PTGES, VEGFA
extracellular exosome 3 ALB, PTGDS, PTGS1
endoplasmic reticulum 3 ALB, CYP19A1, VEGFA
extracellular space 11 ALB, CRP, CXCL8, EDN1, IL1B, INS, PLA2G1B, POMC, PTGDS, TNF, VEGFA
perinuclear region of cytoplasm 2 PTGDS, PTGES
adherens junction 1 VEGFA
protein-containing complex 2 AKT1, ALB
intracellular membrane-bounded organelle 1 PTGS1
Microsome membrane 2 CYP19A1, PTGS1
Single-pass type I membrane protein 1 IFNLR1
Secreted 11 ALB, CRP, CXCL8, EDN1, IL1B, INS, PLA2G12A, PLA2G1B, POMC, PTGDS, VEGFA
extracellular region 12 ALB, CRP, CXCL8, EDN1, IL1B, INS, PLA2G12A, PLA2G1B, POMC, PTGDS, TNF, VEGFA
basal part of cell 1 EDN1
anchoring junction 1 ALB
photoreceptor outer segment 1 PTGS1
Nucleus membrane 1 PTGDS
nuclear membrane 1 PTGDS
external side of plasma membrane 1 TNF
Secreted, extracellular space, extracellular matrix 1 VEGFA
actin cytoskeleton 1 MYLK
microtubule cytoskeleton 1 AKT1
cell-cell junction 1 AKT1
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
vesicle 1 AKT1
Cell projection, lamellipodium 1 MYLK
Cytoplasm, perinuclear region 2 PTGDS, PTGES
Membrane raft 1 TNF
spindle 1 AKT1
extracellular matrix 1 VEGFA
Mitochondrion intermembrane space 1 AKT1
mitochondrial intermembrane space 1 AKT1
secretory granule 3 IL1B, POMC, VEGFA
neuron projection 1 PTGS1
ciliary basal body 2 AKT1, ALB
phagocytic cup 1 TNF
centriole 1 ALB
spindle pole 1 ALB
blood microparticle 1 ALB
Endomembrane system 1 PTGS1
endosome lumen 1 INS
stress fiber 1 MYLK
secretory granule lumen 2 INS, POMC
Golgi lumen 1 INS
endoplasmic reticulum lumen 2 ALB, INS
platelet alpha granule lumen 2 ALB, VEGFA
transport vesicle 2 EDN1, INS
Secreted, extracellular exosome 1 IL1B
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
nuclear envelope lumen 1 PTGES
Cytoplasm, cytoskeleton, stress fiber 1 MYLK
Rough endoplasmic reticulum 1 PTGDS
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
rough endoplasmic reticulum lumen 1 EDN1
Weibel-Palade body 1 EDN1
[N-VEGF]: Cytoplasm 1 VEGFA
[VEGFA]: Secreted 1 VEGFA
[Isoform L-VEGF189]: Endoplasmic reticulum 1 VEGFA
[Isoform VEGF121]: Secreted 1 VEGFA
[Isoform VEGF165]: Secreted 1 VEGFA
VEGF-A complex 1 VEGFA
ciliary transition fiber 1 ALB
interleukin-28 receptor complex 1 IFNLR1
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Yazhen Xie, Haifeng Xu, Zhijuan Gu. Ge-gen decoction alleviates primary dysmenorrhoea symptoms in a rat model. Journal of obstetrics and gynaecology : the journal of the Institute of Obstetrics and Gynaecology. 2024 Dec; 44(1):2337691. doi: 10.1080/01443615.2024.2337691. [PMID: 38594870]
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  • Liu-Jun Wu, Yan Chen, Zi-Wei Lin, Chen Sun, Liang Xiong, Xiao-Fang Xie, Cheng Peng. [Therapeutic effect of Leonuri Herba aqueous decoction on primary dysmenorrhea in rats and its metabolomic analysis]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2023 Nov; 48(22):6093-6106. doi: 10.19540/j.cnki.cjcmm.20230803.401. [PMID: 38114217]
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  • Michele R Plewes, Emilia Przygrodzka, Corrine F Monaco, Alexandria P Snider, Jessica A Keane, Patrick D Burns, Jennifer R Wood, Andrea S Cupp, John S Davis. Prostaglandin F2α regulates mitochondrial dynamics and mitophagy in the bovine corpus luteum. Life science alliance. 2023 07; 6(7):. doi: 10.26508/lsa.202301968. [PMID: 37188480]
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  • Xing Wang, Bin Wang, Man Cheng, Linling Yu, Wei Liu, Xiuquan Nie, Mengyi Wang, Min Zhou, Weihong Chen. Lipid peroxidation mediates the association between iron overload and liver injury: cross-sectional and longitudinal analyses in general Chinese urban adults. Environmental science and pollution research international. 2023 Apr; ?(?):. doi: 10.1007/s11356-023-26702-1. [PMID: 37022540]
  • Burcu Azak Pazarlar, Cansu Bilister Egilmez, Mumin Alper Erdogan, Oytun Erbas. Immunosuppressant Tacrolimus Treatment Delays Acute Seizure Occurrence, Reduces Elevated Oxidative Stress, and Reverses PGF2α Burst in the Brain of PTZ-Treated Rats. Neurochemical research. 2023 Feb; ?(?):. doi: 10.1007/s11064-023-03885-0. [PMID: 36780043]
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  • Kuo-Shyang Jeng, Po-Yu Cheng, Yueh-Hsien Lin, Po-Chun Liu, Ping-Hui Tseng, Yu-Chao Wang, Chiung-Fang Chang, Chuen-Miin Leu. Aldo-keto reductase family member C3 (AKR1C3) promotes hepatocellular carcinoma cell growth by producing prostaglandin F2α. Oncology research. 2023; 32(1):163-174. doi: 10.32604/or.2023.030975. [PMID: 38188684]
  • Monika Jamioł, Magdalena Sozoniuk, Jacek Wawrzykowski, Marta Kankofer. Effect of Sex Steroids and PGF2α on the Expression of Their Receptors and Decorin in Bovine Caruncular Epithelial Cells in Early-Mid Pregnancy. Molecules (Basel, Switzerland). 2022 Nov; 27(21):. doi: 10.3390/molecules27217420. [PMID: 36364246]
  • Ana Maria Murta Santi, Juliana Martins Ribeiro, João Luís Reis-Cunha, Gabriela de Assis Burle-Caldas, Isabella Fernandes Martins Santos, Paula Alves Silva, Daniela de Melo Resende, Daniella Castanheira Bartholomeu, Santuza Maria Ribeiro Teixeira, Silvane Maria Fonseca Murta. Disruption of multiple copies of the Prostaglandin F2alpha synthase gene affects oxidative stress response and infectivity in Trypanosoma cruzi. PLoS neglected tropical diseases. 2022 10; 16(10):e0010845. doi: 10.1371/journal.pntd.0010845. [PMID: 36260546]
  • Lin Ma, Dongxiao Sun, Guangli Xiu, Philip Lazarus, Anil Vachani, Trevor M Penning, Alexander S Whitehead, Joshua E Muscat. Quantification of Plasma 8-Isoprostane by High-Performance Liquid Chromatography with Tandem Mass Spectrometry in a Case-Control Study of Lung Cancer. International journal of environmental research and public health. 2022 09; 19(19):. doi: 10.3390/ijerph191912488. [PMID: 36231826]
  • Yong-Moon Mark Park, Jenna Lilyquist, Thomas J Van't Erve, Katie M O'Brien, Hazel B Nichols, Ginger L Milne, Clarice R Weinberg, Dale P Sandler. Association of dietary and plasma carotenoids with urinary F2-isoprostanes. European journal of nutrition. 2022 Aug; 61(5):2711-2723. doi: 10.1007/s00394-022-02837-8. [PMID: 35253072]
  • Juan Carlos Tschopp, Alejandro J Macagno, Reuben J Mapletoft, Alejo Menchaca, Gabriel A Bó. Effect of the addition of GnRH and a second prostaglandin F2α treatment on pregnancy per artificial insemination in lactating dairy cows submitted to an estradiol/progesterone-based timed-AI protocol. Theriogenology. 2022 Aug; 188(?):63-70. doi: 10.1016/j.theriogenology.2022.05.019. [PMID: 35667231]
  • Abolfazl Hajibemani, Hossein Sheikhalislami, Mohammad Javad Behzadi Shahrbabak, Razi Jafari Jozani, Mohammad Mehdi Ommati. Effect of PGF2α and GnRH administration on reproductive performance in Ghezel ewes. Prostaglandins & other lipid mediators. 2022 08; 161(?):106640. doi: 10.1016/j.prostaglandins.2022.106640. [PMID: 35605836]
  • Ying Sun, Yan Yan, Xuejun Kang. Packed-Fiber Solid Phase-Extraction Coupled with HPLC-MS/MS for Rapid Determination of Lipid Oxidative Damage Biomarker 8-Iso-Prostaglandin F2α in Urine. Molecules (Basel, Switzerland). 2022 Jul; 27(14):. doi: 10.3390/molecules27144417. [PMID: 35889290]
  • Vanessa Peixoto de Souza, Jared Jensen, William Whitler, Charles T Estill, Cecily V Bishop. Increasing vitamin D levels to improve fertilization rates in cattle. Journal of animal science. 2022 Jul; 100(7):. doi: 10.1093/jas/skac168. [PMID: 35772760]
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  • Fernando Sánchez-Dávila, Víctor Adrián Hernández-Melo, Rogelio Alejandro Ledezma-Torres, Hugo Bernal-Barragán, Carlos Luna-Palomera, Rodolfo Ungerfeld. Cloprostenol enhances sexual behaviour and semen quality in growing lambs more effectively than Dinoprost. Reproduction in domestic animals = Zuchthygiene. 2022 Jun; 57(6):611-615. doi: 10.1111/rda.14101. [PMID: 35188980]
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  • A M Hubner, I F Canisso, P M Peixoto, A J Conley, F S Lima. Effect of gonadotropin-releasing hormone administered at the time of artificial insemination for cows detected in estrus by conventional estrus detection or an automated activity-monitoring system. Journal of dairy science. 2022 Jan; 105(1):831-841. doi: 10.3168/jds.2021-21011. [PMID: 34756436]
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