Aminopterin (BioDeep_00000405463)

Main id: BioDeep_00000018076

 


代谢物信息卡片


2-[[4-[(2,4-diaminopteridin-6-yl)methylamino]benzoyl]amino]pentanedioic acid

  化学式: C19H20N8O5 (440.1557)
中文名称: 4-氨基蝶呤 水合物
  谱图信息: 最多检出来源 () %

分子结构信息

SMILES: C1=CC(=CC=C1C(=O)NC(CCC(=O)O)C(=O)O)NCC2=CN=C3C(=N2)C(=NC(=N3)N)N
InChI: InChI=1S/C19H20N8O5/c20-15-14-16(27-19(21)26-15)23-8-11(24-14)7-22-10-3-1-9(2-4-10)17(30)25-12(18(31)32)5-6-13(28)29/h1-4,8,12,22H,5-7H2,(H,25,30)(H,28,29)(H,31,32)(H4,20,21,23,26,27)


描述信息

C274 - Antineoplastic Agent > C186664 - Cytotoxic Chemotherapeutic Agent > C272 - Antimetabolite
C471 - Enzyme Inhibitor > C2153 - Dihydrofolate Reductase Inhibitor
D004791 - Enzyme Inhibitors > D005493 - Folic Acid Antagonists

同义名列表

115 个代谢物同义名

Aminopterin; 2-[[4-[(2,4-diaminopteridin-6-yl)methylamino]benzoyl]amino]pentanedioic acid; 4-Aminopteroyl-L-glutamic acid; 4-Aminofolic acid; 4-amino-PGA; (2S)-2-[(4-{[(2,4-diaminopteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid; (2S)-2-[[[4-[(2,4-diamino-6-pteridinyl)methylamino]phenyl]-oxomethyl]amino]pentanedioic acid; (2S)-2-[[4-[(2,4-diaminopteridin-6-yl)methylamino]benzoyl]amino]pentanedioic acid; (2S)-2-[[4-[[(2,4-Diaminopteridin-6-yl)methyl]amino]benzoyl]amino]pentanedioic Acid (4-Aminofolic Acid, Aminopterin); (2S)-2-[[4-[[2,4-bis(azanyl)pteridin-6-yl]methylamino]phenyl]carbonylamino]pentanedioic acid; (4-(((2,4-diaminopteridin-6-yl)methyl)amino)benzoyl)-L-glutamic acid; (S)-2-(4-(((2,4-Diaminopteridin-6-yl)methyl)amino)benzamido)pentanedioic acid; (S)-2-(4-((2,4-diaminopteridin-6-yl)methylamino)benzamido)pentanedioic acid; 04J; 2-((4-(((2,4-diaminopteridin-6-yl)methyl)amino)phenyl)formamido)pentanedioic acid; 2-[(4-{[(2,4-diaminopteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid; 4-26-00-03831 (Beilstein Handbook Reference); 4-Amino pteroylglutamic acid; 4-Amino-4-deoxypteroylglutamate; 4-Amino-4-desoxy-pteroylglutaminsaeure; 4-Amino-PGA(O'Neil, M.J. (ed.). The Merck Index-An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 83); 4-Amino-PGA[O'Neil, M.J. (ed.). The Merck Index-An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 83]; 4-Aminofolate; 4-Aminofolic acid(O'Neil, M.J. (ed.). The Merck Index-An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 83); 4-Aminofolic acid[O'Neil, M.J. (ed.). The Merck Index-An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 83]; 4-Aminopteroic acid; 4-Aminopteroylglutamate; 4-Aminopteroylglutamic acid; 4-Aminopteroylglutamic acid(O'Neil, M.J. (ed.). The Merck Index-An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 83); 4-Aminopteroylglutamic acid[O'Neil, M.J. (ed.). The Merck Index-An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 83]; 4'-Amino-folsaeure; 4'-Desoxy-4'-aminofolsaeure; 4'Aminofolsaeure; 4'Desoxy4'aminofolsaeure; 4Amino pteroylglutamic acid; 4Amino4deoxypteroylglutamate; 4Amino4desoxypteroylglutaminsaeure; 4Aminofolic acid; 4AminoPGA; 4Aminopteroylglutamic acid; 4kn1; 54-62-6 (free acid); A-Ninopterin; AI3-26079; Aminopteridine; Aminopterin (Standard); AMINOPTERIN [HSDB]; AMINOPTERIN [MI]; AMINOPTERIN [WHO-DD]; Aminopterin dihydrate; Aminopterin hydrate; Aminopterin Sodium; Aminopterin, Disodium Salt; Aminopterin, Hybri-Max(TM), 50 x, gamma-irradiated, lyophilized powder, BioXtra, suitable for hybridoma; Aminopterin, powder; Aminopterin, powder, BioReagent, suitable for cell culture; Aminopterine; Aminopterinum; Aminopteroylglutamic acid; Aminotrexate; APGA; CAS-54-62-6; Disodium Salt Aminopterin; Folic acid, 4-amino-; Folic acid, 4amino; Glutamic acid, N-(p-(((2,4-diamino-6-pteridinyl)methyl)amino)benzoyl)-, L-; Glutamic acid, N-[p-[[(2,4-diamino-6-pteridinyl)methyl]amino]benzoyl]-, L-; Glutamic acid, N(p(((2,4diamino6pteridinyl)methyl)amino)benzoyl), L; JYB41CTM2Q; Kyselina 4-aminolistova; Kyselina 4-Aminolistova (Czech); Kyselina 4-aminolistova [Czech]; Kyselina 4-aminopteroylglutamova; Kyselina 4-Aminopteroylglutamova (Czech); Kyselina 4-aminopteroylglutamova [Czech]; Kyselina 4aminolistova; Kyselina 4aminopteroylglutamova; Kyselina N-(p-((2,4-diamino-6-pteridinyl)methyl)benzoyl)-L(+)-glutamova; Kyselina N-(p-((2,4-diamino-6-pteridinyl)methyl)benzoyl)-L(+)-glutamova [Czech]; Kyselina N-(p-((2,4-diamino-6-pteridinylmethyl)amino)benzoyl)-L(+)-glutamova; Kyselina N-(p-((2,4-diamino-6-pteridinylmethyl)amino)benzoyl)-L(+)-glutamova [Czech]; KYSELINA N-(p-((2,4-DIAMINO-6-PTERIDINYLMETHYL)BENZOYL)-L(+)-GLUTAMOVA; KYSELINA N-(p-((2,4-DIAMINO-6-PTERIDINYLMETHYL)BENZOYL)-L(+)-GLUTAMOVA (Czech); Kyselina N(p((2,4diamino6pteridinyl)methyl)benzoyl)L(+)glutamova; Kyselina N(p((2,4diamino6pteridinylmethyl)amino)benzoyl)L(+)glutamova; L-Glutamic acid, N-(4-(((2,4-diamino-6-pteridinyl)methyl)amino)benzoyl)-; L-GLUTAMIC ACID, N-(4-((DIAMINO-6-PTERIDINYL)METHYL) AMINO)BENZOYL)-; L-GLUTAMIC ACID, N-[4-[(DIAMINO-6-PTERIDINYL)METHYL] AMINO]BENZOYL]-; L-Glutamic acid, N-[4-[[(2,4-diamino-6-pteridinyl)methyl]amino]benzoyl]-; L-N-(p-(((2,4-Diamino-6-pteridinyl)methyl)amino)benzoyl)-Glutamic acid; L-N-[p-[[(2,4-diamino-6-pteridinyl)methyl]amino]benzoyl]-Glutamic acid; LGlutamic acid, N(4(((2,4diamino6pteridinyl)methyl)amino)benzoyl); METHOTREXATE IMPURITY B (EP IMPURITY); METHOTREXATE IMPURITY B [EP IMPURITY]; METHOTREXATE RC B ( AMINOPTERIN); Minopterin; N-(1-((2,4-Diamino-6-pteridinylmethyl)amino)benzoyl)glutaminsaeure; N-(4-(((2,4-Diamino-6-pteridinyl)methyl)amino)benzoyl)-L-glutamic acid; N-(4-(((2,4-Diamino-6-pteridyl)-methyl)amino)benzoyl)-L-glutamic acid; N-(4-(((2,4-diaminopteridin-6-yl)methyl)amino)benzoyl)-L-glutamic acid; N-(4-((2,4-DIAMINO-6-PTERIDINYL)METHYL)AMINO)BENZOYL)-L-GLUTAMIC ACID; N-(4-{[(2,4-diaminopteridin-6-yl)methyl]amino}benzoyl)-L-glutamic acid; N-(P-(((2,4-DIAMINO-6-PTERIDINYL)METHYL)AMINO)BENZOYL)GLUTAMIC ACID; N-[4-[[(2,4-Diamino-6-pteridinyl)methyl]amino]benzoyl]-L-glutamic acid; N-[4-[[(2,4-Diamino-6-pteridinyl)methyl]amino]benzoyl]-L-glutamic acid;4-Aminofolic acid, 4-aminopteroyl-L-glutamic acid, 4-amino-PG A;NSC 739; N(1((2,4Diamino6pteridinylmethyl)amino)benzoyl)glutaminsaeure; N(4(((2,4Diamino6pteridinyl)methyl)amino)benzoyl)Lglutamic acid; N(4(((2,4Diamino6pteridyl)methyl)amino)benzoyl)Lglutamic acid; Pteramina; Pteramina (Czech); Pteramina [Czech]; Sodium, Aminopterin; Tox21_110069; Tox21_300627; UNII-JYB41CTM2Q



数据库引用编号

12 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome()

BioCyc()

PlantCyc()

代谢反应

个相关的代谢反应过程信息。

Reactome()

BioCyc()

WikiPathways()

Plant Reactome()

INOH()

PlantCyc()

COVID-19 Disease Map()

PathBank()

PharmGKB()

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


文献列表

  • Gabriela E Garcia, Yingjuan J Lu, Luan D Truong, Carlos A Roncal-Jiménez, Makoto Miyazaki, Shinobu Miyazaki-Anzai, Gabriel Cara-Fuentes, Ana Andres-Hernando, Miguel Lanaspa, Richard J Johnson, Christopher P Leamon. A Novel Treatment for Glomerular Disease: Targeting the Activated Macrophage Folate Receptor with a Trojan Horse Therapy in Rats. Cells. 2021 08; 10(8):. doi: 10.3390/cells10082113. [PMID: 34440885]
  • Haiping Zhang, Yang Yang, Junxin Li, Min Wang, Konda Mani Saravanan, Jinli Wei, Justin Tze-Yang Ng, Md Tofazzal Hossain, Maoxuan Liu, Huiling Zhang, Xiaohu Ren, Yi Pan, Yin Peng, Yi Shi, Xiaochun Wan, Yingxia Liu, Yanjie Wei. A novel virtual screening procedure identifies Pralatrexate as inhibitor of SARS-CoV-2 RdRp and it reduces viral replication in vitro. PLoS computational biology. 2020 12; 16(12):e1008489. doi: 10.1371/journal.pcbi.1008489. [PMID: 33382685]
  • Viola Previtali, Katarina Petrovic, Jorge Peiró Cadahía, Nikolaj Sten Troelsen, Mads H Clausen. Auxiliary in vitro and in vivo biological evaluation of hydrogen peroxide sensitive prodrugs of methotrexate and aminopterin for the treatment of rheumatoid arthritis. Bioorganic & medicinal chemistry. 2020 01; 28(2):115247. doi: 10.1016/j.bmc.2019.115247. [PMID: 31843461]
  • Kevin R Kelly, Nashat Gabrail, Steven Weitman, John Sarantopoulos, Anthony J Olszanski, William Edenfield, Jurgen Venitz, Guru Reddy, Allen Yang, Steven J Hasal, A Craig Lockhart. Phase 1 study evaluating the safety and pharmacokinetics of pralatrexate in relapsed/refractory advanced solid tumors and lymphoma patients with mild, moderate, and severe renal impairment. Cancer chemotherapy and pharmacology. 2016 Nov; 78(5):929-939. doi: 10.1007/s00280-016-3142-3. [PMID: 27638045]
  • Jordan P McPherson, Alaina Vrontikis, Courtney Sedillo, Ahmad S Halwani, Jeffrey A Gilreath. Pralatrexate Monitoring Using a Commercially Available Methotrexate Assay to Avoid Potential Drug Interactions. Pharmacotherapy. 2016 Feb; 36(2):e8-e11. doi: 10.1002/phar.1699. [PMID: 26809959]
  • Alan Menter, Breck Thrash, Christina Cherian, Larry H Matherly, Lei Wang, Aleem Gangjee, Joel R Morgan, Dean Y Maeda, Aaron D Schuler, Stuart J Kahn, John A Zebala. Intestinal transport of aminopterin enantiomers in dogs and humans with psoriasis is stereoselective: evidence for a mechanism involving the proton-coupled folate transporter. The Journal of pharmacology and experimental therapeutics. 2012 Sep; 342(3):696-708. doi: 10.1124/jpet.112.195479. [PMID: 22653877]
  • Li-Te Chin, Pei-Ru Huang, Kuang-Yu Hu, Nai-Kuei Huang, Cheng-Di Chiu, Ai-Ling Hour, Hao-Ai Shui, Chi-Hong Chu, Han-Min Chen. A proteomics-based translational approach reveals an antifolate resistance inherent in human plasma derived from blood donation. Journal of proteome research. 2010 Jun; 9(6):3091-102. doi: 10.1021/pr100005u. [PMID: 20707402]
  • Robin E Norris, Peter C Adamson. Clinical potency of methotrexate, aminopterin, talotrexin and pemetrexed in childhood leukemias. Cancer chemotherapy and pharmacology. 2010 May; 65(6):1125-30. doi: 10.1007/s00280-009-1120-8. [PMID: 19784838]
  • N Sobreira, M Cernach, D Batista, D Brunoni, A Perez. Pseudoaminopterin syndrome: clinical report with new characteristics. American journal of medical genetics. Part A. 2009 Dec; 149A(12):2843-8. doi: 10.1002/ajmg.a.33125. [PMID: 19938091]
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  • Tim Mant, Stipo Jurcevic, Cameron Szakacs, Luthando Adams, John Boland, Lawrence Arthur Hewitt. Two single-center, double-blind, randomized, placebo-controlled, phase I studies to investigate the tolerability and pharmacokinetics of CH-1504, an antifolate, in healthy male subjects. Clinical therapeutics. 2008 Jan; 30(1):131-42. doi: 10.1016/j.clinthera.2008.01.017. [PMID: 18343249]
  • Daniel Wolff, Eva Frei, Nicole Hofmeister, Beate Steiner, Hans-Dieter Kleine, Christian Junghanss, Kathrin Sievert, Harald Terpe, Hans-Hermann Schrenk, Mathias Freund, Gernot Hartung. Methotrexate-albumin and aminopterin-albumin effectively prevent experimental acute graft-versus-host disease. Transplantation. 2006 Aug; 82(4):527-33. doi: 10.1097/01.tp.0000229451.40286.64. [PMID: 16926597]
  • Matthew G Fury, Lee M Krug, Christopher G Azzoli, Sunil Sharma, Nancy Kemeny, Nian Wu, Mark G Kris, Naiyer A Rizvi. A phase I clinical pharmacologic study of pralatrexate in combination with probenecid in adults with advanced solid tumors. Cancer chemotherapy and pharmacology. 2006 May; 57(5):671-7. doi: 10.1007/s00280-005-0080-x. [PMID: 16136310]
  • Sebastian M J Klaus, Edmund R S Kunji, Gale G Bozzo, Alexandre Noiriel, Rocío Díaz de la Garza, Gilles J C Basset, Stéphane Ravanel, Fabrice Rébeillé, Jesse F Gregory, Andrew D Hanson. Higher plant plastids and cyanobacteria have folate carriers related to those of trypanosomatids. The Journal of biological chemistry. 2005 Nov; 280(46):38457-63. doi: 10.1074/jbc.m507432200. [PMID: 16162503]
  • Lee M Krug, Christopher G Azzoli, Mark G Kris, Vincent A Miller, Nushmia Z Khokhar, William Tong, Michelle S Ginsberg, Ennapadam Venkatraman, Leslie Tyson, Barbara Pizzo, Valerie Baez, Kenneth K Ng, F M Sirotnak. 10-propargyl-10-deazaaminopterin: an antifolate with activity in patients with previously treated non-small cell lung cancer. Clinical cancer research : an official journal of the American Association for Cancer Research. 2003 Jun; 9(6):2072-8. doi: NULL. [PMID: 12796370]
  • Hieronim Jakubowski, Andrzej Guranowski. Metabolism of homocysteine-thiolactone in plants. The Journal of biological chemistry. 2003 Feb; 278(9):6765-70. doi: 10.1074/jbc.m211819200. [PMID: 12496251]
  • N Eschen, U Bauder-Wüst, E Frei, H H Schrenk, H Sinn, P Kremer, I Kiprianova, G Hartung. Aminopterin-human serum albumin conjugate (AP-HSA): uptake and cytotoxic effects in tumor cell lines. International journal of clinical pharmacology and therapeutics. 2002 Dec; 40(12):564-6. doi: 10.5414/cpp40564. [PMID: 12503815]
  • Paul Kremer, Gernot Hartung, Ulrike Bauder-Wüst, Hans-Hermann Schrenk, Andreas Wunder, Stefan Heckl, Uwe Zillmann, Hannsjörg Sinn. Efficacy and tolerability of an aminopterin-albumin conjugate in tumor-bearing rats. Anti-cancer drugs. 2002 Jul; 13(6):615-23. doi: 10.1097/00001813-200207000-00008. [PMID: 12172507]
  • John L Andreassi, Richard G Moran. Mouse folylpoly-gamma-glutamate synthetase isoforms respond differently to feedback inhibition by folylpolyglutamate cofactors. Biochemistry. 2002 Jan; 41(1):226-35. doi: 10.1021/bi015644d. [PMID: 11772020]
  • F M Sirotnak, H G Wendel, W G Bornmann, W P Tong, V A Miller, H I Scher, M G Kris. Co-administration of probenecid, an inhibitor of a cMOAT/MRP-like plasma membrane ATPase, greatly enhanced the efficacy of a new 10-deazaaminopterin against human solid tumors in vivo. Clinical cancer research : an official journal of the American Association for Cancer Research. 2000 Sep; 6(9):3705-12. doi: . [PMID: 10999764]
  • A Takeuchi, S Masuda, H Saito, Y Hashimoto, K Inui. Trans-stimulation effects of folic acid derivatives on methotrexate transport by rat renal organic anion transporter, OAT-K1. The Journal of pharmacology and experimental therapeutics. 2000 Jun; 293(3):1034-9. doi: NULL. [PMID: 10869408]
  • P J Hynds, D Robinson, C Robinson. The sec-independent twin-arginine translocation system can transport both tightly folded and malfolded proteins across the thylakoid membrane. The Journal of biological chemistry. 1998 Dec; 273(52):34868-74. doi: 10.1074/jbc.273.52.34868. [PMID: 9857014]
  • K Roy, B Tolner, J H Chiao, F M Sirotnak. A single amino acid difference within the folate transporter encoded by the murine RFC-1 gene selectively alters its interaction with folate analogues. Implications for intrinsic antifolate resistance and directional orientation of the transporter within the plasma membrane of tumor cells. The Journal of biological chemistry. 1998 Jan; 273(5):2526-31. doi: 10.1074/jbc.273.5.2526. [PMID: 9446553]
  • V Prabhu, K B Chatson, H Lui, G D Abrams, J King. Effects of sulfanilamide and methotrexate on 13C fluxes through the glycine decarboxylase/serine hydroxymethyltransferase enzyme system in arabidopsis. Plant physiology. 1998 Jan; 116(1):137-44. doi: 10.1104/pp.116.1.137. [PMID: 9449840]
  • M J Edelman, D R Gandara, E A Perez, D Lau, I Lauder, C Turrell, M Uhrich, F Meyers. Phase I trial of edatrexate plus carboplatin in advanced solid tumors: amelioration of dose-limiting mucositis by ice chip cryotherapy. Investigational new drugs. 1998; 16(1):69-75. doi: 10.1023/a:1006026928733. [PMID: 9740546]
  • C H Takimoto. Antifolates in clinical development. Seminars in oncology. 1997 Oct; 24(5 Suppl 18):S18-40. doi: ". [PMID: 9420020]
  • H Su, T L Chen, F H Hausheer, E K Rowinsky. Novel high-performance liquid chromatographic assay using fluorescence detection for the quantitation of plasma gamma-methylene-10-deazaaminopterin and its major metabolite, 7-hydroxy-gamma-methylene-10-deazaaminopterin, in patients with solid cancers in a phase I trial. Journal of chromatography. B, Biomedical sciences and applications. 1997 Aug; 695(2):401-8. doi: 10.1016/s0378-4347(97)00205-3. [PMID: 9300877]
  • R Dreicer, K J Propert, T Kuzel, J M Kirkwood, P J O'Dwyer, P J Loehrer. A phase II trial of edatrexate in patients with advanced renal cell carcinoma. An Eastern Cooperative Oncology Group study. American journal of clinical oncology. 1997 Jun; 20(3):251-3. doi: 10.1097/00000421-199706000-00008. [PMID: 9167747]
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