(6R)-Folinic acid (BioDeep_00000000726)
Main id: BioDeep_00000017460
human metabolite PANOMIX_OTCML-2023 blood metabolite
代谢物信息卡片
化学式: C20H23N7O7 (473.1659)
中文名称: 亚叶酸
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: C1C(N(C2=C(N1)N=C(NC2=O)N)C=O)CNC3=CC=C(C=C3)C(=O)NC(CCC(=O)O)C(=O)O
InChI: InChI=1S/C20H23N7O7/c21-20-25-16-15(18(32)26-20)27(9-28)12(8-23-16)7-22-11-3-1-10(2-4-11)17(31)24-13(19(33)34)5-6-14(29)30/h1-4,9,12-13,22H,5-8H2,(H,24,31)(H,29,30)(H,33,34)(H4,21,23,25,26,32)
描述信息
The active metabolite of folic acid. Leucovorin is used principally as its calcium salt as an antidote to folic acid antagonists which block the conversion of folic acid to folinic acid. [HMDB]
D020011 - Protective Agents > D000931 - Antidotes
C2140 - Adjuvant > C2078 - Folic Acid Derivative
Folinic acid (Leucovorin) is a biological folic acid and is generally administered along with Methotrexate (MTX) (HY-14519) as a rescue agent to decrease MTX-induced toxicity[1].
Folinic acid (Leucovorin) is a biological folic acid and is generally administered along with Methotrexate (MTX) (HY-14519) as a rescue agent to decrease MTX-induced toxicity[1].
同义名列表
53 个代谢物同义名
2-[(4-{[(2-amino-5-formyl-4-oxo-3,4,5,6,7,8-hexahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid; 2-[(4-{[(2-amino-5-formyl-4-oxo-3,6,7,8-tetrahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid; 2-[[4-[(2-amino-5-formyl-4-oxo-1,6,7,8-tetrahydropteridin-6-yl)methylamino]benzoyl]amino]pentanedioic acid; L-N-[p-[[(2-amino-5-formyl-5,6,7,8-tetrahydro-4-hydroxy-6-pteridinyl)methyl]amino]benzoyl]-Glutamic acid; 5-Formlyl-5,6,7,8-tetrahydrofolate,calcium salt; Leucovorin, calcium (1:1) salt, pentahydrate; Leucovorin, calcium (1:1) salt, (DL)-isomer; L(-)-5-Formyl-5,6,7,8-tetrahydrofolic acid; L(-)-5-Formyl-5,6,7,8-tetrahydrofolate; 5-Formyltetrahydropteroylglutamic acid; N5-Formyl-5,6,7,8-tetrahydrofolic acid; 5-Formyl-5,6,7,8-tetrahydrofolic acid; 5-Formyltetrahydropteroylglutamate; N5-Formyl-5,6,7,8-tetrahydrofolate; 5 Formyltetrahydropteroylglutamate; 5-FORMYL-5,6,7,8-TETRAHYDROFOLATE; 10-Formyl-7,8-dihydrofolic acid; (6R,S)-5-Formyltetrahydrofolate; Leucovorin, calcium (1:1) salt; N5-Formyltetrahydrofolic acid; 5-Formyltetrahydrofolic acid; Leucovorin, monosodium salt; N(5)-Formyltetrahydrofolate; 10-Formyl-7,8-dihydrofolate; Monosodium salt leucovorin; n5-formyltetrahydrofolate; 5-formyltetrahydrofolate; 5 Formyltetrahydrofolate; Leucovorin, (DL)-isomer; Leucovorin, (R)-isomer; Leucovorin, (D)-isomer; Leucovorin, calcium; Factor, citrovorum; Calcium leucovorin; Folinate, calcium; (6R)-Folinic acid; Citrovorum factor; Calcium folinate; Folinic acid-SF; Folinic acid SF; Levoleucovorin; Acid, folinic; Folinic acid; l-Leucovorin; Wellcovorin; Leukovorin; leucovorin; Welcovorin; Rescuvolin; Leukovorum; Folinate; Leucal; Folinic acid
数据库引用编号
21 个数据库交叉引用编号
- ChEBI: CHEBI:63606
- KEGG: C03479
- PubChem: 135398559
- PubChem: 143
- HMDB: HMDB0247218
- Metlin: METLIN595
- DrugBank: DB11596
- ChEMBL: CHEMBL1908841
- MeSH: Levoleucovorin
- foodb: FDB022689
- chemspider: 140
- CAS: 68538-85-2
- CAS: 58-05-9
- ChEBI: CHEBI:15640
- PubChem: 6294
- PDB-CCD: FFO
- PDB-CCD: FOZ
- 3DMET: B04899
- NIKKAJI: J9.322J
- medchemexpress: HY-17556
- KNApSAcK: 15640
分类词条
相关代谢途径
Reactome(0)
PlantCyc(0)
代谢反应
18 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(1)
- formylTHF biosynthesis II:
H+ + NAD+ + gly + tetrahydrofolate ⟶ 5,10-methylenetetrahydrofolate + CO2 + NADH + ammonia
WikiPathways(0)
Plant Reactome(0)
INOH(1)
- Folate metabolism ( Folate metabolism ):
6-Pyruvoyl-5,6,7,8-tetrahydro-pterin + NADPH ⟶ 5,6,7,8-Tetrahydro-biopterin + NADP+
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(16)
- Folate Metabolism:
5-Formiminotetrahydrofolic acid ⟶ 5,10-Methenyltetrahydrofolic acid + Ammonia
- Methotrexate Action Pathway:
5-Formiminotetrahydrofolic acid ⟶ 5,10-Methenyltetrahydrofolic acid + Ammonia
- Methylenetetrahydrofolate Reductase Deficiency (MTHFRD):
5-Formiminotetrahydrofolic acid ⟶ 5,10-Methenyltetrahydrofolic acid + Ammonia
- Folate Malabsorption, Hereditary:
5-Formiminotetrahydrofolic acid ⟶ 5,10-Methenyltetrahydrofolic acid + Ammonia
- Folate Metabolism:
5-Formiminotetrahydrofolic acid ⟶ 5,10-Methenyltetrahydrofolic acid + Ammonia
- Folate Malabsorption, Hereditary:
5-Formiminotetrahydrofolic acid ⟶ 5,10-Methenyltetrahydrofolic acid + Ammonia
- Methylenetetrahydrofolate Reductase Deficiency (MTHFRD):
5-Formiminotetrahydrofolic acid ⟶ 5,10-Methenyltetrahydrofolic acid + Ammonia
- Folate Malabsorption, Hereditary:
5-Formiminotetrahydrofolic acid ⟶ 5,10-Methenyltetrahydrofolic acid + Ammonia
- Folate Metabolism:
5-Formiminotetrahydrofolic acid ⟶ 5,10-Methenyltetrahydrofolic acid + Ammonia
- Folate Metabolism:
5-Formiminotetrahydrofolic acid ⟶ 5,10-Methenyltetrahydrofolic acid + Ammonia
- Folate Metabolism:
5-Formiminotetrahydrofolic acid ⟶ 5,10-Methenyltetrahydrofolic acid + Ammonia
- Folate Metabolism:
5-Formiminotetrahydrofolic acid ⟶ 5,10-Methenyltetrahydrofolic acid + Ammonia
- Methylenetetrahydrofolate Reductase Deficiency (MTHFRD):
5-Formiminotetrahydrofolic acid ⟶ 5,10-Methenyltetrahydrofolic acid + Ammonia
- One Carbon Pool by Folate:
S-Aminomethyldihydrolipoylprotein; + Tetrahydrofolic acid ⟶ 5,10-Methylene-THF + Ammonia + dihydrolipoylprotein
- One Carbon Pool by Folate I:
S-Aminomethyldihydrolipoylprotein; + Tetrahydrofolic acid ⟶ 5,10-Methylene-THF + Ammonia + dihydrolipoylprotein
- One Carbon Pool by Folate:
S-Aminomethyldihydrolipoylprotein; + Tetrahydrofolic acid ⟶ 5,10-Methylene-THF + Ammonia + dihydrolipoylprotein
PharmGKB(0)
4 个相关的物种来源信息
- 9606 - Homo sapiens: -
- 9606 - Homo sapiens: 10.1007/S11306-016-1051-4
- 3498 - Morus alba L.: -
- 33090 - Plants: -
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 Cirronis, E Novara, T Persiano, S Perlini, C A Locatelli. Bowel perforation due to methotrexate therapeutic error: an insidious adverse reaction.
European review for medical and pharmacological sciences.
2021 03; 25(5):2344-2347. doi:
10.26355/eurrev_202103_25273
. [PMID: 33755972] - Monica Lamberti, Stefania Porto, Silvia Zappavigna, Paola Stiuso, Virginia Tirino, Vincenzo Desiderio, Luigi Mele, Michele Caraglia. Levofolene modulates apoptosis induced by 5-fluorouracil through autophagy inhibition: clinical and occupational implications.
International journal of oncology.
2015 May; 46(5):1893-900. doi:
10.3892/ijo.2015.2904
. [PMID: 25709090] - Yvonne Wettergren, Helena Taflin, Elisabeth Odin, Karl Kodeda, Kristoffer Derwinger. A pharmacokinetic and pharmacodynamic investigation of Modufolin® compared to Isovorin® after single dose intravenous administration to patients with colon cancer: a randomized study.
Cancer chemotherapy and pharmacology.
2015 Jan; 75(1):37-47. doi:
10.1007/s00280-014-2611-9
. [PMID: 25342290] - Leon van Haandel, Mara L Becker, Todd D Williams, John F Stobaugh, J Steven Leeder. Comprehensive quantitative measurement of folate polyglutamates in human erythrocytes by ion pairing ultra-performance liquid chromatography/tandem mass spectrometry.
Rapid communications in mass spectrometry : RCM.
2012 Jul; 26(14):1617-30. doi:
10.1002/rcm.6268
. [PMID: 22693118] - Djeneb Camara, Cordelia Bisanz, Caroline Barette, Jeroen Van Daele, Esmare Human, Bernice Barnard, Dominique Van der Straeten, Christophe P Stove, Willy E Lambert, Roland Douce, Eric Maréchal, Lyn-Marie Birkholtz, Marie-France Cesbron-Delauw, Renaud Dumas, Fabrice Rébeillé. Inhibition of p-aminobenzoate and folate syntheses in plants and apicomplexan parasites by natural product rubreserine.
The Journal of biological chemistry.
2012 Jun; 287(26):22367-76. doi:
10.1074/jbc.m112.365833
. [PMID: 22577137] - Hyagriv N Simhan, Katherine P Himes, Raman Venkataramanan, Lisa M Bodnar. Maternal serum folate species in early pregnancy and lower genital tract inflammatory milieu.
American journal of obstetrics and gynecology.
2011 Jul; 205(1):61.e1-7. doi:
10.1016/j.ajog.2011.03.039
. [PMID: 21600548] - Svetlana Gerdes, Basma El Yacoubi, Marc Bailly, Ian K Blaby, Crysten E Blaby-Haas, Linda Jeanguenin, Aurora Lara-Núñez, Anne Pribat, Jeffrey C Waller, Andreas Wilke, Ross Overbeek, Andrew D Hanson, Valérie de Crécy-Lagard. Synergistic use of plant-prokaryote comparative genomics for functional annotations.
BMC genomics.
2011 Jun; 12 Suppl 1(?):S2. doi:
10.1186/1471-2164-12-s1-s2
. [PMID: 21810204] - Hironori Fujii, Hirotoshi Iihara, Koji Yasuda, Katsuhiko Matsuura, Takao Takahashi, Kazuhiro Yoshida, Yoshinori Itoh. Evaluation of efficacy and safety of generic levofolinate in patients who received colorectal cancer chemotherapy.
Medical oncology (Northwood, London, England).
2011 Jun; 28(2):488-93. doi:
10.1007/s12032-010-9487-2
. [PMID: 20354823] - Veronica E Ohrvik, Cornelia M Witthoft. Human folate bioavailability.
Nutrients.
2011 04; 3(4):475-90. doi:
10.3390/nu3040475
. [PMID: 22254106] - M Hogeveen, M den Heijer, Y Schonbeck, M Ijland, D van Oppenraaij, J K Gunnewiek, H J Blom. The effect of folinic acid supplementation on homocysteine concentrations in newborns.
European journal of clinical nutrition.
2010 Nov; 64(11):1266-71. doi:
10.1038/ejcn.2010.155
. [PMID: 20823897] - Yi Zhang, Kehan Sun, Francisco J Sandoval, Katherine Santiago, Sanja Roje. One-carbon metabolism in plants: characterization of a plastid serine hydroxymethyltransferase.
The Biochemical journal.
2010 Aug; 430(1):97-105. doi:
10.1042/bj20100566
. [PMID: 20518745] - Harry Martin, Daniel Comeskey, Robert M Simpson, William A Laing, Tony K McGhie. Quantification of folate in fruits and vegetables: A fluorescence-based homogeneous assay.
Analytical biochemistry.
2010 Jul; 402(2):137-45. doi:
10.1016/j.ab.2010.03.032
. [PMID: 20361923] - Ersin Selcuk Unal, Rongbao Zhao, I David Goldman. Role of the glutamate 185 residue in proton translocation mediated by the proton-coupled folate transporter SLC46A1.
American journal of physiology. Cell physiology.
2009 Jul; 297(1):C66-74. doi:
10.1152/ajpcell.00096.2009
. [PMID: 19403800] - Hong-Yang Zhang, Guo-An Luo, Qiong-Lin Liang, Yong Wang, Hui-Hua Yang, Yi-Ming Wang, Xiao-Ying Zheng, Xin-Ming Song, Gong Chen, Ting Zhang, Jian-Xin Wu. Neural tube defects and disturbed maternal folate- and homocysteine-mediated one-carbon metabolism.
Experimental neurology.
2008 Aug; 212(2):515-21. doi:
10.1016/j.expneurol.2008.04.044
. [PMID: 18589417] - Veerle De Brouwer, Guo-Fang Zhang, Sergei Storozhenko, Dominique Van Der Straeten, Willy E Lambert. pH stability of individual folates during critical sample preparation steps in prevision of the analysis of plant folates.
Phytochemical analysis : PCA.
2007 Nov; 18(6):496-508. doi:
10.1002/pca.1006
. [PMID: 17624887] - Shrikanta Chattopadhyay, Roni Tamari, Sang H Min, Rongbao Zhao, Eugenia Tsai, I David Goldman. Commentary: a case for minimizing folate supplementation in clinical regimens with pemetrexed based on the marked sensitivity of the drug to folate availability.
The oncologist.
2007 Jul; 12(7):808-15. doi:
10.1634/theoncologist.12-7-808
. [PMID: 17673612] - Priyanka Sharma, R D Senthilkumar, Vani Brahmachari, Elayanambi Sundaramoorthy, Anubha Mahajan, Amitabh Sharma, Shantanu Sengupta. Mining literature for a comprehensive pathway analysis: a case study for retrieval of homocysteine related genes for genetic and epigenetic studies.
Lipids in health and disease.
2006 Jan; 5(?):1. doi:
10.1186/1476-511x-5-1
. [PMID: 16430779] - 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] - Aymeric Goyer, Eva Collakova, Rocío Díaz de la Garza, Eoin P Quinlivan, Jerry Williamson, Jesse F Gregory, Yair Shachar-Hill, Andrew D Hanson. 5-Formyltetrahydrofolate is an inhibitory but well tolerated metabolite in Arabidopsis leaves.
The Journal of biological chemistry.
2005 Jul; 280(28):26137-42. doi:
10.1074/jbc.m503106200
. [PMID: 15888445] - Guo-Fang Zhang, Sergei Storozhenko, Dominique Van Der Straeten, Willy E Lambert. Investigation of the extraction behavior of the main monoglutamate folates from spinach by liquid chromatography-electrospray ionization tandem mass spectrometry.
Journal of chromatography. A.
2005 Jun; 1078(1-2):59-66. doi:
10.1016/j.chroma.2005.04.085
. [PMID: 16007982] - Johan D M Patring, Jelena A Jastrebova, Sofia B Hjortmo, Thomas A Andlid, I Margaretha Jägerstad. Development of a simplified method for the determination of folates in baker's yeast by HPLC with ultraviolet and fluorescence detection.
Journal of agricultural and food chemistry.
2005 Apr; 53(7):2406-11. doi:
10.1021/jf048083g
. [PMID: 15796570] - Rongbao Zhao, Shubing Zhang, Marie Hanscom, Shrikanta Chattopadhyay, I David Goldman. Loss of reduced folate carrier function and folate depletion result in enhanced pemetrexed inhibition of purine synthesis.
Clinical cancer research : an official journal of the American Association for Cancer Research.
2005 Feb; 11(3):1294-301. doi:
. [PMID: 15709201]
- Rongbao Zhao, Yanhua Wang, Feng Gao, I David Goldman. Residues 45 and 404 in the murine reduced folate carrier may interact to alter carrier binding and mobility.
Biochimica et biophysica acta.
2003 Jun; 1613(1-2):49-56. doi:
10.1016/s0005-2736(03)00136-6
. [PMID: 12832086] - Achim Freisleben, Peter Schieberle, Michael Rychlik. Specific and sensitive quantification of folate vitamers in foods by stable isotope dilution assays using high-performance liquid chromatography-tandem mass spectrometry.
Analytical and bioanalytical chemistry.
2003 May; 376(2):149-56. doi:
10.1007/s00216-003-1844-y
. [PMID: 12698226] - Qilin Song, Charles K Singleton. Mitochondria from cultured cells derived from normal and thiamine-responsive megaloblastic anemia individuals efficiently import thiamine diphosphate.
BMC biochemistry.
2002 Apr; 3(?):8. doi:
10.1186/1471-2091-3-8
. [PMID: 12014993] - Henning Schulze-Bergkamen, Ivan Zuna, Andreas Teufel, Wolfgang Stremmel, Jochen Rudi. Treatment of advanced gastric cancer with etoposide, folinic acid, and fluorouracil in the clinical setting: efficacy of therapy and value of serum tumor markers.
Medical oncology (Northwood, London, England).
2002; 19(1):43-53. doi:
10.1385/mo:19:1:43
. [PMID: 12025890] - H R Thompson, G M Jones, M R Narkewicz. Ontogeny of hepatic enzymes involved in serine- and folate-dependent one-carbon metabolism in rabbits.
American journal of physiology. Gastrointestinal and liver physiology.
2001 May; 280(5):G873-8. doi:
10.1152/ajpgi.2001.280.5.g873
. [PMID: 11292595] - X Liu, D M Szebenyi, M C Anguera, D J Thiel, P J Stover. Lack of catalytic activity of a murine mRNA cytoplasmic serine hydroxymethyltransferase splice variant: evidence against alternative splicing as a regulatory mechanism.
Biochemistry.
2001 Apr; 40(16):4932-9. doi:
10.1021/bi002598t
. [PMID: 11305908] - R L Schilsky, M J Ratain. Clinical pharmacokinetics of high-dose leucovorin calcium after intravenous and oral administration.
Journal of the National Cancer Institute.
1990 Sep; 82(17):1411-5. doi:
10.1093/jnci/82.17.1411
. [PMID: 2388292] - H Wilke, P Preusser, U Fink, W Achterrath, H J Meyer, M Stahl, L Lenaz, J Meyer, J R Siewert, H Geerlings. New developments in the treatment of gastric carcinoma.
Seminars in oncology.
1990 Feb; 17(1 Suppl 2):61-70. doi:
. [PMID: 2305269]
- T Asakawa, C Johnson, J Ruiz, I Scheinbaum, T R Russell, R Ho, E W Sutherland. Activation by 'feedback regulator' and some properties of guanylate cyclase of plasma membrane of rat epididymal fat cells.
Biochemical and biophysical research communications.
1976 Oct; 72(4):1335-42. doi:
10.1016/s0006-291x(76)80161-1
. [PMID: 11790]