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CHEBI ONTOLOGY - ANNOTATIONS

The Chemical Entities of Biological Interest (ChEBI) ontology is downloaded weekly from EMBL-EBI at http://www.ebi.ac.uk/chebi/. The data is made available under the Creative Commons License (CC BY 3.0, http://creativecommons.org/licenses/by/3.0/). For more information see: Degtyarenko et al. (2008) ChEBI: a database and ontology for chemical entities of biological interest. Nucleic Acids Res. 36, D344–D350.

Term:5-formyltetrahydrofolic acid
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Accession:CHEBI:15640 term browser browse the term
Definition:A formyltetrahydrofolic acid in which the formyl group is located at position 5.
Synonyms:exact_synonym: N-[4-({[2-amino-5-formyl-4-oxo-3,4,5,6,7,8-hexahydropteridin-6-yl]methyl}amino)benzoyl]-L-glutamic acid
 related_synonym: (5-formyl-5,6,7,8-tetrahydropteroyl)glutamate;   10-Formyl-7,8-dihydrofolic acid;   5-Formyl-5,6,7,8-tetrahydrofolic acid;   5-Formyl-5,6,7,8-tetrahydropteroyl-L-glutamic acid;   5-Formyltetrahydrofolate;   Acide folinique;   Folinic acid;   Formula=C20H23N7O7;   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)/t12?,13-/m0/s1;   InChIKey=VVIAGPKUTFNRDU-ABLWVSNPSA-N;   L(-)-5-Formyl-5,6,7,8-tetrahydrofolic acid;   Leucovorin;   Leucovorinum;   N-(5-formyl-5,6,7,8-tetrahydropteroyl)-L-glutamic acid;   N5-Formyl-5,6,7,8-tetrahydrofolic acid;   N5-Formyltetrahydrofolic acid;   SMILES=[H]C(=O)N1C(CNc2ccc(cc2)C(=O)N[C@@H](CCC(O)=O)C(O)=O)CNc2nc(N)[nH]c(=O)c12;   folinate
 alt_id: CHEBI:12127;   CHEBI:18607;   CHEBI:2057
 xref: CAS:58-05-9;   DrugBank:DB03256;   Drug_Central:1232;   KEGG:C03479;   KEGG:D07986;   LINCS:LSM-5146
 xref_mesh: MESH:D002955
 xref: Reaxys:101688;   Wikipedia:Folinic_acid
 cyclic_relationship: is_conjugate_acid_of CHEBI:65340


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5-formyltetrahydrofolic acid term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Abcc2 ATP binding cassette subfamily C member 2 multiple interactions EXP Leucovorin inhibits the reaction [Methotrexate results in decreased expression of ABCC2 protein] CTD PMID:16925582 NCBI chr 1:263,554,426...263,612,556
Ensembl chr 1:263,554,453...263,613,252
JBrowse link
G Alb albumin multiple interactions ISO [Leucovorin co-treated with Cisplatin co-treated with Fluorouracil] results in decreased expression of ALB protein CTD PMID:20180123 NCBI chr14:19,176,275...19,191,793
Ensembl chr14:19,176,277...19,191,863
JBrowse link
G Angptl2 angiopoietin-like 2 multiple interactions ISO ANGPTL2 mRNA results in increased susceptibility to [Leucovorin co-treated with Fluorouracil co-treated with irinotecan] CTD PMID:17327601 NCBI chr 3:12,262,822...12,292,665
Ensembl chr 3:12,262,822...12,292,663
JBrowse link
G Arl6ip5 ADP-ribosylation factor like GTPase 6 interacting protein 5 multiple interactions ISO ARL6IP5 protein affects the susceptibility to [Fluorouracil co-treated with Leucovorin co-treated with Cisplatin]; ARL6IP5 protein affects the susceptibility to [Fluorouracil co-treated with Leucovorin co-treated with oxaliplatin] CTD PMID:22452940 NCBI chr 4:129,574,363...129,598,240
Ensembl chr 4:129,574,264...129,598,915
JBrowse link
G Atp5po ATP synthase peripheral stalk subunit OSCP multiple interactions ISO ATP5PO mRNA results in increased susceptibility to [Leucovorin co-treated with Fluorouracil co-treated with irinotecan] CTD PMID:17327601 NCBI chr11:32,081,606...32,087,918
Ensembl chr11:32,081,574...32,088,002
JBrowse link
G Axin2 axin 2 multiple interactions EXP [Methotrexate co-treated with Leucovorin] results in increased expression of AXIN2 mRNA CTD PMID:25187349 NCBI chr10:97,212,483...97,238,824
Ensembl chr10:97,212,432...97,239,642
JBrowse link
G Bglap bone gamma-carboxyglutamate protein multiple interactions EXP [Methotrexate co-treated with Leucovorin] results in increased expression of BGLAP mRNA CTD PMID:25187349 NCBI chr 2:187,741,770...187,748,445
Ensembl chr 2:187,741,770...187,742,747
JBrowse link
G Boll boule homolog, RNA binding protein multiple interactions ISO BOLL mRNA results in increased susceptibility to [Leucovorin co-treated with Fluorouracil co-treated with irinotecan] CTD PMID:17327601 NCBI chr 9:61,836,517...61,975,640
Ensembl chr 9:64,480,031...64,573,660
Ensembl chr 9:64,480,031...64,573,660
JBrowse link
G Casp3 caspase 3 multiple interactions ISO [10-hydroxycamptothecin co-treated with Fluorouracil co-treated with Leucovorin] results in increased activity of CASP3 protein CTD PMID:12934351 NCBI chr16:48,845,011...48,863,249
Ensembl chr16:48,845,012...48,863,204
JBrowse link
G Ccnd1 cyclin D1 multiple interactions EXP [Methotrexate co-treated with Leucovorin] results in increased expression of CCND1 mRNA CTD PMID:25187349 NCBI chr 1:218,090,750...218,100,447
Ensembl chr 1:218,090,750...218,100,325
JBrowse link
G Ccne1 cyclin E1 multiple interactions ISO [Leucovorin co-treated with Fluorouracil] results in increased expression of CCNE1 mRNA CTD PMID:15342418 NCBI chr 1:94,485,830...94,495,112
Ensembl chr 1:94,485,832...94,494,980
JBrowse link
G Cdc45 cell division cycle 45 multiple interactions ISO [Leucovorin co-treated with Fluorouracil] results in increased expression of CDC45 mRNA CTD PMID:15342418 NCBI chr11:86,328,785...86,354,099
Ensembl chr11:86,329,012...86,358,453
JBrowse link
G Cdc6 cell division cycle 6 multiple interactions ISO [Leucovorin co-treated with Fluorouracil] results in increased expression of CDC6 mRNA CTD PMID:15342418 NCBI chr10:86,819,477...86,833,301
Ensembl chr10:86,819,472...86,833,402
JBrowse link
G Cdk1 cyclin-dependent kinase 1 multiple interactions ISO [Leucovorin co-treated with Fluorouracil] results in increased expression of CDK1 mRNA CTD PMID:15342418 NCBI chr20:20,576,341...20,591,510
Ensembl chr20:20,576,377...20,591,549
JBrowse link
G Cdk2 cyclin dependent kinase 2 multiple interactions ISO [Leucovorin co-treated with Fluorouracil] results in increased expression of CDK2 mRNA CTD PMID:15342418 NCBI chr 7:3,124,953...3,132,533
Ensembl chr 7:3,124,954...3,132,457
JBrowse link
G Cdkn1a cyclin-dependent kinase inhibitor 1A multiple interactions ISO [Leucovorin co-treated with Fluorouracil] results in increased expression of CDKN1A mRNA CTD PMID:15342418 NCBI chr20:6,348,422...6,358,864
Ensembl chr20:6,351,458...6,358,864
JBrowse link
G Ctnnb1 catenin beta 1 multiple interactions EXP [Methotrexate co-treated with Leucovorin] results in increased expression of CTNNB1 protein CTD PMID:25187349 NCBI chr 8:129,601,511...129,628,378
Ensembl chr 8:129,617,812...129,627,372
JBrowse link
G Cyp11a1 cytochrome P450, family 11, subfamily a, polypeptide 1 multiple interactions EXP Leucovorin affects the reaction [Methotrexate results in decreased expression of CYP11A1 mRNA]; Leucovorin affects the reaction [Methotrexate results in decreased expression of CYP11A1 protein] CTD PMID:21213337 NCBI chr 8:62,798,317...62,809,848
Ensembl chr 8:62,779,875...62,809,893
JBrowse link
G Dhfr dihydrofolate reductase multiple interactions
increases expression
ISO Leucovorin inhibits the reaction [DHFR gene mutant form results in decreased abundance of Folic Acid]
Leucovorin results in increased expression of DHFR protein
CTD PMID:16712799, PMID:21310277 NCBI chr 2:21,931,887...21,958,927
Ensembl chr 2:21,931,493...21,962,453
JBrowse link
G Dpyd dihydropyrimidine dehydrogenase multiple interactions ISO [Leucovorin co-treated with Fluorouracil] results in decreased activity of DPYD protein CTD PMID:7503095 NCBI chr 2:221,823,692...222,694,627
Ensembl chr 2:221,823,687...222,694,627
JBrowse link
G Drd5 dopamine receptor D5 multiple interactions ISO DRD5 mRNA results in increased susceptibility to [Leucovorin co-treated with Fluorouracil co-treated with irinotecan] CTD PMID:17327601 NCBI chr14:77,220,579...77,222,006
Ensembl chr14:77,220,579...77,222,006
JBrowse link
G Edn1 endothelin 1 increases expression ISO Leucovorin results in increased expression of EDN1 mRNA; Leucovorin results in increased expression of EDN1 protein CTD PMID:16925845 NCBI chr17:22,136,814...22,143,745
Ensembl chr17:22,137,324...22,143,324
JBrowse link
G Eml2 EMAP like 2 multiple interactions ISO EML2 mRNA results in increased susceptibility to [Leucovorin co-treated with Fluorouracil co-treated with irinotecan] CTD PMID:17327601 NCBI chr 1:80,087,684...80,118,784
Ensembl chr 1:80,087,684...80,119,012
JBrowse link
G Ercc1 ERCC excision repair 1, endonuclease non-catalytic subunit multiple interactions ISO ERCC1 gene SNP affects the susceptibility to [Fluorouracil co-treated with Leucovorin co-treated with oxaliplatin] CTD PMID:17401013 NCBI chr 1:80,256,973...80,268,198
Ensembl chr 1:80,256,973...80,268,198
JBrowse link
G Ercc2 ERCC excision repair 2, TFIIH core complex helicase subunit multiple interactions ISO ERCC2 gene SNP affects the susceptibility to [Fluorouracil co-treated with Leucovorin co-treated with oxaliplatin] CTD PMID:17401013 NCBI chr 1:80,293,574...80,307,334
Ensembl chr 1:80,293,566...80,307,344
JBrowse link
G F8 coagulation factor VIII multiple interactions ISO F8 mRNA results in increased susceptibility to [Leucovorin co-treated with Fluorouracil co-treated with irinotecan] CTD PMID:17327601 NCBI chr18:367,862...399,242
Ensembl chr18:367,862...399,242
JBrowse link
G Fabp4 fatty acid binding protein 4 multiple interactions EXP Leucovorin inhibits the reaction [Methotrexate results in increased expression of FABP4 protein] CTD PMID:25187349 NCBI chr 2:93,792,666...93,797,267
Ensembl chr 2:93,792,601...93,797,305
JBrowse link
G Folr1 folate receptor alpha multiple interactions ISO FOLR1 protein affects the reaction [Leucovorin results in increased phosphorylation of STAT3 protein] CTD PMID:25841994 NCBI chr 1:166,934,457...166,945,864
Ensembl chr 1:166,934,460...166,943,592
JBrowse link
G Fshb follicle stimulating hormone subunit beta multiple interactions EXP Leucovorin affects the reaction [Methotrexate results in increased expression of FSHB protein] CTD PMID:21213337 NCBI chr 3:98,088,321...98,092,131
Ensembl chr 3:98,088,324...98,092,131
JBrowse link
G G6pd glucose-6-phosphate dehydrogenase multiple interactions EXP Leucovorin inhibits the reaction [Methotrexate results in decreased activity of G6PD protein] CTD PMID:21213337 NCBI chr  X:156,274,800...156,293,935
Ensembl chr  X:156,274,800...156,293,926
JBrowse link
G Hand2 heart and neural crest derivatives expressed 2 increases expression ISO Leucovorin results in increased expression of HAND2 mRNA; Leucovorin results in increased expression of HAND2 protein CTD PMID:16925845 NCBI chr16:36,371,489...36,373,551
Ensembl chr16:36,371,489...36,373,546
JBrowse link
G Hspb1 heat shock protein family B (small) member 1 multiple interactions ISO HSPB1 protein affects the susceptibility to [Cisplatin co-treated with Fluorouracil co-treated with Leucovorin] CTD PMID:19088045 NCBI chr12:23,839,390...23,841,051
Ensembl chr12:23,839,399...23,841,049
JBrowse link
G Il1b interleukin 1 beta multiple interactions ISO Leucovorin inhibits the reaction [Methotrexate results in increased expression of IL1B mRNA] CTD PMID:24444433 NCBI chr 3:121,876,256...121,882,637
Ensembl chr 3:121,876,263...121,882,726
JBrowse link
G Il6 interleukin 6 multiple interactions ISO Leucovorin inhibits the reaction [Methotrexate results in increased expression of IL6 mRNA] CTD PMID:24444433 NCBI chr 4:3,043,231...3,047,807
Ensembl chr 4:3,043,231...3,047,807
JBrowse link
G Il6st interleukin 6 signal transducer multiple interactions ISO IL6ST protein affects the reaction [Leucovorin results in increased phosphorylation of STAT3 protein] CTD PMID:25841994 NCBI chr 2:44,279,199...44,319,427
Ensembl chr 2:44,289,393...44,314,944
JBrowse link
G Lef1 lymphoid enhancer binding factor 1 multiple interactions EXP [Methotrexate co-treated with Leucovorin] results in increased expression of LEF1 mRNA CTD PMID:25187349 NCBI chr 2:236,232,115...236,345,061
Ensembl chr 2:236,233,239...236,345,056
JBrowse link
G Lgals8 galectin 8 multiple interactions ISO LGALS8 mRNA results in increased susceptibility to [Leucovorin co-treated with Fluorouracil co-treated with irinotecan] CTD PMID:17327601 NCBI chr17:66,487,451...66,515,316
Ensembl chr17:66,487,457...66,511,870
JBrowse link
G Lhb luteinizing hormone subunit beta multiple interactions EXP Leucovorin affects the reaction [Methotrexate results in increased expression of LHB protein] CTD PMID:21213337 NCBI chr 1:101,409,992...101,413,725
Ensembl chr 1:101,410,019...101,413,724
JBrowse link
G LOC102548162 zinc finger protein 582-like multiple interactions ISO ZNF582 mRNA results in increased susceptibility to [Leucovorin co-treated with Fluorouracil co-treated with irinotecan] CTD PMID:17327601 NCBI chr 1:71,206,073...71,228,209 JBrowse link
G Mat2a methionine adenosyltransferase 2A multiple interactions ISO Leucovorin inhibits the reaction [Methotrexate results in decreased expression of MAT2A mRNA] CTD PMID:22193356 NCBI chr 4:100,297,478...100,303,047
Ensembl chr 4:100,296,075...100,303,080
JBrowse link
G Mthfr methylenetetrahydrofolate reductase multiple interactions ISO MTHFR gene polymorphism results in increased susceptibility to [Fluorouracil co-treated with Leucovorin] CTD PMID:18633250 NCBI chr 5:164,844,642...164,864,360
Ensembl chr 5:164,845,925...164,860,910
JBrowse link
G Pparg peroxisome proliferator-activated receptor gamma multiple interactions EXP [Methotrexate co-treated with Leucovorin] results in increased expression of PPARG mRNA; [Methotrexate co-treated with Leucovorin] results in increased expression of PPARG protein CTD PMID:25187349 NCBI chr 4:147,274,055...147,399,383
Ensembl chr 4:147,274,107...147,399,380
JBrowse link
G Serpine2 serpin family E member 2 multiple interactions ISO SERPINE2 mRNA results in increased susceptibility to [Leucovorin co-treated with Fluorouracil co-treated with irinotecan] CTD PMID:17327601 NCBI chr 9:85,560,852...85,629,410
Ensembl chr 9:85,560,863...85,626,094
JBrowse link
G Sfrp1 secreted frizzled-related protein 1 multiple interactions EXP Leucovorin inhibits the reaction [Methotrexate results in increased expression of SFRP1 mRNA]; Leucovorin inhibits the reaction [Methotrexate results in increased expression of SFRP1 protein] CTD PMID:25187349 NCBI chr16:73,372,007...73,410,777
Ensembl chr16:73,372,007...73,410,777
JBrowse link
G Slc19a1 solute carrier family 19 member 1 multiple interactions ISO Leucovorin inhibits the reaction [SLC19A1 protein results in increased transport of Methotrexate] CTD PMID:21879757 NCBI chr20:12,334,675...12,354,517
Ensembl chr20:12,334,676...12,352,377
JBrowse link
G Slc22a6 solute carrier family 22 member 6 multiple interactions
increases uptake
EXP
ISO
Leucovorin inhibits the reaction [Methotrexate results in decreased expression of SLC22A6 protein]
SLC22A6 protein results in increased uptake of Leucovorin
CTD PMID:16098483, PMID:16925582 NCBI chr 1:224,824,809...224,833,284
Ensembl chr 1:224,824,799...224,833,259
JBrowse link
G Slc22a8 solute carrier family 22 member 8 multiple interactions
increases uptake
EXP
ISO
Leucovorin inhibits the reaction [Methotrexate results in decreased expression of SLC22A8 protein]
SLC22A8 protein results in increased uptake of Leucovorin
CTD PMID:16098483, PMID:16925582 NCBI chr 1:224,799,444...224,818,482
Ensembl chr 1:224,800,252...224,818,482
JBrowse link
G Slc46a1 solute carrier family 46 member 1 decreases activity
multiple interactions
ISO Leucovorin results in decreased activity of SLC46A1 protein
Leucovorin inhibits the reaction [SLC46A1 protein results in increased transport of Folic Acid]
CTD PMID:17475902 NCBI chr10:65,728,508...65,741,708
Ensembl chr10:65,733,991...65,740,828
JBrowse link
G Sp7 Sp7 transcription factor multiple interactions EXP [Methotrexate co-treated with Leucovorin] results in increased expression of SP7 mRNA CTD PMID:25187349 NCBI chr 7:143,957,316...143,967,488
Ensembl chr 7:143,958,858...143,967,484
JBrowse link
G Star steroidogenic acute regulatory protein multiple interactions EXP Leucovorin affects the reaction [Methotrexate results in decreased expression of STAR mRNA]; Leucovorin affects the reaction [Methotrexate results in decreased expression of STAR protein] CTD PMID:21213337 NCBI chr16:71,036,204...71,040,847
Ensembl chr16:71,036,204...71,040,847
JBrowse link
G Stat3 signal transducer and activator of transcription 3 multiple interactions ISO FOLR1 protein affects the reaction [Leucovorin results in increased phosphorylation of STAT3 protein]; IL6ST protein affects the reaction [Leucovorin results in increased phosphorylation of STAT3 protein]; Leucovorin results in increased activity of and results in increased phosphorylation of STAT3 protein CTD PMID:25841994 NCBI chr10:88,790,401...88,842,263
Ensembl chr10:88,790,408...88,842,233
JBrowse link
G Tymp thymidine phosphorylase multiple interactions ISO TYMP mRNA affects the susceptibility to [irinotecan co-treated with Fluorouracil co-treated with Leucovorin] CTD PMID:17454858 NCBI chr 7:130,342,481...130,347,845
Ensembl chr 7:130,342,483...130,347,587
JBrowse link
G Tyms thymidylate synthetase multiple interactions ISO [arsenic trioxide co-treated with Fluorouracil co-treated with Leucovorin] results in decreased expression of TYMS mRNA; TYMS gene polymorphism results in increased susceptibility to [Leucovorin co-treated with Fluorouracil co-treated with Cisplatin co-treated with Paclitaxel]; TYMS mRNA affects the susceptibility to [irinotecan co-treated with Fluorouracil co-treated with Leucovorin]; TYMS promoter polymorphism results in increased susceptibility to [Fluorouracil co-treated with Leucovorin co-treated with oxaliplatin co-treated with docetaxel]; TYMS protein affects the susceptibility to [Fluorouracil co-treated with Leucovorin]
Leucovorin promotes the reaction [Fluorouracil results in decreased expression of TYMS]
CTD PMID:9050858, PMID:16424979, PMID:17454858, PMID:18676755, PMID:19074750, PMID:20501625 NCBI chr 9:121,918,875...121,931,564
Ensembl chr 9:121,918,947...121,931,564
JBrowse link
G Wnt10b Wnt family member 10B multiple interactions EXP [Methotrexate co-treated with Leucovorin] results in increased expression of WNT10B mRNA CTD PMID:25187349 NCBI chr 7:140,448,284...140,466,159
Ensembl chr 7:140,448,465...140,454,268
JBrowse link
G Xrcc1 X-ray repair cross complementing 1 multiple interactions ISO XRCC1 protein affects the susceptibility to [Fluorouracil co-treated with Leucovorin co-treated with Cisplatin]; XRCC1 protein affects the susceptibility to [Fluorouracil co-treated with Leucovorin co-treated with oxaliplatin] CTD PMID:22452940 NCBI chr 1:81,412,635...81,441,680
Ensembl chr 1:81,413,353...81,441,678
JBrowse link
G Zfp637 zinc finger protein 637 multiple interactions ISO ZNF32 mRNA results in increased susceptibility to [Leucovorin co-treated with Fluorouracil co-treated with irinotecan] CTD PMID:17327601 NCBI chr 4:149,857,127...149,882,828
Ensembl chr 4:149,877,889...149,882,824
JBrowse link
G Zrsr2 zinc finger (CCCH type), RNA binding motif and serine/arginine rich 2 multiple interactions ISO ZRSR2 mRNA results in increased susceptibility to [Leucovorin co-treated with Fluorouracil co-treated with irinotecan] CTD PMID:17327601 NCBI chr  X:32,304,707...32,327,419
Ensembl chr  X:32,304,757...32,328,364
JBrowse link

Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19785
    role 19732
      biological role 19732
        biochemical role 19281
          metabolite 19262
            prokaryotic metabolite 18356
              bacterial metabolite 18356
                Escherichia coli metabolite 18260
                  5-formyltetrahydrofolic acid 57
                    (6S)-5-formyltetrahydrofolic acid 0
Path 2
Term Annotations click to browse term
  CHEBI ontology 19785
    subatomic particle 19782
      composite particle 19782
        hadron 19782
          baryon 19782
            nucleon 19782
              atomic nucleus 19782
                atom 19782
                  main group element atom 19670
                    p-block element atom 19670
                      carbon group element atom 19572
                        carbon atom 19561
                          organic molecular entity 19561
                            organic group 18493
                              organic divalent group 18486
                                organodiyl group 18486
                                  carbonyl group 18389
                                    carbonyl compound 18389
                                      carboxylic acid 18060
                                        amino acid 14072
                                          alpha-amino acid 11539
                                            L-alpha-amino acid 11374
                                              glutamine family amino acid 10243
                                                L-glutamic acid 10190
                                                  L-glutamic acid derivative 9354
                                                    folic acids 9354
                                                      tetrahydrofolic acid 66
                                                        formyltetrahydrofolic acid 58
                                                          5-formyltetrahydrofolic acid 57
                                                            (6S)-5-formyltetrahydrofolic acid 0
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RGD is funded by grant HL64541 from the National Heart, Lung, and Blood Institute on behalf of the NIH.