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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:dicoumarol
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Accession:CHEBI:4513 term browser browse the term
Definition:A hydroxycoumarin that is methane in which two hydrogens have each been substituted by a 4-hydroxycoumarin-3-yl group. Related to warfarin, it has been used as an anticoagulant.
Synonyms:exact_synonym: 3,3'-methanediylbis(4-hydroxy-2H-chromen-2-one)
 related_synonym: 3,3'-methylen-bis(4-hydroxy-cumarin);   3,3'-methylene-bis(4-hydroxycoumarine);   3,3'-methylenebis(4-hydroxy-1,2-benzopyrone);   3,3'-methylenebis(4-hydroxy-2H-1-benzopyran-2-one);   3,3'-methylenebis(4-hydroxycoumarin);   Formula=C19H12O6;   InChI=1S/C19H12O6/c20-16-10-5-1-3-7-14(10)24-18(22)12(16)9-13-17(21)11-6-2-4-8-15(11)25-19(13)23/h1-8,20-21H,9H2;   InChIKey=DOBMPNYZJYQDGZ-UHFFFAOYSA-N;   SMILES=Oc1c(Cc2c(O)c3ccccc3oc2=O)c(=O)oc2ccccc12;   bis(4-hydroxycoumarin-3-yl)methane;   bis-3,3'-(4-hydroxycoumarinyl)methane;   bis-hydroxycoumarin;   di-(4-hydroxy-3-coumarinyl)methane;   dicoumarolum;   dicumarol
 alt_id: CHEBI:469386
 xref: Beilstein:335444;   CAS:66-76-2;   DrugBank:DB00266;   Drug_Central:867;   KEGG:C00796;   KEGG:D03798;   KNApSAcK:C00002467;   LINCS:LSM-5884
 xref_mesh: MESH:D001728
 xref: PMID:15639223;   PMID:16700548;   PMID:18347135;   PMID:19583730;   PMID:20480521;   PMID:28166217;   PMID:6033758;   Wikipedia:Dicumarol


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dicoumarol term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Akr1c1 aldo-keto reductase family 1, member C1 decreases activity EXP Dicumarol results in decreased activity of AKR1C6 protein CTD PMID:16788056 NCBI chr17:65,810,474...65,837,385
Ensembl chr17:65,810,475...65,837,326 		JBrowse link
G Alb albumin affects binding ISO Dicumarol binds to ALB protein CTD PMID:62049 NCBI chr14:17,607,397...17,622,814
Ensembl chr14:17,607,381...17,622,836 		JBrowse link
G Atm ATM serine/threonine kinase multiple interactions ISO Dicumarol inhibits the reaction [2,5-diaziridinyl-3-(hydroxymethyl)-6-methyl-1,4-benzoquinone analog results in increased expression of ATM protein modified form] CTD PMID:26630137 NCBI chr 8:53,828,741...53,932,773
Ensembl chr 8:53,831,093...53,932,437 		JBrowse link
G Casp3 caspase 3 multiple interactions EXP
ISO		 [aminochrome 1 co-treated with Dicumarol] results in increased activity of CASP3 protein; Dicumarol promotes the reaction [Doxorubicin results in increased activity of CASP3 protein]; Progesterone inhibits the reaction [Dicumarol promotes the reaction [Doxorubicin results in increased activity of CASP3 protein]]
Dicumarol inhibits the reaction [2,5-diaziridinyl-3-(hydroxymethyl)-6-methyl-1,4-benzoquinone analog results in decreased expression of CASP3 protein]		 CTD PMID:21427056 PMID:21947872 PMID:26630137 NCBI chr16:45,662,910...45,681,171
Ensembl chr16:45,662,910...45,684,648 		JBrowse link
G Cat catalase decreases response to substance
multiple interactions		 ISO
EXP		 CAT protein results in decreased susceptibility to Dicumarol
[Dopamine co-treated with Dicumarol] results in increased expression of CAT mRNA		 CTD PMID:11299314 PMID:17040906 NCBI chr 3:89,842,393...89,874,577
Ensembl chr 3:89,842,399...89,874,478 		JBrowse link
G Cd86 CD86 molecule multiple interactions ISO [Dicumarol results in decreased activity of NQO1 protein] inhibits the reaction [Eugenol results in increased expression of CD86 protein] CTD PMID:21742781 NCBI chr11:64,142,193...64,200,816
Ensembl chr11:64,163,828...64,200,818 		JBrowse link
G Cdkn1a cyclin-dependent kinase inhibitor 1A multiple interactions ISO Dicumarol inhibits the reaction [diaziquone results in increased expression of CDKN1A mRNA]; Dicumarol inhibits the reaction [Nicotinamide Mononucleotide inhibits the reaction [Hydrogen Peroxide results in increased expression of CDKN1A protein]]; Dicumarol inhibits the reaction [RB1CC1 protein results in increased expression of CDKN1A protein] CTD PMID:9343371 PMID:16061648 PMID:37640247 NCBI chr20:7,149,177...7,159,727
Ensembl chr20:7,149,217...7,159,585 		JBrowse link
G Cdkn2a cyclin-dependent kinase inhibitor 2A multiple interactions ISO Dicumarol inhibits the reaction [Nicotinamide Mononucleotide inhibits the reaction [Hydrogen Peroxide results in increased expression of CDKN2A protein]] CTD PMID:37640247 NCBI chr 5:103,984,949...103,992,143
Ensembl chr 5:103,984,949...104,003,149 		JBrowse link
G Cycs cytochrome c, somatic multiple interactions EXP [aminochrome 1 co-treated with Dicumarol] affects the localization of CYCS protein CTD PMID:21427056 NCBI chr 4:79,651,894...79,653,994
Ensembl chr 4:79,651,378...79,654,054
Ensembl chr18:79,651,378...79,654,054 		JBrowse link
G Cyp2e1 cytochrome P450, family 2, subfamily e, polypeptide 1 multiple interactions EXP
ISO		 Dicumarol promotes the reaction [CYP2E1 protein results in increased reduction of tirapazamine]
Dicumarol inhibits the reaction [[CYP2E1 protein co-treated with Paraquat] results in increased expression of KLF6 protein]; Dicumarol inhibits the reaction [[CYP2E1 protein co-treated with Vitamin K 3] results in increased expression of KLF6 protein]		 CTD PMID:7710944 PMID:22486562 NCBI chr 1:195,840,330...195,850,728
Ensembl chr 1:195,840,058...195,864,023 		JBrowse link
G Drd5 dopamine receptor D5 increases expression EXP Dicumarol results in increased expression of DRD5 mRNA CTD PMID:18522901 NCBI chr14:72,487,950...72,491,050
Ensembl chr14:72,489,347...72,490,774 		JBrowse link
G Fabp1 fatty acid binding protein 1 multiple interactions EXP Dicoumarol inhibits the reaction [3-(p-azidobenzyl)-4-hydroxycoumarin binds to Fabp1 protein] RGD PMID:1939124 RGD:1626448 NCBI chr 4:103,191,015...103,194,791
Ensembl chr 4:103,191,006...103,194,788 		JBrowse link
G Gpr35 G protein-coupled receptor 35 multiple interactions ISO
EXP		 Dicumarol binds to and results in increased activity of GPR35 protein CTD PMID:20919992 NCBI chr 9:93,527,165...93,539,573
Ensembl chr 9:93,527,127...93,539,299 		JBrowse link
G Hspa5 heat shock protein family A (Hsp70) member 5 multiple interactions ISO Dicumarol inhibits the reaction [1-nitropyrene results in increased expression of HSPA5 protein] CTD PMID:19460413 NCBI chr 3:18,055,507...18,059,969
Ensembl chr 3:18,055,405...18,059,891 		JBrowse link
G Igf1 insulin-like growth factor 1 multiple interactions ISO Dicumarol inhibits the reaction [IGF1 protein results in increased phosphorylation of JUN protein] CTD PMID:11278392 NCBI chr 7:22,282,895...22,361,972
Ensembl chr 7:22,282,930...22,359,296 		JBrowse link
G Il1b interleukin 1 beta multiple interactions ISO Dicumarol inhibits the reaction [IL1B protein results in increased expression of TP53 protein] CTD PMID:17959154 NCBI chr 3:116,577,005...116,583,386
Ensembl chr 3:116,577,010...116,583,415 		JBrowse link
G Jun Jun proto-oncogene, AP-1 transcription factor subunit multiple interactions ISO Dicumarol inhibits the reaction [IGF1 protein results in increased phosphorylation of JUN protein]; Dicumarol inhibits the reaction [TNF protein results in increased phosphorylation of JUN protein] CTD PMID:11278392 PMID:17669387 NCBI chr 5:109,894,175...109,897,268
Ensembl chr 5:109,893,145...109,897,656 		JBrowse link
G Klf6 KLF transcription factor 6 multiple interactions ISO Dicumarol inhibits the reaction [[CYP2E1 protein co-treated with Paraquat] results in increased expression of KLF6 protein]; Dicumarol inhibits the reaction [[CYP2E1 protein co-treated with Vitamin K 3] results in increased expression of KLF6 protein] CTD PMID:22486562 NCBI chr17:64,539,456...64,548,451
Ensembl chr17:64,531,463...64,588,570 		JBrowse link
G Mapk1 mitogen activated protein kinase 1 multiple interactions ISO Dicumarol inhibits the reaction [TNF protein results in increased phosphorylation of MAPK1 protein] CTD PMID:17669387 NCBI chr11:83,957,813...84,023,629
Ensembl chr11:83,957,813...84,023,616 		JBrowse link
G Mapk10 mitogen activated protein kinase 10 multiple interactions
decreases activity		 ISO Dicumarol inhibits the reaction [Anisomycin results in increased activity of MAPK10 protein]; Dicumarol inhibits the reaction [Sorbitol results in increased activity of MAPK10 protein]; Dicumarol inhibits the reaction [TRAF2 protein results in increased activity of MAPK10 protein]; NQO1 protein inhibits the reaction [Dicumarol results in decreased activity of MAPK10 protein] CTD PMID:10531305 NCBI chr14:6,497,662...6,790,109
Ensembl chr14:6,497,707...6,786,201 		JBrowse link
G Mapk3 mitogen activated protein kinase 3 multiple interactions ISO Dicumarol inhibits the reaction [TNF protein results in increased phosphorylation of MAPK3 protein] CTD PMID:17669387 NCBI chr 1:181,366,646...181,372,863
Ensembl chr 1:181,366,637...181,372,863 		JBrowse link
G Mapk8 mitogen-activated protein kinase 8 multiple interactions ISO Dicumarol inhibits the reaction [Adenosine Diphosphate results in increased phosphorylation of MAPK8 protein]; Dicumarol inhibits the reaction [Arsenic Trioxide results in increased activity of MAPK8 protein] CTD PMID:14701702 PMID:24466103 NCBI chr16:8,638,897...8,721,960
Ensembl chr16:8,638,924...8,721,981 		JBrowse link
G Mapk9 mitogen-activated protein kinase 9 multiple interactions ISO Dicumarol inhibits the reaction [Adenosine Diphosphate results in increased phosphorylation of MAPK9 protein] CTD PMID:24466103 NCBI chr10:34,169,661...34,211,138
Ensembl chr10:34,169,675...34,210,178 		JBrowse link
G Mmp9 matrix metallopeptidase 9 multiple interactions ISO Dicumarol inhibits the reaction [TNF protein results in increased expression of and results in increased secretion of MMP9 protein]; Dicumarol inhibits the reaction [TNF protein results in increased expression of MMP9 mRNA]; hydroquinone inhibits the reaction [Dicumarol inhibits the reaction [TNF protein results in increased expression of and results in increased secretion of MMP9 protein]] CTD PMID:17669387 NCBI chr 3:153,684,158...153,692,118
Ensembl chr 3:153,683,858...153,692,120 		JBrowse link
G Mt1 metallothionein 1 multiple interactions ISO Dicumarol inhibits the reaction [Cadmium Chloride results in increased expression of MT1 mRNA]; Dicumarol inhibits the reaction [zinc chloride results in increased expression of MT1 mRNA]; Dicumarol inhibits the reaction [Zinc Sulfate results in increased expression of MT1 mRNA] CTD PMID:11551972 PMID:15142038 NCBI chr19:10,826,032...10,827,048
Ensembl chr19:10,826,032...10,827,049
Ensembl chr17:10,826,032...10,827,049 		JBrowse link
G Nfkb1 nuclear factor kappa B subunit 1 multiple interactions ISO Dicumarol inhibits the reaction [Lipopolysaccharides results in increased activity of NFKB1 protein]; Dicumarol inhibits the reaction [TNF protein results in increased activity of NFKB1 protein] CTD PMID:10531305 NCBI chr 2:224,016,214...224,132,135
Ensembl chr 2:224,016,214...224,110,404 		JBrowse link
G Nqo1 NAD(P)H quinone dehydrogenase 1 multiple interactions
affects response to substance
decreases activity
decreases expression		 ISO
EXP		 [aristolochic acid I co-treated with Dicumarol] results in increased expression of NQO1 protein; [Dicumarol results in decreased activity of NQO1 protein] inhibits the reaction [Eugenol results in increased expression of CD86 protein]; [Dicumarol results in decreased activity of NQO1 protein] which results in decreased susceptibility to Mitomycin; [Dicumarol results in decreased activity of NQO1 protein] which results in decreased susceptibility to Streptonigrin; aristolochic acid I inhibits the reaction [Dicumarol results in decreased activity of NQO1 protein]; Dicumarol inhibits the reaction [[arsenite results in increased expression of NQO1 protein] which results in increased susceptibility to Mitomycin]; Dicumarol inhibits the reaction [NQO1 protein results in decreased susceptibility to arsenite]; Dicumarol inhibits the reaction [NQO1 protein results in increased metabolism of Mitomycin]; Dicumarol inhibits the reaction [NQO1 protein results in increased reduction of 2,6-Dichloroindophenol]; Dicumarol inhibits the reaction [TP53 protein binds to NQO1 protein]; NQO1 protein inhibits the reaction [Dicumarol results in decreased activity of MAPK10 protein]
NQO1 protein affects the susceptibility to Dicumarol
[Dicumarol results in decreased activity of NQO1 protein] which results in decreased abundance of aristolactam I; [Dicumarol results in decreased activity of NQO1 protein] which results in increased abundance of aristolochic acid I; [Dicumarol results in decreased activity of NQO1 protein] which results in increased abundance of aristolochic acid I metabolite
[Dicumarol results in decreased activity of NQO1 protein] which results in decreased reduction of Chromium; Dicumarol inhibits the reaction [Benzo(a)pyrene results in increased activity of NQO1 protein]; Dicumarol inhibits the reaction [NQO1 protein inhibits the reaction [Vitamin K 3 results in increased chemical synthesis of Hydrogen Peroxide]]; Dicumarol inhibits the reaction [Progesterone results in increased activity of NQO1 protein]; Dicumarol inhibits the reaction [Tetrachlorodibenzodioxin results in increased activity of NQO1 protein]
Dicumarol results in decreased expression of NQO1 protein
[Dicumarol results in decreased activity of NQO1 protein] which results in decreased activity of diaziquone; Dicumarol results in decreased activity of NQO1 protein		 CTD PMID:1379126 PMID:1701346 PMID:2113030 PMID:8572925 PMID:10092053 More... NCBI chr19:35,295,633...35,310,528
Ensembl chr19:35,295,573...35,310,557 		JBrowse link
G Rb1 RB transcriptional corepressor 1 increases phosphorylation ISO Dicumarol results in increased phosphorylation of RB1 protein CTD PMID:15896341 NCBI chr15:48,371,295...48,502,473
Ensembl chr15:48,371,296...48,502,302 		JBrowse link
G Rb1cc1 RB1-inducible coiled-coil 1 multiple interactions ISO Dicumarol inhibits the reaction [RB1CC1 protein results in increased expression of CDKN1A protein]; Dicumarol inhibits the reaction [RB1CC1 protein results in increased expression of TP53 protein]; Dicumarol inhibits the reaction [RB1CC1 protein results in increased stability of TP53 protein] CTD PMID:16061648 NCBI chr 5:13,161,648...13,225,560
Ensembl chr 5:13,161,648...13,225,560 		JBrowse link
G Rela RELA proto-oncogene, NF-kB subunit multiple interactions ISO Dicumarol inhibits the reaction [Lipopolysaccharides results in increased activity of RELA protein]; Dicumarol inhibits the reaction [TNF protein affects the localization of RELA protein]; Dicumarol inhibits the reaction [TNF protein results in increased activity of RELA protein] CTD PMID:10531305 PMID:17669387 NCBI chr 1:202,925,001...202,935,484
Ensembl chr 1:202,924,945...202,935,484 		JBrowse link
G Slc30a1 solute carrier family 30 member 1 multiple interactions ISO Dicumarol inhibits the reaction [Cadmium Chloride results in increased expression of SLC30A1 mRNA]; Dicumarol inhibits the reaction [Zinc Sulfate results in increased expression of SLC30A1 mRNA] CTD PMID:15142038 NCBI chr13:103,491,037...103,494,910
Ensembl chr13:103,491,037...103,494,910 		JBrowse link
G Sod1 superoxide dismutase 1 multiple interactions EXP [Dopamine co-treated with Dicumarol co-treated with Copper Sulfate] results in decreased expression of SOD1 mRNA CTD PMID:11299314 NCBI chr11:29,456,673...29,462,249
Ensembl chr11:29,456,558...29,462,249 		JBrowse link
G Sod2 superoxide dismutase 2 decreases response to substance
multiple interactions		 ISO
EXP		 SOD2 protein results in decreased susceptibility to Dicumarol
[Dopamine co-treated with Dicumarol co-treated with Copper Sulfate] results in decreased expression of SOD2 mRNA		 CTD PMID:11299314 PMID:17040906 NCBI chr 1:47,638,318...47,645,163
Ensembl chr 1:47,636,528...47,645,189 		JBrowse link
G Tnf tumor necrosis factor multiple interactions ISO Dicumarol inhibits the reaction [TNF protein affects the localization of RELA protein]; Dicumarol inhibits the reaction [TNF protein results in increased activity of NFKB1 protein]; Dicumarol inhibits the reaction [TNF protein results in increased activity of RELA protein]; Dicumarol inhibits the reaction [TNF protein results in increased expression of and results in increased secretion of MMP9 protein]; Dicumarol inhibits the reaction [TNF protein results in increased expression of MMP9 mRNA]; Dicumarol inhibits the reaction [TNF protein results in increased phosphorylation of JUN protein]; Dicumarol inhibits the reaction [TNF protein results in increased phosphorylation of MAPK1 protein]; Dicumarol inhibits the reaction [TNF protein results in increased phosphorylation of MAPK3 protein]; hydroquinone inhibits the reaction [Dicumarol inhibits the reaction [TNF protein results in increased expression of and results in increased secretion of MMP9 protein]] CTD PMID:10531305 PMID:17669387 NCBI chr20:3,622,011...3,624,629
Ensembl chr20:3,622,011...3,624,629 		JBrowse link
G Tp53 tumor protein p53 multiple interactions
increases degradation
decreases expression		 ISO Dicumarol inhibits the reaction [2,5-diaziridinyl-3-(hydroxymethyl)-6-methyl-1,4-benzoquinone analog results in increased expression of TP53 protein modified form]; Dicumarol inhibits the reaction [2,5-diaziridinyl-3-(hydroxymethyl)-6-methyl-1,4-benzoquinone analog results in increased expression of TP53 protein]; Dicumarol inhibits the reaction [IL1B protein results in increased expression of TP53 protein]; Dicumarol inhibits the reaction [RB1CC1 protein results in increased expression of TP53 protein]; Dicumarol inhibits the reaction [RB1CC1 protein results in increased stability of TP53 protein]; Dicumarol inhibits the reaction [TP53 protein binds to NQO1 protein]
Dicumarol results in increased degradation of TP53 protein
Dicumarol results in decreased expression of TP53 protein		 CTD PMID:14634213 PMID:16061648 PMID:17959154 PMID:22692362 PMID:26630137 NCBI chr10:54,300,070...54,311,525
Ensembl chr10:54,300,048...54,311,524 		JBrowse link
G Traf2 Tnf receptor-associated factor 2 multiple interactions ISO Dicumarol inhibits the reaction [TRAF2 protein results in increased activity of MAPK10 protein] CTD PMID:10531305 NCBI chr 3:8,341,950...8,366,609
Ensembl chr 3:8,341,951...8,366,538 		JBrowse link
G Vkorc1 vitamin K epoxide reductase complex, subunit 1 decreases activity
multiple interactions		 ISO Dicumarol results in decreased activity of VKORC1 protein
Dicumarol inhibits the reaction [VKORC1 protein results in increased reduction of Vitamin K 1]		 CTD PMID:29581108 NCBI chr 1:182,502,491...182,505,012
Ensembl chr 1:182,500,844...182,505,008 		JBrowse link
G Vkorc1l1 vitamin K epoxide reductase complex, subunit 1-like 1 multiple interactions
decreases activity		 ISO Dicumarol inhibits the reaction [VKORC1L1 protein results in increased reduction of Vitamin K 1]
Dicumarol results in decreased activity of VKORC1L1 protein		 CTD PMID:29581108 NCBI chr12:26,717,959...26,768,193
Ensembl chr12:26,623,976...26,768,225 		JBrowse link
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  CHEBI ontology 19848
    role 19824
      biological role 19822
        pharmacological role 19064
          antagonist 17248
            vitamin K antagonist 221
              dicoumarol 38
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  CHEBI ontology 19848
    subatomic particle 19846
      composite particle 19846
        hadron 19846
          baryon 19846
            nucleon 19846
              atomic nucleus 19846
                atom 19846
                  main group element atom 19796
                    p-block element atom 19796
                      carbon group element atom 19741
                        carbon atom 19737
                          organic molecular entity 19737
                            organic molecule 19690
                              organic cyclic compound 19501
                                organic heterocyclic compound 18878
                                  oxacycle 17891
                                    benzopyran 11959
                                      1-benzopyran 11713
                                        chromenes 4429
                                          chromenone 4373
                                            coumarins 4145
                                              hydroxycoumarin 355
                                                dicoumarol 38
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