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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 chr17:69,441,253...69,460,334
Ensembl chr17:69,441,223...69,460,321
JBrowse link
G Alb albumin affects binding ISO Dicumarol binds to ALB protein CTD PMID:62049 NCBI chr14:19,176,275...19,191,793
Ensembl chr14:19,176,277...19,191,863
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 8:58,015,938...58,119,973
Ensembl chr 8:58,015,940...58,120,045
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 chr16:48,845,011...48,863,249
Ensembl chr16:48,845,012...48,863,204
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 3:93,379,872...93,412,058
Ensembl chr 3:93,379,874...93,412,058
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 chr11:67,060,305...67,117,990
Ensembl chr11:67,082,193...67,118,795
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 [RB1CC1 protein results in increased expression of CDKN1A protein] CTD PMID:9343371, PMID:16061648 NCBI chr20:6,348,422...6,358,864
Ensembl chr20:6,351,458...6,358,864
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 4:80,331,226...80,333,326
Ensembl chr 4:80,331,227...80,333,326
JBrowse link
G Cyp2e1 cytochrome P450, family 2, subfamily e, polypeptide 1 multiple interactions EXP Dicumarol promotes the reaction [CYP2E1 protein results in increased reduction of tirapazamine] CTD PMID:7710944 NCBI chr 1:213,511,892...213,522,195
Ensembl chr 1:213,511,874...213,535,542
JBrowse link
G Drd5 dopamine receptor D5 increases expression EXP Dicumarol results in increased expression of DRD5 mRNA CTD PMID:18522901 NCBI chr14:77,220,579...77,222,006
Ensembl chr14:77,220,579...77,222,006
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 3:13,838,304...13,842,763
Ensembl chr 3:13,838,304...13,842,762
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 7:28,412,123...28,491,815
Ensembl chr 7:28,412,198...28,486,609
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 3:121,876,256...121,882,637
Ensembl chr 3:121,876,263...121,882,726
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 5:114,011,184...114,014,277
Ensembl chr 5:114,011,189...114,014,277
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 chr11:88,203,863...88,273,301
Ensembl chr11:88,211,599...88,273,254
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 chr14:8,079,955...8,371,508
Ensembl chr14:8,080,275...8,368,254
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 1:198,192,773...198,198,975
Ensembl chr 1:198,192,773...198,198,975
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 chr16:9,620,854...9,709,342
Ensembl chr16:9,625,177...9,709,347
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 chr10:35,333,859...35,374,364
Ensembl chr10:35,333,859...35,374,355
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 3:161,413,410...161,421,473
Ensembl chr 3:161,413,298...161,421,520
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 chr19:11,301,991...11,303,007
Ensembl chr17:78,793,336...78,793,724
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 2:240,773,520...240,890,053
Ensembl chr 2:240,773,456...240,866,689
JBrowse link
G Nqo1 NAD(P)H quinone dehydrogenase 1 multiple interactions
decreases activity
decreases expression
affects response to substance
ISO
EXP
[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; 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]
[Dicumarol results in decreased activity of NQO1 protein] which results in decreased activity of diaziquone; Dicumarol results in decreased activity of NQO1 protein
Dicumarol results in decreased expression of NQO1 protein
[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 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
NQO1 protein affects the susceptibility to Dicumarol
CTD PMID:1379126, PMID:1701346, PMID:2113030, PMID:8572925, PMID:10092053, PMID:10531305, PMID:11154737, PMID:14634213, PMID:15655414, PMID:15805261, PMID:16494910, PMID:17669387, PMID:17979524, PMID:19497421, PMID:21613233, PMID:21742781, PMID:21947872, PMID:27558805, PMID:29281794 NCBI chr19:38,422,210...38,437,103
Ensembl chr19:38,422,164...38,437,180
JBrowse link
G Rb1 RB transcriptional corepressor 1 increases phosphorylation ISO Dicumarol results in increased phosphorylation of RB1 protein CTD PMID:15896341 NCBI chr15:55,081,582...55,209,060
Ensembl chr15:55,083,140...55,209,342
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 5:13,033,918...13,097,369
Ensembl chr 5:13,033,918...13,097,341
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 1:220,992,770...221,003,249
Ensembl chr 1:220,992,770...221,003,249
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 chr13:110,677,810...110,681,683
Ensembl chr13:110,677,810...110,681,683
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 chr11:30,363,282...30,368,858
Ensembl chr11:30,363,280...30,368,862
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 1:47,914,757...47,921,587
Ensembl chr 1:47,914,759...47,921,587
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 chr20:5,189,382...5,192,000
Ensembl chr20:5,189,390...5,192,000
JBrowse link
G Tp53 tumor protein p53 multiple interactions
decreases expression
increases degradation
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 decreased expression of TP53 protein
Dicumarol results in increased degradation of TP53 protein
CTD PMID:14634213, PMID:16061648, PMID:17959154, PMID:22692362, PMID:26630137 NCBI chr10:56,186,299...56,198,449
Ensembl chr10:56,187,020...56,198,449
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 3:2,746,061...2,770,690
Ensembl chr 3:2,746,075...2,770,620
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 1:199,338,785...199,341,306
Ensembl chr 1:199,337,138...199,341,302
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 chr12:30,218,825...30,268,990
Ensembl chr12:30,222,701...30,268,990
JBrowse link

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  CHEBI ontology 19816
    role 19764
      biological role 19764
        pharmacological role 18825
          antagonist 16213
            vitamin K antagonist 201
              dicoumarol 34
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  CHEBI ontology 19816
    subatomic particle 19814
      composite particle 19814
        hadron 19814
          baryon 19814
            nucleon 19814
              atomic nucleus 19814
                atom 19814
                  main group element atom 19702
                    p-block element atom 19702
                      carbon group element atom 19608
                        carbon atom 19597
                          organic molecular entity 19597
                            organic molecule 19522
                              organic cyclic compound 19320
                                organic heterocyclic compound 18432
                                  oxacycle 17200
                                    benzopyran 10142
                                      1-benzopyran 9858
                                        chromenes 932
                                          chromenone 853
                                            coumarins 574
                                              hydroxycoumarin 301
                                                dicoumarol 34
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RGD is funded by grant HL64541 from the National Heart, Lung, and Blood Institute on behalf of the NIH.