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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:tadalafil
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Accession:CHEBI:71940 term browser browse the term
Definition:A pyrazinopyridoindole that is 2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione substituted at position 2 by a methyl group and at position 6 by a 1,3-benzodioxol-5-yl group (the 6R,12aR-diastereomer). A phosphodiesterase V inhibitor inhibitor, currently marketed in pill form for treating erectile dysfunction under the name Cialis; and under the name Adcirca for the treatment of pulmonary arterial hypertension.
Synonyms:exact_synonym: (6R,12aR)-6-(1,3-benzodioxol-5-yl)-2-methyl-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione
 related_synonym: (6R,12aR)-2,3,6,7,12,12a-Hexahydro-2-methyl-6-(3,4-(methylenedioxy)phenyl) pyrazino(1',2':1,6)pyrido(3,4-b)indole-1,4-dione;   (6R-trans)-6-(1,3-Benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydro-2-methyl-pyrazino(1',2':1,6)pyrido(3,4-b)indole-1,4-dione;   6-BENZO[1,3]DIOXOL-5-YL-2-METHYL-2,3,6,7,12,12A-HEXAHYDRO-PYRAZINO[1',2':1,6]PYRIDO[3,4-B]INDOLE-1,4-DIONE;   Adcirca;   Cialis;   Formula=C22H19N3O4;   InChI=1S/C22H19N3O4/c1-24-10-19(26)25-16(22(24)27)9-14-13-4-2-3-5-15(13)23-20(14)21(25)12-6-7-17-18(8-12)29-11-28-17/h2-8,16,21,23H,9-11H2,1H3/t16-,21-/m1/s1;   InChIKey=WOXKDUGGOYFFRN-IIBYNOLFSA-N;   SMILES=[H][C@]12Cc3c([nH]c4ccccc34)[C@H](N1C(=O)CN(C)C2=O)c1ccc2OCOc2c1
 alt_id: CHEBI:32177;   CHEBI:41488
 xref: CAS:171596-29-5;   DrugBank:DB00820;   Drug_Central:2553;   HMDB:HMDB0014958;   KEGG:D02008;   LINCS:LSM-4109
 xref_mesh: MESH:D000068581
 xref: PDBeChem:CIA;   PMID:21056623;   PMID:21680058;   PMID:22014651;   PMID:22328305;   PMID:22494518;   PMID:22776546;   PMID:22816778;   PMID:22971615;   PMID:22982422;   PMID:22996758;   PMID:23033484;   PMID:23072271;   PMID:23118430;   PMID:23140258;   PMID:23190275;   PMID:23216015;   PMID:23219525;   PMID:23234619;   PMID:23312193;   PMID:23346990;   PMID:23347176;   Patent:EP2107059;   Patent:EP2238979;   Patent:US2003229080;   Patent:US2004157847;   Patent:WO2005068464;   Patent:WO2007113243;   Patent:WO2009144734;   Patent:WO2010049500;   Patent:WO2012107549;   Reaxys:9589181;   Wikipedia:Tadalafil


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tadalafil term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Abcg2 ATP binding cassette subfamily G member 2 multiple interactions EXP Tadalafil inhibits the reaction [[Aflatoxin B1 co-treated with Ethanol] results in increased expression of ABCG2 mRNA] CTD PMID:35608386 NCBI chr 4:87,676,241...87,802,757
Ensembl chr 4:87,745,319...87,802,409 		JBrowse link
G Adipoq adiponectin, C1Q and collagen domain containing multiple interactions EXP Tadalafil inhibits the reaction [Epinephrine results in decreased expression of ADIPOQ protein] CTD PMID:29233027 NCBI chr11:77,721,912...77,735,644
Ensembl chr11:77,721,912...77,735,564 		JBrowse link
G Aif1 allograft inflammatory factor 1 multiple interactions ISO Tadalafil inhibits the reaction [Thioacetamide results in increased expression of AIF1 protein] CTD PMID:31323263 NCBI chr20:3,646,784...3,652,670
Ensembl chr20:3,646,777...3,652,668 		JBrowse link
G Akt1 AKT serine/threonine kinase 1 multiple interactions EXP Tadalafil inhibits the reaction [[Aflatoxin B1 co-treated with Ethanol] results in increased expression of AKT1 mRNA] CTD PMID:35608386 NCBI chr 6:131,713,716...131,735,319
Ensembl chr 6:131,713,720...131,733,921 		JBrowse link
G App amyloid beta precursor protein multiple interactions ISO Tadalafil inhibits the reaction [Streptozocin results in increased expression of APP protein modified form] CTD PMID:34428446 NCBI chr11:24,019,774...24,236,584
Ensembl chr11:24,019,778...24,236,561 		JBrowse link
G Bax BCL2 associated X, apoptosis regulator multiple interactions EXP Sildenafil Citrate promotes the reaction [Tadalafil inhibits the reaction [Streptozocin results in increased expression of BAX mRNA]]; Tadalafil inhibits the reaction [Cisplatin results in increased expression of BAX mRNA]; Tadalafil inhibits the reaction [Streptozocin results in increased expression of BAX mRNA]; Tadalafil promotes the reaction [Sildenafil Citrate inhibits the reaction [Streptozocin results in increased expression of BAX mRNA]]; Testosterone promotes the reaction [Sildenafil Citrate promotes the reaction [Tadalafil inhibits the reaction [Streptozocin results in increased expression of BAX mRNA]]]; Testosterone promotes the reaction [Tadalafil inhibits the reaction [Streptozocin results in increased expression of BAX mRNA]]; Testosterone promotes the reaction [Tadalafil promotes the reaction [Sildenafil Citrate inhibits the reaction [Streptozocin results in increased expression of BAX mRNA]]]; zinc protoporphyrin inhibits the reaction [Tadalafil inhibits the reaction [Cisplatin results in increased expression of BAX mRNA]] CTD PMID:20574430 PMID:32621855 NCBI chr 1:95,940,001...95,945,407
Ensembl chr 1:95,938,808...95,945,368 		JBrowse link
G Bcl2 BCL2, apoptosis regulator multiple interactions ISO
EXP		 Tadalafil inhibits the reaction [Doxorubicin results in decreased expression of BCL2 protein]
Sildenafil Citrate promotes the reaction [Tadalafil inhibits the reaction [Streptozocin results in decreased expression of BCL2 mRNA]]; Tadalafil inhibits the reaction [Cisplatin results in decreased expression of BCL2 protein]; Tadalafil inhibits the reaction [Streptozocin results in decreased expression of BCL2 mRNA]; Tadalafil promotes the reaction [Sildenafil Citrate inhibits the reaction [Streptozocin results in decreased expression of BCL2 mRNA]]; Testosterone promotes the reaction [Sildenafil Citrate promotes the reaction [Tadalafil inhibits the reaction [Streptozocin results in decreased expression of BCL2 mRNA]]]; Testosterone promotes the reaction [Tadalafil inhibits the reaction [Streptozocin results in decreased expression of BCL2 mRNA]]; Testosterone promotes the reaction [Tadalafil promotes the reaction [Sildenafil Citrate inhibits the reaction [Streptozocin results in decreased expression of BCL2 mRNA]]]; zinc protoporphyrin inhibits the reaction [Tadalafil inhibits the reaction [Cisplatin results in decreased expression of BCL2 protein]]		 CTD PMID:20543097 PMID:20574430 PMID:32621855 NCBI chr13:22,689,783...22,853,920
Ensembl chr13:22,684,989...22,853,743
Ensembl chr13:22,684,989...22,853,743 		JBrowse link
G Bdnf brain-derived neurotrophic factor multiple interactions ISO Tadalafil inhibits the reaction [Streptozocin results in decreased expression of BDNF protein]; Tadalafil inhibits the reaction [Thioacetamide results in decreased expression of BDNF protein] CTD PMID:31323263 PMID:34428446 NCBI chr 3:96,165,042...96,215,621
Ensembl chr 3:96,165,042...96,215,615 		JBrowse link
G Becn1 beclin 1 multiple interactions ISO Tadalafil inhibits the reaction [Streptozocin results in decreased expression of BECN1 protein modified form] CTD PMID:34428446 NCBI chr10:86,231,387...86,246,742
Ensembl chr10:86,231,388...86,246,742 		JBrowse link
G Bmp2 bone morphogenetic protein 2 decreases expression ISO Tadalafil results in decreased expression of BMP2 mRNA CTD PMID:32513693 NCBI chr 3:120,812,660...120,822,579
Ensembl chr 3:120,812,882...120,821,397 		JBrowse link
G Casp3 caspase 3 multiple interactions EXP Tadalafil inhibits the reaction [Cisplatin results in increased expression of CASP3 mRNA]; Tadalafil inhibits the reaction [Epinephrine results in increased expression of CASP3 protein]; zinc protoporphyrin inhibits the reaction [Tadalafil inhibits the reaction [Cisplatin results in increased expression of CASP3 mRNA]] CTD PMID:29233027 PMID:32621855 NCBI chr16:45,662,910...45,681,171
Ensembl chr16:45,662,910...45,684,648 		JBrowse link
G Cat catalase multiple interactions EXP Tadalafil inhibits the reaction [Cisplatin results in decreased expression of CAT protein]; zinc protoporphyrin inhibits the reaction [Tadalafil inhibits the reaction [Cisplatin results in decreased expression of CAT protein]] CTD PMID:32621855 NCBI chr 3:89,842,393...89,874,577
Ensembl chr 3:89,842,399...89,874,478 		JBrowse link
G Ccnd1 cyclin D1 multiple interactions ISO Tadalafil inhibits the reaction [Streptozocin results in decreased expression of CCND1 mRNA] CTD PMID:34428446 NCBI chr 1:200,089,002...200,098,524
Ensembl chr 1:200,089,002...200,098,602 		JBrowse link
G Creb1 cAMP responsive element binding protein 1 multiple interactions ISO Tadalafil inhibits the reaction [Thioacetamide results in decreased phosphorylation of CREB1 protein] CTD PMID:31323263 NCBI chr 9:65,903,511...65,972,562
Ensembl chr 9:65,903,547...65,970,816 		JBrowse link
G Ctnnb1 catenin beta 1 multiple interactions ISO Tadalafil inhibits the reaction [Streptozocin results in increased phosphorylation of CTNNB1 protein] CTD PMID:34428446 NCBI chr 8:120,640,008...120,667,110
Ensembl chr 8:120,639,995...120,667,111 		JBrowse link
G G6pd glucose-6-phosphate dehydrogenase increases activity EXP Tadalafil results in increased activity of G6PD protein CTD PMID:24911673 NCBI chr  X:152,201,081...152,220,863
Ensembl chr  X:152,201,098...152,220,801 		JBrowse link
G Gata4 GATA binding protein 4 multiple interactions ISO Tadalafil inhibits the reaction [Doxorubicin results in decreased expression of GATA4 protein] CTD PMID:20543097 NCBI chr15:37,459,601...37,531,291
Ensembl chr15:37,459,601...37,505,636 		JBrowse link
G Gcg glucagon decreases activity EXP Tadalafil results in decreased activity of GCG protein CTD PMID:24911673 NCBI chr 3:47,113,914...47,122,958
Ensembl chr 3:47,113,914...47,122,929 		JBrowse link
G Gfap glial fibrillary acidic protein multiple interactions ISO Tadalafil inhibits the reaction [Thioacetamide results in increased expression of GFAP protein] CTD PMID:31323263 NCBI chr10:87,852,891...87,861,631
Ensembl chr10:87,852,890...87,861,589 		JBrowse link
G Got1 glutamic-oxaloacetic transaminase 1 multiple interactions EXP Tadalafil inhibits the reaction [Aflatoxin B1 results in increased activity of GOT1 protein] CTD PMID:35608386 NCBI chr 1:242,357,293...242,381,535
Ensembl chr 1:242,357,306...242,380,633 		JBrowse link
G Gpt glutamic--pyruvic transaminase multiple interactions EXP Tadalafil inhibits the reaction [Aflatoxin B1 results in increased activity of GPT protein] CTD PMID:35608386 NCBI chr 7:108,416,646...108,419,495
Ensembl chr 7:108,416,642...108,419,494 		JBrowse link
G Gria1 glutamate ionotropic receptor AMPA type subunit 1 multiple interactions ISO Tadalafil inhibits the reaction [Thioacetamide results in decreased expression of GRIA1 protein] CTD PMID:31323263 NCBI chr10:41,210,713...41,527,283
Ensembl chr10:41,210,713...41,527,283 		JBrowse link
G Gria2 glutamate ionotropic receptor AMPA type subunit 2 multiple interactions ISO Tadalafil inhibits the reaction [Thioacetamide results in decreased expression of GRIA2 protein] CTD PMID:31323263 NCBI chr 2:165,949,379...166,069,510
Ensembl chr 2:165,947,521...166,069,510 		JBrowse link
G Grin2a glutamate ionotropic receptor NMDA type subunit 2A multiple interactions ISO Tadalafil inhibits the reaction [Thioacetamide results in decreased expression of GRIN2A protein] CTD PMID:31323263 NCBI chr10:5,629,683...6,053,262
Ensembl chr10:5,631,369...6,044,637 		JBrowse link
G Gsk3b glycogen synthase kinase 3 beta multiple interactions ISO Tadalafil inhibits the reaction [Streptozocin results in decreased phosphorylation of GSK3B protein]; Tadalafil inhibits the reaction [Thioacetamide results in decreased phosphorylation of GSK3B protein] CTD PMID:31323263 PMID:34428446 NCBI chr11:62,498,997...62,648,665
Ensembl chr11:62,504,316...62,648,646 		JBrowse link
G Hif1a hypoxia inducible factor 1 subunit alpha multiple interactions EXP Tadalafil inhibits the reaction [[Aflatoxin B1 co-treated with Ethanol] results in increased expression of HIF1A protein] CTD PMID:35608386 NCBI chr 6:92,624,059...92,669,262
Ensembl chr 6:92,624,390...92,669,261 		JBrowse link
G Hmox1 heme oxygenase 1 multiple interactions EXP Tadalafil promotes the reaction [Cisplatin results in increased expression of HMOX1 mRNA]; Tadalafil promotes the reaction [Cisplatin results in increased expression of HMOX1 protein]; zinc protoporphyrin inhibits the reaction [Tadalafil promotes the reaction [Cisplatin results in increased expression of HMOX1 protein]] CTD PMID:32621855 NCBI chr19:13,466,287...13,474,082
Ensembl chr19:13,467,244...13,474,079 		JBrowse link
G Il1b interleukin 1 beta multiple interactions
decreases expression		 EXP
ISO		 Tadalafil inhibits the reaction [Oxygen deficiency results in increased expression of IL1B mRNA]
Tadalafil results in decreased expression of IL1B mRNA
Tadalafil inhibits the reaction [Thioacetamide results in increased expression of IL1B protein]		 CTD PMID:16368379 PMID:31323263 NCBI chr 3:116,577,005...116,583,386
Ensembl chr 3:116,577,010...116,583,415 		JBrowse link
G Il23a interleukin 23 subunit alpha multiple interactions ISO Tadalafil inhibits the reaction [Streptozocin results in increased expression of IL23A protein] CTD PMID:34428446 NCBI chr 7:721,809...723,923
Ensembl chr 7:721,809...723,923 		JBrowse link
G Il27 interleukin 27 multiple interactions ISO Tadalafil inhibits the reaction [Streptozocin results in increased expression of IL27 protein] CTD PMID:34428446 NCBI chr 1:181,173,108...181,178,720
Ensembl chr 1:181,173,372...181,178,582 		JBrowse link
G Il6 interleukin 6 multiple interactions ISO Tadalafil inhibits the reaction [Thioacetamide results in increased expression of IL6 protein] CTD PMID:31323263 NCBI chr 4:5,214,602...5,219,178
Ensembl chr 4:5,213,394...5,219,178 		JBrowse link
G Ldha lactate dehydrogenase A multiple interactions EXP Tadalafil inhibits the reaction [[Aflatoxin B1 co-treated with Ethanol] results in increased expression of LDHA mRNA] CTD PMID:35608386 NCBI chr 1:97,371,823...97,381,247
Ensembl chr 1:97,366,021...97,433,472 		JBrowse link
G Mapk1 mitogen activated protein kinase 1 increases phosphorylation
multiple interactions		 ISO Tadalafil results in increased phosphorylation of MAPK1 protein
Tadalafil inhibits the reaction [Thioacetamide results in increased phosphorylation of MAPK1 protein]		 CTD PMID:18082193 PMID:31323263 NCBI chr11:83,957,813...84,023,629
Ensembl chr11:83,957,813...84,023,616 		JBrowse link
G Mapk3 mitogen activated protein kinase 3 increases phosphorylation
multiple interactions		 ISO Tadalafil results in increased phosphorylation of MAPK3 protein
Tadalafil inhibits the reaction [Thioacetamide results in increased phosphorylation of MAPK3 protein]		 CTD PMID:18082193 PMID:31323263 NCBI chr 1:181,366,646...181,372,863
Ensembl chr 1:181,366,637...181,372,863 		JBrowse link
G Mapt microtubule-associated protein tau multiple interactions ISO Tadalafil inhibits the reaction [Streptozocin results in increased expression of MAPT protein modified form] CTD PMID:34428446 NCBI chr10:89,138,644...89,236,137
Ensembl chr10:89,138,627...89,236,129 		JBrowse link
G Mtor mechanistic target of rapamycin kinase multiple interactions ISO Tadalafil inhibits the reaction [Streptozocin results in increased expression of MTOR protein modified form] CTD PMID:34428446 NCBI chr 5:158,884,856...158,994,311
Ensembl chr 5:158,884,804...158,994,311 		JBrowse link
G Myc MYC proto-oncogene, bHLH transcription factor multiple interactions EXP Tadalafil inhibits the reaction [[Aflatoxin B1 co-treated with Ethanol] results in increased expression of MYC mRNA] CTD PMID:35608386 NCBI chr 7:93,593,705...93,598,633
Ensembl chr 7:93,593,705...93,598,630 		JBrowse link
G Nfe2l2 NFE2 like bZIP transcription factor 2 multiple interactions EXP Tadalafil promotes the reaction [Cisplatin results in increased expression of NFE2L2 mRNA] CTD PMID:32621855 NCBI chr 3:60,594,239...60,621,712
Ensembl chr 3:60,594,242...60,621,737 		JBrowse link
G Nos2 nitric oxide synthase 2 multiple interactions EXP Tadalafil inhibits the reaction [Cisplatin results in increased expression of NOS2 mRNA]; zinc protoporphyrin inhibits the reaction [Tadalafil inhibits the reaction [Cisplatin results in increased expression of NOS2 mRNA]] CTD PMID:32621855 NCBI chr10:63,815,308...63,851,208
Ensembl chr10:63,815,308...63,851,210 		JBrowse link
G Ogn osteoglycin increases expression ISO Tadalafil results in increased expression of OGN mRNA CTD PMID:32513693 NCBI chr17:15,032,069...15,052,626
Ensembl chr17:15,032,069...15,052,739 		JBrowse link
G Pde5a phosphodiesterase 5A decreases activity ISO Tadalafil results in decreased activity of PDE5A protein CTD PMID:15934858 PMID:16368379 PMID:17138653 NCBI chr 2:210,858,515...211,003,480
Ensembl chr 2:210,858,063...210,999,701 		JBrowse link
G Pfkfb3 6-phosphofructo-2-kinase/fructose-2,6-biphosphatase 3 multiple interactions EXP Tadalafil inhibits the reaction [[Ethanol co-treated with Aflatoxin B1] results in increased expression of PFKFB3 mRNA] CTD PMID:35608386 NCBI chr17:66,983,629...67,064,702
Ensembl chr17:66,983,686...67,063,125 		JBrowse link
G Ppp2ca protein phosphatase 2 catalytic subunit alpha multiple interactions ISO Tadalafil inhibits the reaction [Streptozocin results in decreased expression of PPP2CA protein modified form] CTD PMID:34428446 NCBI chr10:36,358,110...36,377,864
Ensembl chr10:36,358,101...36,377,862 		JBrowse link
G Prkg1 protein kinase cGMP-dependent 1 multiple interactions ISO [Tadalafil co-treated with Thioacetamide] results in increased expression of PRKG1 protein; Tadalafil inhibits the reaction [Streptozocin results in decreased expression of PRKG1 protein] CTD PMID:31323263 PMID:34428446 NCBI chr 1:228,409,605...229,638,794
Ensembl chr 1:228,408,947...229,639,080 		JBrowse link
G Prkg2 protein kinase cGMP-dependent 2 increases expression ISO Tadalafil results in increased expression of PRKG2 mRNA CTD PMID:32513693 NCBI chr14:10,559,882...10,668,479
Ensembl chr14:10,559,882...10,666,888 		JBrowse link
G Rela RELA proto-oncogene, NF-kB subunit multiple interactions ISO Tadalafil inhibits the reaction [Streptozocin results in increased expression of RELA protein modified form]; Tadalafil inhibits the reaction [Thioacetamide results in increased phosphorylation of RELA protein] CTD PMID:31323263 PMID:34428446 NCBI chr 1:202,925,001...202,935,484
Ensembl chr 1:202,924,945...202,935,484 		JBrowse link
G Slc2a1 solute carrier family 2 member 1 multiple interactions EXP Tadalafil inhibits the reaction [Aflatoxin B1 results in increased expression of SLC2A1 mRNA] CTD PMID:35608386 NCBI chr 5:132,717,196...132,745,416
Ensembl chr 5:132,717,196...132,745,416 		JBrowse link
G Syp synaptophysin multiple interactions ISO Tadalafil inhibits the reaction [Thioacetamide results in decreased expression of SYP protein] CTD PMID:31323263 NCBI chr  X:14,849,444...14,864,553
Ensembl chr  X:14,849,444...14,864,745 		JBrowse link
G Tgfb1 transforming growth factor, beta 1 multiple interactions EXP Tadalafil inhibits the reaction [[Aflatoxin B1 co-treated with Ethanol] results in increased expression of TGFB1 mRNA] CTD PMID:35608386 NCBI chr 1:81,196,532...81,212,848
Ensembl chr 1:81,196,532...81,212,847 		JBrowse link
G Tnf tumor necrosis factor multiple interactions
decreases expression		 EXP
ISO		 Tadalafil inhibits the reaction [Cisplatin results in increased expression of TNF protein]; Tadalafil inhibits the reaction [Oxygen deficiency results in increased expression of TNF mRNA]; zinc protoporphyrin inhibits the reaction [Tadalafil inhibits the reaction [Cisplatin results in increased expression of TNF protein]]
Tadalafil results in decreased expression of TNF mRNA
Tadalafil inhibits the reaction [Thioacetamide results in increased expression of TNF protein]		 CTD PMID:16368379 PMID:31323263 PMID:32621855 NCBI chr20:3,622,011...3,624,629
Ensembl chr20:3,622,011...3,624,629 		JBrowse link
G Vegfa vascular endothelial growth factor A multiple interactions EXP Tadalafil inhibits the reaction [Aflatoxin B1 results in increased expression of VEGFA mRNA] CTD PMID:35608386 NCBI chr 9:14,955,300...14,970,641
Ensembl chr 9:14,955,300...14,970,641 		JBrowse link
G Wnt3a Wnt family member 3A multiple interactions ISO Tadalafil inhibits the reaction [Streptozocin results in decreased expression of WNT3A protein] CTD PMID:34428446 NCBI chr10:44,034,174...44,078,366
Ensembl chr10:44,034,194...44,078,324 		JBrowse link
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