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: artesunate
Accession: CHEBI:63918
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Definition: An artemisinin derivative that is the hemisuccinate ester of the lactol resulting from the reduction of the lactone carbonyl group of artemisinin. It is used, generally as the sodium salt, for the treatment of malaria.
Synonyms: exact_synonym: 4-oxo-4-{[(3R,5aS,6R,8aS,9R,10S,12R,12aR)-3,6,9-trimethyldecahydro-3,12-epoxypyrano[4,3-j][1,2]benzodioxepin-10-yl]oxy}butanoic acid
related_synonym: AS; Formula=C19H28O8; InChI=1S/C19H28O8/c1-10-4-5-13-11(2)16(23-15(22)7-6-14(20)21)24-17-19(13)12(10)8-9-18(3,25-17)26-27-19/h10-13,16-17H,4-9H2,1-3H3,(H,20,21)/t10-,11-,12+,13+,16-,17-,18-,19-/m1/s1; InChIKey=FIHJKUPKCHIPAT-AHIGJZGOSA-N; SMILES=[H][C@@]12CC[C@@]3(C)OO[C@@]11[C@@]([H])(CC[C@H]2C)[C@@H](C)[C@H](OC(=O)CCC(O)=O)O[C@]1([H])O3; artesunato; artesunatum; artesunic acid; butanedioic acid, 1-[(3R,5aS,6R,8aS,9R,10S,12R,12aR)-decahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin-10-yl] ester; dihydroqinghasu hemsuccinate
alt_id: MESH:C039726
xref: CAS:182824-33-5; CAS:88495-63-0; Drug_Central:247; KEGG:D02482
xref_mesh: MESH:C039726
xref: Reaxys:6003212; Wikipedia:Artesunate
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Acta2
actin, alpha 2, smooth muscle, aorta
multiple interactions decreases expression
EXP ISO
Artesunate inhibits the reaction [Carbon Tetrachloride results in increased expression of ACTA2 protein] Artesunate results in decreased expression of ACTA2 mRNA; Artesunate results in decreased expression of ACTA2 protein Deferoxamine inhibits the reaction [Artesunate results in decreased expression of ACTA2 mRNA]
CTD
PMID:30551460
NCBI chr19:34,240,336...34,255,585
Ensembl chr19:34,241,090...34,255,590
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Aifm1
apoptosis-inducing factor, mitochondrion-associated 1
affects localization
ISO
artesunate affects the localization of AIFM1 protein
CTD
PMID:24704559
NCBI chr X:48,474,944...48,513,563
Ensembl chr X:48,474,944...48,513,563
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Ar
androgen receptor
multiple interactions
ISO
artesunate binds to and results in decreased activity of AR protein
CTD
PMID:25752796
NCBI chr X:98,148,757...98,323,218
Ensembl chr X:98,148,769...98,323,215
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Atg12
autophagy related 12
increases expression
ISO
Artesunate results in increased expression of ATG12 mRNA
CTD
PMID:30551460
NCBI chr18:46,732,417...46,741,724
Ensembl chr18:46,730,144...46,741,580
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Atg3
autophagy related 3
increases expression
ISO
Artesunate results in increased expression of ATG3 mRNA
CTD
PMID:30551460
NCBI chr16:45,158,829...45,188,538
Ensembl chr16:45,158,785...45,188,538
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Atg5
autophagy related 5
increases expression
ISO
Artesunate results in increased expression of ATG5 mRNA
CTD
PMID:30551460
NCBI chr10:44,268,322...44,364,299
Ensembl chr10:44,268,358...44,364,291
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Bax
BCL2-associated X protein
increases expression multiple interactions
ISO
artesunate results in increased expression of BAX protein [1,2-Dimethylhydrazine co-treated with artesunate] results in increased expression of BAX protein
CTD
PMID:24704559 PMID:29031619
NCBI chr 7:45,461,695...45,466,903
Ensembl chr 7:45,461,697...45,466,898
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Bcl2
B cell leukemia/lymphoma 2
decreases expression multiple interactions
ISO
artesunate results in decreased expression of BCL2 protein [1,2-Dimethylhydrazine co-treated with artesunate] results in decreased expression of BCL2 protein
CTD
PMID:24704559 PMID:29031619
NCBI chr 1:106,538,176...106,714,290
Ensembl chr 1:106,538,178...106,714,274
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Bst1
bone marrow stromal cell antigen 1
increases response to substance
ISO
BST1 mRNA results in increased susceptibility to artesunate
CTD
PMID:20144594
NCBI chr 5:43,818,880...43,843,468
Ensembl chr 5:43,818,885...43,843,986
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Casp3
caspase 3
increases activity
ISO
artesunate results in increased activity of CASP3 protein
CTD
PMID:19513562 PMID:24704559
NCBI chr 8:46,617,291...46,639,698
Ensembl chr 8:46,617,291...46,639,689
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Casp9
caspase 9
affects expression
ISO
artesunate affects the expression of CASP9 protein
CTD
PMID:24704559
NCBI chr 4:141,793,612...141,815,978
Ensembl chr 4:141,793,612...141,815,976
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Cat
catalase
increases expression decreases response to substance
ISO
artesunate results in increased expression of CAT protein CAT protein results in decreased susceptibility to artesunate
CTD
PMID:19513562 PMID:20144594
NCBI chr 2:103,453,904...103,485,153
Ensembl chr 2:103,453,849...103,485,160
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Cct2
chaperonin containing Tcp1, subunit 2 (beta)
decreases response to substance
ISO
CCT2 mRNA results in decreased susceptibility to artesunate
CTD
PMID:20144594
NCBI chr10:117,050,997...117,063,852
Ensembl chr10:117,051,001...117,063,814
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Chek1
checkpoint kinase 1
increases phosphorylation multiple interactions
ISO
Artesunate results in increased phosphorylation of CHEK1 protein APOBEC3C protein promotes the reaction [Artesunate results in increased phosphorylation of CHEK1 protein]
CTD
PMID:31664825
NCBI chr 9:36,708,482...36,726,658
Ensembl chr 9:36,708,482...36,727,065
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Chek2
checkpoint kinase 2
multiple interactions increases phosphorylation
ISO
APOBEC3C protein promotes the reaction [Artesunate results in increased phosphorylation of CHEK2 protein]
CTD
PMID:31664825
NCBI chr 5:110,839,800...110,874,140
Ensembl chr 5:110,839,979...110,874,145
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Clip4
CAP-GLY domain containing linker protein family, member 4
increases response to substance
ISO
CLIP4 mRNA results in increased susceptibility to artesunate
CTD
PMID:20144594
NCBI chr17:71,769,674...71,864,210
Ensembl chr17:71,768,473...71,864,273
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Coq8a
coenzyme Q8A
decreases response to substance
ISO
COQ8A mRNA results in decreased susceptibility to artesunate
CTD
PMID:20144594
NCBI chr 1:180,165,238...180,196,020
Ensembl chr 1:180,165,238...180,199,602
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Ctnnb1
catenin (cadherin associated protein), beta 1
multiple interactions
ISO
artesunate inhibits the reaction [1,2-Dimethylhydrazine results in increased expression of CTNNB1 protein]
CTD
PMID:29031619
NCBI chr 9:120,933,400...120,960,507
Ensembl chr 9:120,929,216...120,960,507
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Cyp2a5
cytochrome P450, family 2, subfamily a, polypeptide 5
affects metabolic processing
ISO
CYP2A6 protein affects the metabolism of Artesunate
CTD
PMID:12920490
NCBI chr 7:26,835,339...26,843,264
Ensembl chr 7:26,835,305...26,843,548
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Dbh
dopamine beta hydroxylase
increases response to substance
ISO
DBH mRNA results in increased susceptibility to artesunate
CTD
PMID:20144594
NCBI chr 2:27,165,507...27,183,204
Ensembl chr 2:27,165,233...27,183,200
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Des
desmin
decreases expression multiple interactions
ISO
Artesunate results in decreased expression of DES mRNA; Artesunate results in decreased expression of DES protein Deferoxamine inhibits the reaction [Artesunate results in decreased expression of DES mRNA]
CTD
PMID:30551460
NCBI chr 1:75,360,292...75,368,579
Ensembl chr 1:75,360,329...75,368,579
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Esr1
estrogen receptor 1 (alpha)
multiple interactions
ISO
artesunate binds to and results in decreased activity of ESR1 protein
CTD
PMID:25752796
NCBI chr10:4,611,989...5,005,633
Ensembl chr10:4,611,593...5,005,614
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Fas
Fas (TNF receptor superfamily member 6)
increases expression
ISO
artesunate results in increased expression of FAS protein
CTD
PMID:19513562
NCBI chr19:34,290,647...34,327,775
Ensembl chr19:34,290,666...34,327,772
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Flna
filamin, alpha
increases response to substance
ISO
FLNA mRNA results in increased susceptibility to artesunate
CTD
PMID:20144594
NCBI chr X:74,223,461...74,249,854
Ensembl chr X:74,223,461...74,249,820
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Fn1
fibronectin 1
multiple interactions decreases expression
ISO
Deferoxamine inhibits the reaction [Artesunate results in decreased expression of FN1 mRNA] Artesunate results in decreased expression of FN1 mRNA; Artesunate results in decreased expression of FN1 protein
CTD
PMID:30551460
NCBI chr 1:71,585,473...71,653,280
Ensembl chr 1:71,585,520...71,653,200
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Fth1
ferritin heavy polypeptide 1
decreases expression multiple interactions
ISO
Artesunate results in decreased expression of FTH1 mRNA; Artesunate results in decreased expression of FTH1 protein Chloroquine inhibits the reaction [Artesunate results in decreased expression of FTH1 mRNA]
CTD
PMID:30551460
NCBI chr19:9,980,600...9,985,111
Ensembl chr19:9,980,598...9,985,098
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Fzd7
frizzled class receptor 7
increases response to substance
ISO
FZD7 mRNA results in increased susceptibility to artesunate
CTD
PMID:20144594
NCBI chr 1:59,482,147...59,486,955
Ensembl chr 1:59,482,424...59,486,955
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Gclc
glutamate-cysteine ligase, catalytic subunit
affects response to substance decreases response to substance
ISO
GCLC mRNA affects the susceptibility to artesunate GCLC mRNA results in decreased susceptibility to artesunate
CTD
PMID:15796179
NCBI chr 9:77,754,535...77,794,489
Ensembl chr 9:77,754,535...77,794,485
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Gclm
glutamate-cysteine ligase, modifier subunit
decreases response to substance
ISO
GCLM mRNA results in decreased susceptibility to artesunate
CTD
PMID:15796179
NCBI chr 3:122,245,487...122,267,215
Ensembl chr 3:122,245,557...122,270,732
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Gpx4
glutathione peroxidase 4
multiple interactions decreases activity
EXP ISO
Artesunate inhibits the reaction [Carbon Tetrachloride results in increased expression of GPX4 protein] Artesunate results in decreased activity of GPX4 protein
CTD
PMID:30551460
NCBI chr10:80,047,166...80,056,439
Ensembl chr10:80,047,166...80,056,439
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Gstm4
glutathione S-transferase, mu 4
affects response to substance
ISO
GSTM4 mRNA affects the susceptibility to artesunate
CTD
PMID:15796179
NCBI chr 3:108,030,571...108,045,179
Ensembl chr 3:108,040,408...108,044,894
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Gstp1
glutathione S-transferase, pi 1
decreases expression
ISO
artesunate results in decreased expression of GSTP1 protein
CTD
PMID:19513562
NCBI chr19:4,035,411...4,037,912
Ensembl chr19:4,035,407...4,037,985
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Gstz1
glutathione transferase zeta 1 (maleylacetoacetate isomerase)
affects response to substance
ISO
GSTZ1 mRNA affects the susceptibility to artesunate
CTD
PMID:15796179
NCBI chr12:87,147,161...87,164,723
Ensembl chr12:87,147,165...87,164,723
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Il1b
interleukin 1 beta
multiple interactions
ISO
artesunate inhibits the reaction [Ethanol results in increased expression of IL1B protein]; artesunate inhibits the reaction [Glucose results in increased expression of IL1B mRNA]; artesunate inhibits the reaction [Glucose results in increased secretion of IL1B protein]
CTD
PMID:27474069 PMID:30031708
NCBI chr 2:129,364,569...129,371,164
Ensembl chr 2:129,364,570...129,371,139
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Il6
interleukin 6
multiple interactions
ISO
Artesunate inhibits the reaction [Ethanol results in increased expression of IL6 protein]; Artesunate inhibits the reaction [Glucose results in increased expression of IL6 mRNA]; Artesunate inhibits the reaction [Glucose results in increased secretion of IL6 protein]
CTD
PMID:27474069 PMID:30031708
NCBI chr 5:30,013,114...30,019,975
Ensembl chr 5:30,013,114...30,019,981
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Itgb1
integrin beta 1 (fibronectin receptor beta)
increases response to substance
ISO
ITGB1 mRNA results in increased susceptibility to artesunate
CTD
PMID:20144594
NCBI chr 8:128,685,654...128,733,579
Ensembl chr 8:128,685,654...128,733,200
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Mgst3
microsomal glutathione S-transferase 3
affects response to substance
ISO
MGST3 mRNA affects the susceptibility to artesunate
CTD
PMID:15796179
NCBI chr 1:167,371,966...167,393,841
Ensembl chr 1:167,371,966...167,393,841
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Mki67
antigen identified by monoclonal antibody Ki 67
multiple interactions
ISO
artesunate inhibits the reaction [1,2-Dimethylhydrazine results in increased expression of MKI67 protein]
CTD
PMID:29031619
NCBI chr 7:135,689,784...135,716,450
Ensembl chr 7:135,689,784...135,716,361
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Mmp9
matrix metallopeptidase 9
multiple interactions decreases expression
ISO
artesunate inhibits the reaction [1,2-Dimethylhydrazine results in increased expression of MMP9 protein] Chloroquine inhibits the reaction [Artesunate results in decreased expression of MMP9 mRNA]
CTD
PMID:29031619 PMID:30551460
NCBI chr 2:164,940,326...164,955,850
Ensembl chr 2:164,940,780...164,955,850
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Mpo
myeloperoxidase
multiple interactions
ISO
artesunate inhibits the reaction [Ethanol results in increased activity of MPO protein]
CTD
PMID:27474069
NCBI chr11:87,793,784...87,804,412
Ensembl chr11:87,793,581...87,804,413
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Mthfd2
methylenetetrahydrofolate dehydrogenase (NAD+ dependent), methenyltetrahydrofolate cyclohydrolase
decreases response to substance
ISO
MTHFD2 mRNA results in decreased susceptibility to artesunate
CTD
PMID:20144594
NCBI chr 6:83,305,704...83,326,011
Ensembl chr 6:83,305,691...83,325,908
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Myd88
myeloid differentiation primary response gene 88
multiple interactions
ISO
artesunate inhibits the reaction [Glucose results in increased expression of MYD88 protein]
CTD
PMID:30031708
NCBI chr 9:119,335,934...119,340,018
Ensembl chr 9:119,335,934...119,341,411
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Naca
nascent polypeptide-associated complex alpha polypeptide
decreases response to substance
ISO
NACA mRNA results in decreased susceptibility to artesunate
CTD
PMID:20144594
NCBI chr10:128,035,346...128,048,637
Ensembl chr10:128,035,575...128,048,637
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Nckap1
NCK-associated protein 1
increases response to substance
ISO
NCKAP1 mRNA results in increased susceptibility to artesunate
CTD
PMID:20144594
NCBI chr 2:80,500,512...80,581,182
Ensembl chr 2:80,500,512...80,581,380
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Ncoa4
nuclear receptor coactivator 4
multiple interactions decreases expression
ISO
Chloroquine inhibits the reaction [Artesunate results in decreased expression of NCOA4 mRNA] Artesunate results in decreased expression of NCOA4 mRNA; Artesunate results in decreased expression of NCOA4 protein
CTD
PMID:30551460
NCBI chr14:32,159,879...32,179,855
Ensembl chr14:32,159,865...32,179,855
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Nfe2l2
nuclear factor, erythroid derived 2, like 2
affects localization
ISO
artesunate affects the localization of NFE2L2 protein
CTD
PMID:26340163
NCBI chr 2:75,675,513...75,704,663
Ensembl chr 2:75,675,513...75,704,641
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Nlrp3
NLR family, pyrin domain containing 3
multiple interactions
ISO
artesunate inhibits the reaction [Glucose results in increased expression of NLRP3 protein]
CTD
PMID:30031708
NCBI chr11:59,541,569...59,566,955
Ensembl chr11:59,541,568...59,566,956
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Parp1
poly (ADP-ribose) polymerase family, member 1
increases cleavage
ISO
artesunate results in increased cleavage of PARP1 protein
CTD
PMID:24704559
NCBI chr 1:180,568,891...180,600,999
Ensembl chr 1:180,568,924...180,601,254
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Pcna
proliferating cell nuclear antigen
multiple interactions
ISO
artesunate inhibits the reaction [1,2-Dimethylhydrazine results in increased expression of PCNA protein]
CTD
PMID:29031619
NCBI chr 2:132,249,286...132,253,180
Ensembl chr 2:132,249,162...132,253,314
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Pgr
progesterone receptor
multiple interactions
ISO
artesunate binds to and results in increased activity of PGR protein
CTD
PMID:25752796
NCBI chr 9:8,898,900...8,968,611
Ensembl chr 9:8,899,833...8,968,611
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Ptgs2
prostaglandin-endoperoxide synthase 2
multiple interactions
EXP
[Carbon Tetrachloride results in increased susceptibility to Artesunate] which results in increased expression of PTGS2 mRNA; [Carbon Tetrachloride results in increased susceptibility to Artesunate] which results in increased expression of PTGS2 protein
CTD
PMID:30551460
NCBI chr 1:150,100,031...150,108,234
Ensembl chr 1:150,100,031...150,108,227
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Rela
v-rel reticuloendotheliosis viral oncogene homolog A (avian)
multiple interactions
ISO
artesunate inhibits the reaction [Ethanol results in increased expression of RELA protein]; artesunate inhibits the reaction [Glucose results in increased phosphorylation of RELA protein]
CTD
PMID:27474069 PMID:30031708
NCBI chr19:5,637,442...5,648,134
Ensembl chr19:5,637,483...5,648,130
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Rpa2
replication protein A2
increases phosphorylation
ISO
Artesunate results in increased phosphorylation of RPA2 protein
CTD
PMID:31664825
NCBI chr 4:132,768,360...132,778,746
Ensembl chr 4:132,768,332...132,778,752
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Rpl41
ribosomal protein L41
decreases response to substance
ISO
RPL41 mRNA results in decreased susceptibility to artesunate
CTD
PMID:20144594
NCBI chr10:128,548,110...128,549,168
Ensembl chr10:128,548,114...128,549,305
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Rpl6
ribosomal protein L6
decreases response to substance
ISO
RPL6 mRNA results in decreased susceptibility to artesunate
CTD
PMID:20144594
NCBI chr 5:121,204,501...121,209,241
Ensembl chr 5:121,204,481...121,209,241
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Rpl7
ribosomal protein L7
decreases response to substance
ISO
RPL7 mRNA results in decreased susceptibility to artesunate
CTD
PMID:20144594
NCBI chr 1:16,101,295...16,104,433
Ensembl chr 1:16,101,295...16,104,662
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Rps12
ribosomal protein S12
decreases response to substance
ISO
RPS12 mRNA results in decreased susceptibility to artesunate
CTD
PMID:20144594
NCBI chr10:23,785,183...23,787,383
Ensembl chr10:23,785,183...23,787,275
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Rps15a
ribosomal protein S15A
decreases response to substance
ISO
RPS15A mRNA results in decreased susceptibility to artesunate
CTD
PMID:20144594
NCBI chr 7:118,104,374...118,116,147
Ensembl chr 7:118,104,372...118,116,188
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Rps6
ribosomal protein S6
decreases response to substance
ISO
RPS6 mRNA results in decreased susceptibility to artesunate
CTD
PMID:20144594
NCBI chr 4:86,854,099...86,857,367
Ensembl chr 4:86,854,660...86,857,412
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Slc25a19
solute carrier family 25 (mitochondrial thiamine pyrophosphate carrier), member 19
decreases response to substance
ISO
SLC25A19 mRNA results in decreased susceptibility to artesunate
CTD
PMID:20144594
NCBI chr11:115,614,165...115,628,296
Ensembl chr11:115,614,178...115,628,295
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Sp1
trans-acting transcription factor 1
decreases expression
ISO
artesunate results in decreased expression of SP1 protein
CTD
PMID:19513562
NCBI chr15:102,406,316...102,436,404
Ensembl chr15:102,406,143...102,436,404
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Sqstm1
sequestosome 1
decreases expression multiple interactions
ISO
Artesunate results in decreased expression of SQSTM1 mRNA; Artesunate results in decreased expression of SQSTM1 protein Chloroquine inhibits the reaction [Artesunate results in decreased expression of SQSTM1 protein]
CTD
PMID:30551460
NCBI chr11:50,200,152...50,210,820
Ensembl chr11:50,199,366...50,210,827
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Srsf2
serine and arginine-rich splicing factor 2
decreases response to substance
ISO
SRSF2 mRNA results in decreased susceptibility to artesunate
CTD
PMID:20144594
NCBI chr11:116,849,897...116,853,675
Ensembl chr11:116,849,901...116,853,094
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Timp1
tissue inhibitor of metalloproteinase 1
multiple interactions increases expression
ISO
Chloroquine inhibits the reaction [Artesunate results in increased expression of TIMP1 mRNA]
CTD
PMID:30551460
NCBI chr X:20,870,166...20,874,737
Ensembl chr X:20,870,166...20,874,735
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Tlr4
toll-like receptor 4
multiple interactions
ISO
artesunate inhibits the reaction [Glucose results in increased expression of TLR4 protein]
CTD
PMID:30031708
NCBI chr 4:66,827,551...66,846,581
Ensembl chr 4:66,827,584...66,930,284
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Tnf
tumor necrosis factor
multiple interactions
ISO
artesunate inhibits the reaction [Ethanol results in increased expression of TNF protein]; artesunate inhibits the reaction [Glucose results in increased expression of TNF mRNA]; artesunate inhibits the reaction [Glucose results in increased secretion of TNF protein]
CTD
PMID:27474069 PMID:30031708
NCBI chr17:35,199,367...35,202,007
Ensembl chr17:35,199,381...35,202,007
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Tpt1
tumor protein, translationally-controlled 1
affects response to substance
ISO
TPT1 protein affects the susceptibility to artesunate
CTD
PMID:15878303
NCBI chr14:75,845,256...75,848,303
Ensembl chr14:75,845,093...75,848,525
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Tufm
Tu translation elongation factor, mitochondrial
decreases response to substance
ISO
TUFM mRNA results in decreased susceptibility to artesunate
CTD
PMID:20144594
NCBI chr 7:126,487,271...126,490,731
Ensembl chr 7:126,487,361...126,490,731
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Vegfa
vascular endothelial growth factor A
multiple interactions
ISO
artesunate inhibits the reaction [1,2-Dimethylhydrazine results in increased expression of VEGFA protein]
CTD
PMID:29031619
NCBI chr17:46,016,993...46,032,377
Ensembl chr17:46,016,993...46,032,369
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Yy1
YY1 transcription factor
decreases expression
ISO
artesunate results in decreased expression of YY1 protein
CTD
PMID:19513562
NCBI chr12:108,792,945...108,820,148
Ensembl chr12:108,792,973...108,820,148
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Zbtb4
zinc finger and BTB domain containing 4
increases response to substance
ISO
ZBTB4 mRNA results in increased susceptibility to artesunate
CTD
PMID:20144594
NCBI chr11:69,765,912...69,784,026
Ensembl chr11:69,765,912...69,784,023
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