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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:kenpaullone
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Accession:CHEBI:92658 term browser browse the term
Definition:An indolobenzazepine that is paullone in which the hydrogen at position 9 is replaced by a bromo substituent. It is an ATP-competitive inhibitor of cyclin-dependent kinases (CDKs) and glycogen synthase kinase 3beta (GSK3beta).
Synonyms:exact_synonym: 9-bromo-7,12-dihydroindolo[3,2-d][1]benzazepin-6(5H)-one
 related_synonym: 9-bromopaullone;   Formula=C16H11BrN2O;   InChI=1S/C16H11BrN2O/c17-9-5-6-14-11(7-9)12-8-15(20)18-13-4-2-1-3-10(13)16(12)19-14/h1-7,19H,8H2,(H,18,20);   InChIKey=QQUXFYAWXPMDOE-UHFFFAOYSA-N;   SMILES=BrC1=CC2=C(NC3=C2CC(=O)NC2=CC=CC=C32)C=C1
 xref: CAS:142273-20-9;   Chemspider:3688;   LINCS:LSM-2824
 xref_mesh: MESH:C119620
 xref: PMCID:PMC6216549;   PMCID:PMC8551327;   PMID:10425100;   PMID:16122578;   PMID:16499355;   PMID:24134630;   PMID:24978614;   PMID:25616642;   PMID:27008992;   PMID:28955831;   PMID:29128602;   PMID:29514916;   PMID:29577900;   PMID:30038266;   PMID:31296906;   PMID:31911436;   PMID:33410342;   Reaxys:5346108


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kenpaullone term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Abcb1a ATP binding cassette subfamily B member 1A increases expression ISO kenpaullone results in increased expression of ABCB1 protein CTD PMID:18624906 NCBI chr 4:25,357,467...25,529,941
Ensembl chr 4:25,158,362...25,442,709 		JBrowse link
G Adm adrenomedullin decreases expression EXP kenpaullone results in decreased expression of ADM mRNA CTD PMID:17993264 NCBI chr 1:164,745,484...164,747,655
Ensembl chr 1:164,745,466...164,747,654 		JBrowse link
G Ar androgen receptor affects localization
increases activity		 ISO kenpaullone analog affects the localization of AR protein
kenpaullone analog results in increased activity of AR protein		 CTD PMID:21111724 NCBI chr  X:63,104,771...63,273,934
Ensembl chr  X:63,104,771...63,273,925 		JBrowse link
G Bmp6 bone morphogenetic protein 6 multiple interactions ISO kenpaullone inhibits the reaction [BMP6 protein results in increased secretion of HAMP protein modified form] CTD PMID:25633564 NCBI chr17:26,318,121...26,469,691
Ensembl chr17:26,318,569...26,470,365 		JBrowse link
G Bmpr2 bone morphogenetic protein receptor type 2 increases expression ISO kenpaullone results in increased expression of BMPR2 mRNA CTD PMID:25633564 NCBI chr 9:61,192,718...61,307,280
Ensembl chr 9:61,190,566...61,301,809 		JBrowse link
G Casp3 caspase 3 multiple interactions ISO kenpaullone inhibits the reaction [fipronil results in increased activity of CASP3 protein] CTD PMID:21296133 NCBI chr16:45,662,910...45,681,171
Ensembl chr16:45,662,910...45,684,648 		JBrowse link
G Ccng2 cyclin G2 decreases expression EXP kenpaullone results in decreased expression of CCNG2 mRNA CTD PMID:17993264 NCBI chr14:14,804,321...14,812,819
Ensembl chr14:14,804,322...14,812,830 		JBrowse link
G Cdk2 cyclin dependent kinase 2 decreases activity ISO kenpaullone results in decreased activity of CDK2 protein CTD PMID:12534346 NCBI chr 7:1,129,878...1,137,431
Ensembl chr 7:1,129,811...1,137,403 		JBrowse link
G Cited2 Cbp/p300-interacting transactivator, with Glu/Asp-rich carboxy-terminal domain, 2 decreases expression EXP kenpaullone results in decreased expression of CITED2 mRNA CTD PMID:17993264 NCBI chr 1:12,312,426...12,314,869
Ensembl chr 1:12,312,160...12,314,897 		JBrowse link
G Ctnnb1 catenin beta 1 affects localization ISO kenpaullone analog affects the localization of CTNNB1 protein CTD PMID:21111724 NCBI chr 8:120,640,008...120,667,110
Ensembl chr 8:120,639,995...120,667,111 		JBrowse link
G Ddit4 DNA-damage-inducible transcript 4 decreases expression EXP kenpaullone results in decreased expression of DDIT4 mRNA CTD PMID:17993264 NCBI chr20:27,891,989...27,894,088
Ensembl chr20:27,891,998...27,894,105 		JBrowse link
G Dusp1 dual specificity phosphatase 1 decreases expression EXP kenpaullone results in decreased expression of DUSP1 mRNA CTD PMID:17993264 NCBI chr10:16,680,478...16,683,275 JBrowse link
G Errfi1 ERBB receptor feedback inhibitor 1 decreases expression EXP kenpaullone results in decreased expression of ERRFI1 mRNA CTD PMID:17993264 NCBI chr 5:161,323,981...161,337,289
Ensembl chr 5:161,323,998...161,337,282 		JBrowse link
G Exo1 exonuclease 1 decreases expression EXP kenpaullone results in decreased expression of EXO1 mRNA CTD PMID:17993264 NCBI chr13:87,809,725...87,834,654
Ensembl chr13:87,809,810...87,834,654 		JBrowse link
G Fos Fos proto-oncogene, AP-1 transcription factor subunit increases expression EXP kenpaullone results in increased expression of FOS mRNA CTD PMID:17993264 NCBI chr 6:105,121,170...105,124,036
Ensembl chr 6:105,121,170...105,124,036 		JBrowse link
G Fosb FosB proto-oncogene, AP-1 transcription factor subunit increases expression EXP kenpaullone results in increased expression of FOSB mRNA CTD PMID:17993264 NCBI chr 1:78,954,312...78,961,492
Ensembl chr 1:78,954,115...78,961,465 		JBrowse link
G Furin furin (paired basic amino acid cleaving enzyme) decreases expression ISO kenpaullone results in decreased expression of FURIN mRNA CTD PMID:25633564 NCBI chr 1:134,348,142...134,361,182
Ensembl chr 1:134,348,144...134,364,314 		JBrowse link
G Fzd8 frizzled class receptor 8 decreases expression EXP kenpaullone results in decreased expression of FZD8 mRNA CTD PMID:17993264 NCBI chr17:57,312,924...57,320,551
Ensembl chr17:57,314,450...57,320,650 		JBrowse link
G Gadd45b growth arrest and DNA-damage-inducible, beta decreases expression EXP kenpaullone results in decreased expression of GADD45B mRNA CTD PMID:17993264 NCBI chr 7:8,778,004...8,780,306
Ensembl chr 7:8,778,007...8,780,046 		JBrowse link
G Giot1 gonadotropin inducible ovarian transcription factor 1 decreases expression EXP kenpaullone results in decreased expression of GIOT1 mRNA CTD PMID:17993264 NCBI chr 7:10,215,602...10,236,423
Ensembl chr 7:10,202,982...10,237,099 		JBrowse link
G Gsk3a glycogen synthase kinase 3 alpha decreases phosphorylation EXP kenpaullone results in decreased phosphorylation of GSK3A protein CTD PMID:17993264 NCBI chr 1:80,815,843...80,825,732
Ensembl chr 1:80,815,850...80,825,802 		JBrowse link
G Gsk3b glycogen synthase kinase 3 beta multiple interactions
decreases phosphorylation
decreases activity		 ISO
EXP		 kenpaullone inhibits the reaction [fipronil results in decreased phosphorylation of GSK3B protein]
kenpaullone results in decreased phosphorylation of GSK3B protein
kenpaullone results in decreased activity of GSK3B protein		 CTD PMID:12534346 PMID:17993264 PMID:21111724 PMID:21296133 NCBI chr11:62,498,997...62,648,665
Ensembl chr11:62,504,316...62,648,646 		JBrowse link
G Hamp hepcidin antimicrobial peptide decreases expression
multiple interactions
decreases secretion		 ISO kenpaullone results in decreased expression of HAMP mRNA
kenpaullone inhibits the reaction [BMP6 protein results in increased secretion of HAMP protein modified form]; kenpaullone inhibits the reaction [IL6 protein results in increased expression of HAMP mRNA]
kenpaullone results in decreased secretion of HAMP protein modified form		 CTD PMID:25633564 NCBI chr 1:86,170,926...86,172,865
Ensembl chr 1:86,170,901...86,172,891 		JBrowse link
G Hoxa1 homeobox A1 increases expression ISO kenpaullone results in increased expression of HOXA1 CTD PMID:26820057 NCBI chr 4:81,255,814...81,258,587
Ensembl chr 4:81,255,883...81,258,504 		JBrowse link
G Il6 interleukin 6 multiple interactions ISO kenpaullone inhibits the reaction [IL6 protein results in increased expression of HAMP mRNA] CTD PMID:25633564 NCBI chr 4:5,214,602...5,219,178
Ensembl chr 4:5,213,394...5,219,178 		JBrowse link
G Isl2 ISL LIM homeobox 2 increases expression EXP kenpaullone results in increased expression of ISL2 mRNA CTD PMID:17993264 NCBI chr 8:55,923,805...55,928,790
Ensembl chr 8:55,923,805...55,928,790 		JBrowse link
G Junb JunB proto-oncogene, AP-1 transcription factor subunit increases expression EXP kenpaullone results in increased expression of JUNB protein CTD PMID:17993264 NCBI chr19:23,176,265...23,178,049
Ensembl chr19:23,176,294...23,178,035 		JBrowse link
G Klf6 KLF transcription factor 6 decreases expression EXP kenpaullone results in decreased expression of KLF6 mRNA CTD PMID:17993264 NCBI chr17:64,539,456...64,548,451
Ensembl chr17:64,531,463...64,588,570 		JBrowse link
G Klk1c10 kallikrein 1-related peptidase C10 increases expression ISO kenpaullone results in increased expression of KLK3 mRNA CTD PMID:21111724 NCBI chr 1:94,402,993...94,407,052
Ensembl chr 1:94,402,993...94,407,052 		JBrowse link
G Lck LCK proto-oncogene, Src family tyrosine kinase decreases activity ISO kenpaullone results in decreased activity of LCK protein CTD PMID:12534346 NCBI chr 5:141,888,318...141,916,945
Ensembl chr 5:141,888,326...141,903,794 		JBrowse link
G Lif LIF, interleukin 6 family cytokine increases expression EXP kenpaullone results in increased expression of LIF mRNA CTD PMID:17993264 NCBI chr14:79,131,049...79,140,486
Ensembl chr14:79,134,574...79,140,482 		JBrowse link
G Mex3b mex-3 RNA binding family member B decreases expression EXP kenpaullone results in decreased expression of MEX3B mRNA CTD PMID:17993264 NCBI chr 1:136,855,130...136,859,365
Ensembl chr 1:136,855,130...136,859,354 		JBrowse link
G Nppa natriuretic peptide A multiple interactions EXP kenpaullone promotes the reaction [Phenylephrine results in increased expression of NPPA mRNA] CTD PMID:25341891 NCBI chr 5:158,429,042...158,430,351
Ensembl chr 5:158,429,042...158,430,351 		JBrowse link
G Nr4a1 nuclear receptor subfamily 4, group A, member 1 increases expression EXP kenpaullone results in increased expression of NR4A1 mRNA CTD PMID:17993264 NCBI chr 7:132,368,399...132,389,300
Ensembl chr 7:132,374,840...132,389,297 		JBrowse link
G Pfkfb3 6-phosphofructo-2-kinase/fructose-2,6-biphosphatase 3 decreases expression EXP kenpaullone results in decreased expression of PFKFB3 mRNA CTD PMID:17993264 NCBI chr17:66,983,629...67,064,702
Ensembl chr17:66,983,686...67,063,125 		JBrowse link
G Pnrc1 proline-rich nuclear receptor coactivator 1 decreases expression EXP kenpaullone results in decreased expression of PNRC1 mRNA CTD PMID:17993264 NCBI chr 5:47,647,070...47,657,832
Ensembl chr 5:47,647,071...47,650,161 		JBrowse link
G Ppp1r3b protein phosphatase 1, regulatory subunit 3B decreases expression EXP kenpaullone results in decreased expression of PPP1R3B mRNA CTD PMID:17993264 NCBI chr16:56,830,011...56,842,395
Ensembl chr16:56,829,660...56,842,406 		JBrowse link
G Ptger4 prostaglandin E receptor 4 decreases expression EXP kenpaullone results in decreased expression of PTGER4 mRNA CTD PMID:17993264 NCBI chr 2:54,330,563...54,347,451
Ensembl chr 2:54,335,424...54,346,670 		JBrowse link
G Ptgs2 prostaglandin-endoperoxide synthase 2 increases expression EXP kenpaullone results in increased expression of PTGS2 mRNA CTD PMID:17993264 NCBI chr13:62,163,936...62,172,193
Ensembl chr13:62,163,932...62,172,188 		JBrowse link
G Rgs4 regulator of G-protein signaling 4 decreases expression EXP kenpaullone results in decreased expression of RGS4 mRNA CTD PMID:17993264 NCBI chr13:81,936,775...81,943,103
Ensembl chr13:81,936,775...81,943,068 		JBrowse link
G Sox18 SRY-box transcription factor 18 decreases expression EXP kenpaullone results in decreased expression of SOX18 mRNA CTD PMID:17993264 NCBI chr 3:168,785,488...168,787,290
Ensembl chr 3:168,785,490...168,787,290 		JBrowse link
G Spry1 sprouty RTK signaling antagonist 1 decreases expression EXP kenpaullone results in decreased expression of SPRY1 mRNA CTD PMID:17993264 NCBI chr 2:120,557,256...120,561,917
Ensembl chr 2:120,556,706...120,566,189 		JBrowse link
G Tfr2 transferrin receptor 2 decreases expression ISO kenpaullone results in decreased expression of TFR2 mRNA CTD PMID:25633564 NCBI chr12:19,107,673...19,124,622
Ensembl chr12:19,107,673...19,124,591 		JBrowse link
G Tfrc transferrin receptor increases expression ISO kenpaullone results in increased expression of TFRC mRNA CTD PMID:25633564 NCBI chr11:68,163,413...68,185,257
Ensembl chr11:68,163,413...68,185,257 		JBrowse link
G Tnf tumor necrosis factor decreases expression EXP kenpaullone results in decreased expression of TNF mRNA CTD PMID:17993264 NCBI chr20:3,622,011...3,624,629
Ensembl chr20:3,622,011...3,624,629 		JBrowse link
G Tyr tyrosinase increases expression ISO kenpaullone results in increased expression of TYR mRNA CTD PMID:21071833 NCBI chr 1:141,115,036...141,210,207
Ensembl chr 1:141,115,036...141,210,207 		JBrowse link
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  CHEBI ontology 19932
    role 19904
      application 19741
        pharmaceutical 19579
          drug 19579
            protective agent 18268
              geroprotector 17409
                kenpaullone 46
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  CHEBI ontology 19932
    subatomic particle 19930
      composite particle 19930
        hadron 19930
          baryon 19930
            nucleon 19930
              atomic nucleus 19930
                atom 19930
                  main group element atom 19876
                    p-block element atom 19876
                      carbon group element atom 19816
                        carbon atom 19812
                          organic molecular entity 19812
                            heteroorganic entity 19559
                              organochalcogen compound 19317
                                organooxygen compound 19231
                                  carbon oxoacid 18687
                                    carboxylic acid 18684
                                      carboacyl group 17725
                                        univalent carboacyl group 17725
                                          carbamoyl group 17579
                                            carboxamide 17579
                                              lactam 8391
                                                paullone 47
                                                  kenpaullone 46
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