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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:chlorambucil
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Accession:CHEBI:28830 term browser browse the term
Definition:A monocarboxylic acid that is butanoic acid substituted at position 4 by a 4-[bis(2-chloroethyl)amino]phenyl group. A chemotherapy drug that can be used in combination with the antibody obinutuzumab for the treatment of chronic lymphocytic leukemia.
Synonyms:exact_synonym: 4-{4-[bis(2-chloroethyl)amino]phenyl}butanoic acid
 related_synonym: 4-(p-bis(beta-chloroethyl)aminophenyl)butyric acid;   4-[p-[bis(2-chloroethyl)amino]phenyl]butyric acid;   Ambochlorin;   Formula=C14H19Cl2NO2;   InChI=1S/C14H19Cl2NO2/c15-8-10-17(11-9-16)13-6-4-12(5-7-13)2-1-3-14(18)19/h4-7H,1-3,8-11H2,(H,18,19);   InChIKey=JCKYGMPEJWAADB-UHFFFAOYSA-N;   Leukeran;   N,N-di-2-chloroethyl-gamma-p-aminophenylbutyric acid;   SMILES=OC(=O)CCCc1ccc(cc1)N(CCCl)CCCl;   chloraminophen;   gamma-[p-di(2-chloroethyl)aminophenyl]butyric acid;   phenylbutyric acid nitrogen mustard
 alt_id: CHEBI:25817;   CHEBI:3601;   CHEBI:48770
 xref: Beilstein:999011;   CAS:305-03-3;   DrugBank:DB00291;   Drug_Central:588;   KEGG:D00266;   LINCS:LSM-2645
 xref_mesh: MESH:D002699
 xref: PDBeChem:CBL;   PMID:22025197;   PMID:22978684;   PMID:23233721;   PMID:23295789;   PMID:23521128;   PMID:23665800;   PMID:23667729;   PMID:23683018;   PMID:23725434;   PMID:23822827;   PMID:24098639;   PMID:24147900;   PMID:24223689;   Reaxys:999011;   Wikipedia:Chlorambucil


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chlorambucil 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 Chlorambucil results in increased expression of ABCB1 protein CTD PMID:15239124 NCBI chr 4:25,357,467...25,529,941
Ensembl chr 4:25,158,362...25,442,709 		JBrowse link
G Abcc1 ATP binding cassette subfamily C member 1 affects export
decreases response to substance
increases response to substance
multiple interactions		 ISO ABCC1 protein affects the export of Chlorambucil analog
ABCC1 protein results in decreased susceptibility to Chlorambucil
ABCC1 protein results in increased susceptibility to Chlorambucil
buthionine sulfoximine ethyl ester promotes the reaction [ABCC1 protein results in increased susceptibility to Chlorambucil]; GSTP1 protein promotes the reaction [ABCC1 protein results in decreased susceptibility to Chlorambucil]		 CTD PMID:10900222 PMID:11115505 PMID:12504668 PMID:14569069 NCBI chr10:528,961...655,179
Ensembl chr10:531,812...655,114 		JBrowse link
G Abcc2 ATP binding cassette subfamily C member 2 affects export
multiple interactions		 ISO ABCC2 protein affects the export of Chlorambucil analog
ABCC2 protein promotes the reaction [GSTA1 protein results in decreased susceptibility to Chlorambucil]		 CTD PMID:14569069 NCBI chr 1:242,664,657...242,723,239
Ensembl chr 1:242,664,657...242,723,238 		JBrowse link
G Akr1b10 aldo-keto reductase family 1 member B10 decreases expression ISO Chlorambucil results in decreased expression of AKR1B10 mRNA CTD PMID:26198647 NCBI chr 4:63,038,459...63,060,336
Ensembl chr 4:63,040,169...63,053,852 		JBrowse link
G Akr1c2 aldo-keto reductase family 1, member C2 decreases expression ISO Chlorambucil results in decreased expression of AKR1C2 mRNA CTD PMID:26198647 NCBI chr17:65,759,778...65,808,013
Ensembl chr17:65,759,788...65,775,764 		JBrowse link
G Asf1a anti-silencing function 1A histone chaperone decreases expression ISO Chlorambucil results in decreased expression of ASF1A mRNA CTD PMID:26198647 NCBI chr20:32,893,962...32,908,808
Ensembl chr20:32,893,573...32,908,808 		JBrowse link
G Aurka aurora kinase A increases expression ISO Chlorambucil results in increased expression of AURKA protein CTD PMID:22025197 NCBI chr 3:161,128,309...161,144,524
Ensembl chr 3:161,128,313...161,144,390 		JBrowse link
G Aurkb aurora kinase B decreases expression ISO Chlorambucil results in decreased expression of AURKB protein CTD PMID:22025197 NCBI chr10:53,744,290...53,750,831
Ensembl chr10:53,745,142...53,750,837 		JBrowse link
G Bax BCL2 associated X, apoptosis regulator increases expression ISO Chlorambucil results in increased expression of BAX protein CTD PMID:11699414 NCBI chr 1:95,940,001...95,945,407
Ensembl chr 1:95,938,808...95,945,368 		JBrowse link
G Bbc3 Bcl-2 binding component 3 increases expression ISO Chlorambucil results in increased expression of BBC3 mRNA CTD PMID:17476690 NCBI chr 1:77,013,281...77,022,509
Ensembl chr 1:77,014,543...77,022,509 		JBrowse link
G Bcl2 BCL2, apoptosis regulator decreases expression
multiple interactions		 ISO Chlorambucil results in decreased expression of BCL2 mRNA; Chlorambucil results in decreased expression of BCL2 protein
IL4 protein inhibits the reaction [Chlorambucil results in decreased expression of BCL2 protein]		 CTD PMID:8822937 PMID:11699414 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 Bik BCL2-interacting killer increases expression ISO Chlorambucil results in increased expression of BIK mRNA CTD PMID:26198647 NCBI chr 7:114,672,277...114,691,296
Ensembl chr 7:114,672,277...114,691,296 		JBrowse link
G Birc2 baculoviral IAP repeat-containing 2 decreases response to substance ISO BIRC2 protein results in decreased susceptibility to Chlorambucil CTD PMID:10815900 NCBI chr 8:4,968,856...4,989,325
Ensembl chr 8:4,968,842...4,988,732 		JBrowse link
G Birc5 baculoviral IAP repeat-containing 5 affects expression
decreases expression		 ISO Chlorambucil affects the expression of BIRC5 mRNA
Chlorambucil results in decreased expression of BIRC5 protein		 CTD PMID:17476690 PMID:22025197 NCBI chr10:103,072,530...103,081,382
Ensembl chr10:103,073,408...103,081,380 		JBrowse link
G Bmp5 bone morphogenetic protein 5 increases mutagenesis ISO Chlorambucil results in increased mutagenesis of BMP5 gene CTD PMID:10517996 NCBI chr 8:76,517,164...76,639,925
Ensembl chr 8:76,517,164...76,639,925 		JBrowse link
G Casp3 caspase 3 increases activity ISO Chlorambucil results in increased activity of CASP3 protein CTD PMID:11675354 NCBI chr16:45,662,910...45,681,171
Ensembl chr16:45,662,910...45,684,648 		JBrowse link
G Casp8 caspase 8 increases activity ISO Chlorambucil results in increased activity of CASP8 protein CTD PMID:11675354 NCBI chr 9:60,263,863...60,312,542
Ensembl chr 9:60,264,075...60,312,542 		JBrowse link
G Ccl2 C-C motif chemokine ligand 2 multiple interactions ISO Chlorambucil promotes the reaction [lipopolysaccharide, E coli O55-B5 results in increased secretion of CCL2 protein] CTD PMID:36416909 NCBI chr10:67,005,424...67,007,222
Ensembl chr10:67,005,424...67,007,226 		JBrowse link
G Cd59b CD59b molecule decreases lipidation EXP Chlorambucil results in decreased lipidation of CD59 protein CTD PMID:27931811 NCBI chr 3:90,459,085...90,477,571
Ensembl chr 3:90,459,162...90,478,847 		JBrowse link
G Cda cytidine deaminase decreases response to substance ISO CDA protein results in decreased susceptibility to Chlorambucil CTD PMID:10830723 NCBI chr 5:150,556,615...150,583,231
Ensembl chr 5:150,556,615...150,583,231 		JBrowse link
G Cdk1 cyclin-dependent kinase 1 multiple interactions ISO Chlorambucil analog results in increased phosphorylation of and results in decreased activity of CDK1 protein CTD PMID:16861886 NCBI chr20:19,266,226...19,281,417
Ensembl chr20:19,266,248...19,281,408 		JBrowse link
G Cdkn1a cyclin-dependent kinase inhibitor 1A increases expression ISO Chlorambucil results in increased expression of CDKN1A protein CTD PMID:16039525 NCBI chr20:7,149,177...7,159,727
Ensembl chr20:7,149,217...7,159,585 		JBrowse link
G Dhfr dihydrofolate reductase decreases response to substance ISO DHFR protein polymorphism results in decreased susceptibility to Chlorambucil CTD PMID:12872145 NCBI chr 2:23,585,876...23,611,199
Ensembl chr 2:23,586,031...23,613,713 		JBrowse link
G Ednrb endothelin receptor type B increases mutagenesis ISO Chlorambucil results in increased mutagenesis of EDNRB gene CTD PMID:10517996 NCBI chr15:80,640,839...80,672,115
Ensembl chr15:80,643,043...80,672,115 		JBrowse link
G Fancc FA complementation group C increases response to substance ISO FANCC protein results in increased susceptibility to Chlorambucil CTD PMID:16243825 NCBI chr17:1,680,660...1,822,610
Ensembl chr17:1,681,324...1,829,376 		JBrowse link
G Fancg FA complementation group G increases response to substance ISO FANCG protein results in increased susceptibility to Chlorambucil CTD PMID:16243825 NCBI chr 5:57,230,287...57,240,067
Ensembl chr 5:57,231,685...57,240,029 		JBrowse link
G Fas Fas cell surface death receptor increases expression ISO Chlorambucil results in increased expression of FAS mRNA CTD PMID:11675354 PMID:17476690 NCBI chr 1:231,798,963...231,832,591
Ensembl chr 1:231,798,960...231,832,591 		JBrowse link
G Fbxo30 F-box protein 30 decreases expression ISO Chlorambucil results in decreased expression of FBXO30 mRNA CTD PMID:26198647 NCBI chr 1:5,655,341...5,671,558
Ensembl chr 1:5,655,339...5,672,441 		JBrowse link
G Gclc glutamate-cysteine ligase, catalytic subunit multiple interactions ISO [GCLC protein co-treated with GCLM protein] results in decreased susceptibility to Chlorambucil CTD PMID:10900222 NCBI chr 8:78,629,899...78,668,547
Ensembl chr 8:78,630,127...78,668,544 		JBrowse link
G Gclm glutamate cysteine ligase, modifier subunit multiple interactions ISO [GCLC protein co-treated with GCLM protein] results in decreased susceptibility to Chlorambucil CTD PMID:10900222 NCBI chr 2:210,347,482...210,367,537
Ensembl chr 2:210,347,482...210,367,535 		JBrowse link
G Gsta1 glutathione S-transferase alpha 1 decreases activity
multiple interactions
decreases response to substance		 ISO Chlorambucil analog results in decreased activity of GSTA1 protein
ABCC2 protein promotes the reaction [GSTA1 protein results in decreased susceptibility to Chlorambucil]; GSTA1 protein affects the metabolism of [Chlorambucil co-treated with Glutathione]		 CTD PMID:11115505 PMID:14569069 NCBI chr 9:23,703,476...23,720,121
Ensembl chr 9:23,703,477...23,720,121 		JBrowse link
G Gsta3 glutathione S-transferase alpha 3 decreases response to substance EXP GSTA3 protein results in decreased susceptibility to Chlorambucil CTD PMID:8044793 PMID:8860835 PMID:10830723 PMID:12872145 NCBI chr 9:23,658,574...23,684,240
Ensembl chr 9:23,658,574...23,684,240 		JBrowse link
G Gsta5 glutathione S-transferase alpha 5 decreases response to substance EXP GSTA5 protein results in decreased susceptibility to Chlorambucil CTD PMID:12076520 NCBI chr 8:79,105,561...79,117,472
Ensembl chr 8:79,105,661...79,117,472 		JBrowse link
G Gstm1 glutathione S-transferase mu 1 decreases response to substance ISO GSTM1 protein results in decreased susceptibility to Chlorambucil CTD PMID:15044619 PMID:20067466 NCBI chr 2:195,649,845...195,655,402
Ensembl chr 2:195,649,845...195,655,411 		JBrowse link
G Gstp1 glutathione S-transferase pi 1 affects binding
multiple interactions
affects response to substance
decreases response to substance
increases metabolic processing		 ISO Chlorambucil binds to GSTP1 protein
GSTP1 protein promotes the reaction [ABCC1 protein results in decreased susceptibility to Chlorambucil]
GSTP1 gene affects the susceptibility to Chlorambucil
GSTP1 protein results in decreased susceptibility to Chlorambucil
GSTP1 protein results in increased metabolism of Chlorambucil		 CTD PMID:10900222 PMID:11071881 PMID:18511072 NCBI chr 1:201,337,762...201,340,230
Ensembl chr 1:201,321,672...201,340,226 		JBrowse link
G H2ax H2A.X variant histone increases phosphorylation ISO Chlorambucil analog results in increased phosphorylation of H2AX protein; Chlorambucil results in increased phosphorylation of H2AX protein CTD PMID:16861886 PMID:32482060 NCBI chr 8:44,671,907...44,673,262
Ensembl chr 8:44,671,786...44,673,239 		JBrowse link
G Il4 interleukin 4 multiple interactions ISO IL4 protein inhibits the reaction [[Theophylline co-treated with Chlorambucil] results in increased expression of MYC protein]; IL4 protein inhibits the reaction [[Theophylline co-treated with Chlorambucil] results in increased expression of TP53]; IL4 protein inhibits the reaction [Chlorambucil results in decreased expression of BCL2 protein] CTD PMID:8822937 NCBI chr10:37,771,203...37,776,750
Ensembl chr10:37,771,203...37,776,750 		JBrowse link
G Keap1 Kelch-like ECH-associated protein 1 multiple interactions ISO [KEAP1 gene mutant form results in increased activity of NFE2L2] which results in decreased susceptibility to Chlorambucil; Buthionine Sulfoximine inhibits the reaction [[KEAP1 gene mutant form results in increased activity of NFE2L2] which results in decreased susceptibility to Chlorambucil] CTD PMID:19608619 NCBI chr 8:19,768,375...19,777,862
Ensembl chr 8:19,768,375...19,777,862 		JBrowse link
G Lif LIF, interleukin 6 family cytokine increases expression ISO Chlorambucil results in increased expression of LIF mRNA CTD PMID:26198647 NCBI chr14:79,131,049...79,140,486
Ensembl chr14:79,134,574...79,140,482 		JBrowse link
G Mdm2 MDM2 proto-oncogene increases expression ISO Chlorambucil results in increased expression of MDM2 mRNA CTD PMID:17476690 NCBI chr 7:53,290,660...53,315,205
Ensembl chr 7:53,290,664...53,314,915 		JBrowse link
G Myc MYC proto-oncogene, bHLH transcription factor multiple interactions
increases expression
affects expression		 ISO [Theophylline co-treated with Chlorambucil] results in increased expression of MYC protein; IL4 protein inhibits the reaction [[Theophylline co-treated with Chlorambucil] results in increased expression of MYC protein]
Chlorambucil results in increased expression of MYC protein
Chlorambucil affects the expression of MYC mRNA		 CTD PMID:8822937 NCBI chr 7:93,593,705...93,598,633
Ensembl chr 7:93,593,705...93,598,630 		JBrowse link
G Myo5a myosin VA increases mutagenesis ISO Chlorambucil results in increased mutagenesis of MYO5A gene CTD PMID:10517996 NCBI chr 8:75,811,985...75,980,049
Ensembl chr 8:75,812,412...75,975,918 		JBrowse link
G Nfe2l2 NFE2 like bZIP transcription factor 2 multiple interactions
increases response to substance
affects response to substance		 ISO [KEAP1 gene mutant form results in increased activity of NFE2L2] which results in decreased susceptibility to Chlorambucil; Buthionine Sulfoximine inhibits the reaction [[KEAP1 gene mutant form results in increased activity of NFE2L2] which results in decreased susceptibility to Chlorambucil]
NFE2L2 gene mutant form results in increased susceptibility to Chlorambucil
Buthionine Sulfoximine affects the reaction [[NFE2L2 affects the susceptibility to sulforaphane] which affects the susceptibility to Chlorambucil]; Buthionine Sulfoximine inhibits the reaction [NFE2L2 protein promotes the reaction [sulforaphane results in decreased susceptibility to Chlorambucil]]; NFE2L2 protein promotes the reaction [sulforaphane results in decreased susceptibility to Chlorambucil]		 CTD PMID:19303893 PMID:19608619 PMID:20932822 NCBI chr 3:60,594,239...60,621,712
Ensembl chr 3:60,594,242...60,621,737 		JBrowse link
G Pdk4 pyruvate dehydrogenase kinase 4 affects expression ISO Chlorambucil affects the expression of PDK4 mRNA CTD PMID:32870474 NCBI chr 4:33,591,796...33,601,798
Ensembl chr 4:33,589,799...33,601,850 		JBrowse link
G Piga phosphatidylinositol glycan anchor biosynthesis, class A increases mutagenesis
multiple interactions		 EXP Chlorambucil results in increased mutagenesis of PIGA
Chlorambucil results in increased mutagenesis of and results in decreased activity of PIGA protein		 CTD PMID:22923490 PMID:27931811 NCBI chr  X:30,043,033...30,055,861
Ensembl chr  X:30,042,343...30,055,804 		JBrowse link
G Rad51 RAD51 recombinase increases expression ISO Chlorambucil results in increased expression of RAD51 protein CTD PMID:10473103 NCBI chr 3:106,099,753...106,125,038
Ensembl chr 3:106,100,381...106,125,035 		JBrowse link
G RT1-Ha RT1 class II, locus Ha affects expression ISO Chlorambucil affects the expression of HLA-DPA1 mRNA CTD PMID:25811541 NCBI chr20:4,760,631...4,770,662
Ensembl chr20:4,760,118...4,770,244 		JBrowse link
G Sfn stratifin increases expression ISO Chlorambucil results in increased expression of SFN mRNA CTD PMID:18092340 NCBI chr 5:145,826,722...145,827,994
Ensembl chr 5:145,826,201...145,831,314 		JBrowse link
G Tnfrsf10b TNF receptor superfamily member 10b affects expression ISO Chlorambucil affects the expression of TNFRSF10A mRNA CTD PMID:14614459 NCBI chr15:44,840,386...44,868,318
Ensembl chr15:44,840,386...44,867,467 		JBrowse link
G Tp53 tumor protein p53 increases expression
multiple interactions
affects activity		 ISO Chlorambucil results in increased expression of TP53; Chlorambucil results in increased expression of TP53 protein
[Theophylline co-treated with Chlorambucil] results in increased expression of TP53; IL4 protein inhibits the reaction [[Theophylline co-treated with Chlorambucil] results in increased expression of TP53]
Chlorambucil affects the activity of TP53 protein		 CTD PMID:8822937 PMID:18092340 PMID:35435491 NCBI chr10:54,300,070...54,311,525
Ensembl chr10:54,300,048...54,311,524 		JBrowse link
G Txnrd1 thioredoxin reductase 1 decreases activity EXP Chlorambucil results in decreased activity of TXNRD1 protein CTD PMID:16085187 NCBI chr 7:20,830,042...20,914,990
Ensembl chr 7:20,830,045...20,907,863 		JBrowse link
G Tyrp1 tyrosinase-related protein 1 increases mutagenesis ISO Chlorambucil results in increased mutagenesis of TYRP1 gene CTD PMID:10517996 NCBI chr 5:95,280,982...95,299,516
Ensembl chr 5:95,280,982...95,299,516 		JBrowse link
Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19911
    role 19854
      biological role 19852
        immunomodulator 15081
          immunosuppressive agent 13924
            chlorambucil 52
Path 2
Term Annotations click to browse term
  CHEBI ontology 19911
    subatomic particle 19909
      composite particle 19909
        hadron 19880
          baryon 19880
            nucleon 19909
              atomic nucleus 19880
                atom 19909
                  main group element atom 19849
                    main group molecular entity 19849
                      s-block molecular entity 19681
                        hydrogen molecular entity 19662
                          hydrides 19167
                            inorganic hydride 18182
                              pnictogen hydride 18172
                                nitrogen hydride 18085
                                  azane 17866
                                    ammonia 17865
                                      organic amino compound 17888
                                        tertiary amino compound 10155
                                          chlorambucil 52
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