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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 4:22,339,829...22,517,642
Ensembl chr 4:22,133,521...22,425,515
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 chr10:549,537...672,235
Ensembl chr10:549,883...672,196
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 1:263,554,426...263,612,556
Ensembl chr 1:263,554,453...263,613,252
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 4:61,813,265...61,830,371
Ensembl chr 4:61,771,970...61,828,657
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 chr17:69,388,337...69,435,160
Ensembl chr17:69,388,335...69,404,341
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 chr20:34,894,419...34,909,265
Ensembl chr20:34,894,419...34,909,265
JBrowse link
G Aurka aurora kinase A increases expression ISO Chlorambucil results in increased expression of AURKA protein CTD PMID:22025197 NCBI chr 3:170,364,177...170,380,278
Ensembl chr 3:170,364,181...170,378,210
JBrowse link
G Aurkb aurora kinase B decreases expression ISO Chlorambucil results in decreased expression of AURKB protein CTD PMID:22025197 NCBI chr10:55,625,860...55,632,399
Ensembl chr10:55,626,741...55,634,991
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 1:101,451,801...101,457,207
Ensembl chr 1:101,451,802...101,457,207
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 1:78,261,491...78,267,802 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 chr13:26,605,426...26,769,374
Ensembl chr13:26,605,426...26,769,374
JBrowse link
G Bik BCL2-interacting killer increases expression ISO Chlorambucil results in increased expression of BIK mRNA CTD PMID:26198647 NCBI chr 7:124,390,924...124,410,449
Ensembl chr 7:124,391,432...124,410,447
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 8:6,014,014...6,036,668
Ensembl chr 8:6,013,207...6,034,142
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 chr10:106,856,097...106,864,419
Ensembl chr10:106,856,097...106,864,413
JBrowse link
G Bmp5 bone morphogenetic protein 5 increases mutagenesis ISO Chlorambucil results in increased mutagenesis of BMP5 gene CTD PMID:10517996 NCBI chr 8:82,669,466...82,950,273
Ensembl chr 8:82,878,941...82,950,273
JBrowse link
G Casp3 caspase 3 increases activity ISO Chlorambucil results in increased activity of CASP3 protein CTD PMID:11675354 NCBI chr16:48,845,011...48,863,249
Ensembl chr16:48,845,012...48,863,204
JBrowse link
G Casp8 caspase 8 increases activity ISO Chlorambucil results in increased activity of CASP8 protein CTD PMID:11675354 NCBI chr 9:65,614,142...65,662,624
Ensembl chr 9:65,614,142...65,662,106
JBrowse link
G Cd59 CD59 molecule decreases lipidation EXP Chlorambucil results in decreased lipidation of CD59 protein CTD PMID:27931811 NCBI chr 3:94,010,481...94,028,660
Ensembl chr 3:94,010,475...94,028,621
JBrowse link
G Cda cytidine deaminase decreases response to substance ISO CDA protein results in decreased susceptibility to Chlorambucil CTD PMID:10830723 NCBI chr 5:156,703,579...156,734,541
Ensembl chr 5:156,703,579...156,734,541
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 chr20:20,576,341...20,591,510
Ensembl chr20:20,576,377...20,591,549
JBrowse link
G Cdkn1a cyclin-dependent kinase inhibitor 1A increases expression ISO Chlorambucil results in increased expression of CDKN1A protein CTD PMID:16039525 NCBI chr20:6,348,422...6,358,864
Ensembl chr20:6,351,458...6,358,864
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 2:21,931,887...21,958,927
Ensembl chr 2:21,931,493...21,962,453
JBrowse link
G Ednrb endothelin receptor type B increases mutagenesis ISO Chlorambucil results in increased mutagenesis of EDNRB gene CTD PMID:10517996 NCBI chr15:88,004,775...88,036,354
Ensembl chr15:88,006,977...88,036,354
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 chr17:826,512...955,703
Ensembl chr17:833,509...955,615
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 5:58,448,060...58,456,416
Ensembl chr 5:58,448,822...58,455,819
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 1:252,589,785...252,624,790
Ensembl chr 1:252,589,785...252,624,790
JBrowse link
G Fbxo30 F-box protein 30 decreases expression ISO Chlorambucil results in decreased expression of FBXO30 mRNA CTD PMID:26198647 NCBI chr 1:5,366,119...5,389,774
Ensembl chr 1:5,366,379...5,388,069
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 8:85,059,051...85,097,471
Ensembl chr 8:85,059,051...85,097,468
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 2:225,827,504...225,847,876
Ensembl chr 2:225,827,504...225,847,874
JBrowse link
G Gsta1 glutathione S-transferase alpha 1 decreases activity
decreases response to substance
multiple interactions
ISO Chlorambucil analog results in decreased activity of GSTA1 protein
GSTA1 protein results in decreased susceptibility to Chlorambucil
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 9:27,366,404...27,381,004
Ensembl chr 9:27,368,272...27,452,902
JBrowse link
G Gsta2 glutathione S-transferase alpha 2 decreases response to substance EXP GSTA3 protein results in decreased susceptibility to Chlorambucil CTD PMID:8044793, PMID:8860835, PMID:10830723, PMID:12872145 NCBI chr 8:85,640,081...85,645,621 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 8:85,553,659...85,564,914
Ensembl chr 8:85,553,734...85,565,179
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 2:210,803,869...210,809,461
Ensembl chr 2:210,803,869...210,809,306
JBrowse link
G Gstp1 glutathione S-transferase pi 1 affects binding
increases metabolic processing
decreases response to substance
affects response to substance
multiple interactions
ISO Chlorambucil binds to GSTP1 protein
GSTP1 protein results in increased metabolism of Chlorambucil
GSTP1 protein results in decreased susceptibility to Chlorambucil
GSTP1 gene affects the susceptibility to Chlorambucil
GSTP1 protein promotes the reaction [ABCC1 protein results in decreased susceptibility to Chlorambucil]
CTD PMID:10900222, PMID:11071881, PMID:18511072 NCBI chr 1:219,291,679...219,294,147
Ensembl chr 1:219,291,679...219,294,147
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 8:48,665,652...48,666,981
Ensembl chr 8:48,665,652...48,666,981
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 chr10:38,963,979...38,969,531
Ensembl chr10:38,963,979...38,969,531
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 8:22,250,518...22,259,868
Ensembl chr 8:22,250,518...22,259,779
JBrowse link
G Lif LIF, interleukin 6 family cytokine increases expression ISO Chlorambucil results in increased expression of LIF mRNA CTD PMID:26198647 NCBI chr14:84,482,652...84,500,574
Ensembl chr14:84,482,674...84,500,642
JBrowse link
G Mdm2 MDM2 proto-oncogene increases expression ISO Chlorambucil results in increased expression of MDM2 mRNA CTD PMID:17476690 NCBI chr 7:60,719,060...60,743,618
Ensembl chr 7:60,719,066...60,743,328
JBrowse link
G Myc MYC proto-oncogene, bHLH transcription factor multiple interactions
affects expression
increases 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 affects the expression of MYC mRNA
Chlorambucil results in increased expression of MYC protein
CTD PMID:8822937 NCBI chr 7:102,586,313...102,591,240
Ensembl chr 7:102,586,313...102,591,240
JBrowse link
G Myo5a myosin VA increases mutagenesis ISO Chlorambucil results in increased mutagenesis of MYO5A gene CTD PMID:10517996 NCBI chr 8:82,038,966...82,156,507
Ensembl chr 8:82,037,977...82,156,617
JBrowse link
G Nfe2l2 nuclear factor, erythroid 2-like 2 multiple interactions
affects response to substance
increases 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 affects the susceptibility to sulforafan] which affects the susceptibility to Chlorambucil
Buthionine Sulfoximine affects the reaction [[NFE2L2 affects the susceptibility to sulforafan] which affects the susceptibility to Chlorambucil]; Buthionine Sulfoximine inhibits the reaction [NFE2L2 protein promotes the reaction [sulforafan results in decreased susceptibility to Chlorambucil]]; NFE2L2 protein promotes the reaction [sulforafan results in decreased susceptibility to Chlorambucil]
NFE2L2 gene mutant form results in increased susceptibility to Chlorambucil
CTD PMID:19303893, PMID:19608619, PMID:20932822 NCBI chr 3:62,497,568...62,525,146
Ensembl chr 3:62,497,571...62,524,996
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:31,786,823...31,799,751
Ensembl chr  X:31,786,194...31,799,560
JBrowse link
G Rad51 RAD51 recombinase increases expression ISO Chlorambucil results in increased expression of RAD51 protein CTD PMID:10473103 NCBI chr 3:110,918,240...110,942,920
Ensembl chr 3:110,918,243...110,942,917
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 chr20:3,875,478...3,885,140
Ensembl chr20:3,875,706...3,881,461
JBrowse link
G Sfn stratifin increases expression ISO Chlorambucil results in increased expression of SFN mRNA CTD PMID:18092340 NCBI chr 5:151,823,422...151,824,937
Ensembl chr 5:151,823,887...151,824,633
JBrowse link
G Tnfrsf10b TNF receptor superfamily member 10b affects expression ISO Chlorambucil affects the expression of TNFRSF10A mRNA CTD PMID:14614459 NCBI chr15:51,433,853...51,464,215 JBrowse link
G Tp53 tumor protein p53 increases expression
multiple interactions
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]
CTD PMID:8822937, PMID:18092340 NCBI chr10:56,186,299...56,198,449
Ensembl chr10:56,187,020...56,198,449
JBrowse link
G Txnrd1 thioredoxin reductase 1 decreases activity EXP Chlorambucil results in decreased activity of TXNRD1 protein CTD PMID:16085187 NCBI chr 7:26,946,124...26,984,400
Ensembl chr 7:26,946,125...26,984,400
JBrowse link
G Tyrp1 tyrosinase-related protein 1 increases mutagenesis ISO Chlorambucil results in increased mutagenesis of TYRP1 gene CTD PMID:10517996 NCBI chr 5:98,387,291...98,406,083
Ensembl chr 5:98,387,291...98,406,083
JBrowse link

Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19816
    role 19764
      biological role 19764
        immunomodulator 13696
          immunosuppressive agent 11941
            chlorambucil 50
Path 2
Term Annotations click to browse term
  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 group 18537
                              organic divalent group 18530
                                organodiyl group 18530
                                  carbonyl group 18436
                                    carbonyl compound 18436
                                      carboxylic acid 18114
                                        monocarboxylic acid 17476
                                          chlorambucil 50
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RGD is funded by grant HL64541 from the National Heart, Lung, and Blood Institute on behalf of the NIH.