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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:N-butyl-N-(4-hydroxybutyl)nitrosamine
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Accession:CHEBI:91275 term browser browse the term
Definition:A nitrosamine that has butyl and 4-hydroxybutyl substituents. In mice, it causes high-grade, invasive cancers in the urinary bladder, but not in any other tissues.
Synonyms:exact_synonym: N-butyl-N-(4-hydroxybutyl)nitrous amide
 related_synonym: 4-(butylnitrosamino)-1-butanol;   4-(butylnitrosoamino)butanol;   4-hydroxybutylbutylnitrosamine;   BBN;   Formula=C8H18N2O2;   InChI=1S/C8H18N2O2/c1-2-3-6-10(9-12)7-4-5-8-11/h11H,2-8H2,1H3;   InChIKey=DIKPQFXYECAYPC-UHFFFAOYSA-N;   N-butyl-(4-hydroxybutyl)nitrosamine;   N-nitroso-N-butyl-(4-hydroxybutyl)amine;   N-nitroso-N-butyl-N-(4-carboxypropyl)amine;   N-nitrosobutylbutanolamine;   SMILES=C(O)CCCN(CCCC)N=O;   butyl(4-hydroxybutyl)nitrosamine;   butylbutanolnitrosamine;   butylhydroxybutylnitrosamine
 xref: CAS:3817-11-6
 xref_mesh: MESH:D002085
 xref: PMID:16886626;   PMID:22095756;   PMID:22155125;   PMID:26782701;   PMID:8065076;   Reaxys:2080574



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N-butyl-N-(4-hydroxybutyl)nitrosamine term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Aldh1a1 aldehyde dehydrogenase 1 family, member A1 increases expression EXP Butylhydroxybutylnitrosamine results in increased expression of ALDH1A1 protein CTD PMID:33211169 PMID:35771629 NCBI chr 1:227,426,939...227,579,497
Ensembl chr 1:227,427,070...227,579,500
JBrowse link
G Birc5 baculoviral IAP repeat-containing 5 multiple interactions EXP [Butylhydroxybutylnitrosamine co-treated with Propolis analog] results in increased expression of BIRC5 mRNA CTD PMID:26111810 NCBI chr10:103,567,369...103,580,069
Ensembl chr10:103,572,080...103,582,155
JBrowse link
G Cat catalase increases activity ISO Butylhydroxybutylnitrosamine results in increased activity of CAT protein CTD PMID:22095756 NCBI chr 3:110,297,340...110,329,526
Ensembl chr 3:110,297,342...110,329,526
JBrowse link
G Ccnd1 cyclin D1 multiple interactions EXP [Butylhydroxybutylnitrosamine co-treated with Propolis analog] results in increased expression of CCND1 mRNA CTD PMID:26111810 NCBI chr 1:209,518,288...209,527,986
Ensembl chr 1:209,518,288...209,527,810
JBrowse link
G Cd44 CD44 molecule increases expression EXP Butylhydroxybutylnitrosamine results in increased expression of CD44 protein CTD PMID:33211169 PMID:35771629 NCBI chr 3:109,610,824...109,699,776
Ensembl chr 3:109,612,054...109,699,424
JBrowse link
G Chrna7 cholinergic receptor nicotinic alpha 7 subunit multiple interactions EXP [Nicotine co-treated with Butylhydroxybutylnitrosamine] results in increased expression of CHRNA7 protein CTD PMID:29501575 NCBI chr 1:116,711,559...116,837,269
Ensembl chr 1:126,123,425...126,446,858
JBrowse link
G Gstm1 glutathione S-transferase mu 1 decreases expression ISO Butylhydroxybutylnitrosamine results in decreased expression of GSTM1 protein CTD PMID:24998975 NCBI chr 2:198,338,005...198,346,007
Ensembl chr 2:198,338,008...198,343,569
JBrowse link
G Gsto1 glutathione S-transferase omega 1 increases expression ISO Butylhydroxybutylnitrosamine results in increased expression of GSTO1 protein CTD PMID:24998975 NCBI chr 1:256,662,377...256,672,515
Ensembl chr 1:256,662,531...256,676,167
JBrowse link
G H2ax H2A.X variant histone increases expression EXP Butylhydroxybutylnitrosamine results in increased expression of H2AX protein CTD PMID:26338220 PMID:35771629 NCBI chr 8:53,568,718...53,570,072
Ensembl chr 8:53,568,281...53,573,079
JBrowse link
G Hgf hepatocyte growth factor increases expression EXP Butylhydroxybutylnitrosamine results in increased expression of HGF protein CTD PMID:35771629 NCBI chr 4:19,628,902...19,700,467
Ensembl chr 4:19,632,267...19,700,851
JBrowse link
G Ifng interferon gamma multiple interactions EXP 2-Acetylaminofluorene inhibits the reaction [[Diethylnitrosamine co-treated with Methylnitrosourea co-treated with Butylhydroxybutylnitrosamine co-treated with diisopropanolnitrosamine co-treated with 1,2-Dimethylhydrazine] results in decreased expression of IFNG protein]; [Diethylnitrosamine co-treated with Methylnitrosourea co-treated with Butylhydroxybutylnitrosamine co-treated with diisopropanolnitrosamine co-treated with 1,2-Dimethylhydrazine] results in decreased expression of IFNG protein CTD PMID:14736494 NCBI chr 7:55,789,180...55,793,216
Ensembl chr 7:55,761,736...55,793,216
JBrowse link
G Il2 interleukin 2 multiple interactions EXP [Diethylnitrosamine co-treated with Methylnitrosourea co-treated with Butylhydroxybutylnitrosamine co-treated with diisopropanolnitrosamine co-treated with 1,2-Dimethylhydrazine] results in decreased expression of IL2 protein CTD PMID:14736494 NCBI chr 2:121,932,968...121,937,672
Ensembl chr 2:121,932,968...121,937,672
JBrowse link
G Krt14 keratin 14 increases expression EXP Butylhydroxybutylnitrosamine results in increased expression of KRT14 protein CTD PMID:33211169 NCBI chr10:85,137,786...85,142,054 JBrowse link
G Krt15 keratin 15 increases expression ISO Butylhydroxybutylnitrosamine results in increased expression of KRT15 protein CTD PMID:24998975 NCBI chr10:85,066,797...85,070,614
Ensembl chr10:85,567,202...85,571,142
JBrowse link
G Krt18 keratin 18 decreases expression ISO Butylhydroxybutylnitrosamine results in decreased expression of KRT18 protein CTD PMID:24998975 NCBI chr 7:133,157,486...133,161,162
Ensembl chr 7:135,035,982...135,039,848
Ensembl chr10:135,035,982...135,039,848
JBrowse link
G Krt8 keratin 8 decreases expression ISO Butylhydroxybutylnitrosamine results in decreased expression of KRT8 protein CTD PMID:24998975 NCBI chr 7:133,124,203...133,131,656
Ensembl chr 7:135,002,894...135,010,403
JBrowse link
G Ldhb lactate dehydrogenase B decreases expression ISO Butylhydroxybutylnitrosamine results in decreased expression of LDHB protein CTD PMID:24998975 NCBI chr 4:175,428,382...175,446,403
Ensembl chr 4:177,159,392...177,177,408
JBrowse link
G Mki67 marker of proliferation Ki-67 multiple interactions EXP [Nicotine co-treated with Butylhydroxybutylnitrosamine] results in increased expression of MKI67 protein; Hexamethonium inhibits the reaction [[Nicotine co-treated with Butylhydroxybutylnitrosamine] results in increased expression of MKI67 protein]; methyllycaconitine inhibits the reaction [[Nicotine co-treated with Butylhydroxybutylnitrosamine] results in increased expression of MKI67 protein] CTD PMID:29501575 NCBI chr 1:199,926,150...199,952,847
Ensembl chr 1:199,926,150...199,952,593
JBrowse link
G Mt-co1 mitochondrially encoded cytochrome c oxidase I decreases expression ISO Butylhydroxybutylnitrosamine results in decreased expression of COX1 protein CTD PMID:22095756 NCBI chr MT:5,323...6,867
Ensembl chr MT:5,309...6,853
JBrowse link
G Myc MYC proto-oncogene, bHLH transcription factor multiple interactions
increases expression
ISO
EXP
Butylhydroxybutylnitrosamine results in increased expression of and results in increased localization of MYC protein; Niacinamide inhibits the reaction [Butylhydroxybutylnitrosamine results in increased expression of and results in increased localization of MYC protein]
Butylhydroxybutylnitrosamine results in increased expression of MYC mRNA
CTD PMID:22028816 PMID:35771629 NCBI chr 7:95,483,105...95,488,031
Ensembl chr 7:95,483,105...95,488,028
JBrowse link
G Nqo1 NAD(P)H quinone dehydrogenase 1 decreases expression ISO Butylhydroxybutylnitrosamine results in decreased expression of NQO1 protein CTD PMID:24998975 NCBI chr19:52,205,374...52,220,267
Ensembl chr19:52,205,314...52,220,260
JBrowse link
G Numa1 nuclear mitotic apparatus protein 1 multiple interactions EXP 3,3'-diindolylmethane inhibits the reaction [[Butylhydroxybutylnitrosamine co-treated with Cacodylic Acid] results in increased expression of NUMA1 protein]; [Butylhydroxybutylnitrosamine co-treated with Cacodylic Acid] results in increased expression of NUMA1 protein; lupeol inhibits the reaction [[Butylhydroxybutylnitrosamine co-treated with Cacodylic Acid] results in increased expression of NUMA1 protein] CTD PMID:26251508 NCBI chr 1:165,709,893...165,784,848
Ensembl chr 1:165,709,905...165,784,848
JBrowse link
G Pmp22 peripheral myelin protein 22 multiple interactions ISO Butylhydroxybutylnitrosamine results in decreased expression of and results in decreased localization of PMP22 protein; Niacinamide inhibits the reaction [Butylhydroxybutylnitrosamine results in decreased expression of and results in decreased localization of PMP22 protein] CTD PMID:22028816 NCBI chr10:47,795,709...47,825,715
Ensembl chr10:48,297,437...48,324,940
JBrowse link
G Pten phosphatase and tensin homolog multiple interactions EXP 3,3'-diindolylmethane inhibits the reaction [[Butylhydroxybutylnitrosamine co-treated with Cacodylic Acid] results in decreased expression of PTEN protein]; [Butylhydroxybutylnitrosamine co-treated with Cacodylic Acid] results in decreased expression of PTEN protein; lupeol inhibits the reaction [[Butylhydroxybutylnitrosamine co-treated with Cacodylic Acid] results in decreased expression of PTEN protein] CTD PMID:26251508 NCBI chr 1:240,043,707...240,110,330
Ensembl chr 1:240,043,707...240,110,330
JBrowse link
G Ptgs2 prostaglandin-endoperoxide synthase 2 multiple interactions EXP 3,3'-diindolylmethane inhibits the reaction [[Butylhydroxybutylnitrosamine co-treated with Cacodylic Acid] results in increased expression of PTGS2 protein]; [Butylhydroxybutylnitrosamine co-treated with Cacodylic Acid] results in increased expression of PTGS2 protein; lupeol inhibits the reaction [[Butylhydroxybutylnitrosamine co-treated with Cacodylic Acid] results in increased expression of PTGS2 protein] CTD PMID:26251508 NCBI chr13:64,714,063...64,722,320
Ensembl chr13:64,713,619...64,722,320
JBrowse link
G Rela RELA proto-oncogene, NF-kB subunit multiple interactions EXP 3,3'-diindolylmethane inhibits the reaction [[Butylhydroxybutylnitrosamine co-treated with Cacodylic Acid] results in increased phosphorylation of RELA protein]; [Butylhydroxybutylnitrosamine co-treated with Cacodylic Acid] results in increased phosphorylation of RELA protein; lupeol inhibits the reaction [[Butylhydroxybutylnitrosamine co-treated with Cacodylic Acid] results in increased phosphorylation of RELA protein] CTD PMID:26251508 NCBI chr 1:212,354,336...212,364,815
Ensembl chr 1:212,333,035...212,364,817
JBrowse link
G Sp1 Sp1 transcription factor increases expression ISO Butylhydroxybutylnitrosamine results in increased expression of SP1 protein CTD PMID:24998975 NCBI chr 7:133,541,302...133,571,961
Ensembl chr 7:135,420,050...135,450,513
JBrowse link
G Stat3 signal transducer and activator of transcription 3 multiple interactions
increases expression
EXP [Nicotine co-treated with Butylhydroxybutylnitrosamine] results in increased expression of STAT3 protein modified form; Hexamethonium inhibits the reaction [[Nicotine co-treated with Butylhydroxybutylnitrosamine] results in increased expression of STAT3 protein modified form]; methyllycaconitine inhibits the reaction [[Nicotine co-treated with Butylhydroxybutylnitrosamine] results in increased expression of STAT3 protein modified form]
Butylhydroxybutylnitrosamine results in increased expression of STAT3 mRNA
CTD PMID:29501575 PMID:35771629 NCBI chr10:86,311,528...86,363,513
Ensembl chr10:86,311,535...86,363,359
JBrowse link
G Tnf tumor necrosis factor multiple interactions EXP 3,3'-diindolylmethane inhibits the reaction [[Butylhydroxybutylnitrosamine co-treated with Cacodylic Acid] results in increased expression of TNF protein]; [Butylhydroxybutylnitrosamine co-treated with Cacodylic Acid] results in increased expression of TNF protein; lupeol inhibits the reaction [[Butylhydroxybutylnitrosamine co-treated with Cacodylic Acid] results in increased expression of TNF protein] CTD PMID:26251508 NCBI chr20:3,626,685...3,629,303
Ensembl chr20:3,626,532...3,629,303
JBrowse link
G Top2a DNA topoisomerase II alpha multiple interactions EXP [Butylhydroxybutylnitrosamine co-treated with Propolis analog] results in increased expression of TOP2A mRNA CTD PMID:26111810 NCBI chr10:84,441,954...84,473,093
Ensembl chr10:84,441,954...84,473,366
JBrowse link
G Tp53 tumor protein p53 affects activity ISO TRP53 affects the activity of Butylhydroxybutylnitrosamine CTD PMID:10395176 NCBI chr10:54,798,871...54,810,300
Ensembl chr10:54,798,851...54,810,299
JBrowse link
G Ugt1a1 UDP glucuronosyltransferase family 1 member A1 multiple interactions
decreases expression
ISO oltipraz inhibits the reaction [Butylhydroxybutylnitrosamine results in decreased expression of UGT1A7 mRNA] CTD PMID:15374950 NCBI chr 9:96,249,143...96,256,264
Ensembl chr 9:96,144,786...96,256,264
JBrowse link
G Ugt1a6 UDP glucuronosyltransferase family 1 member A6 multiple interactions
decreases expression
ISO oltipraz inhibits the reaction [Butylhydroxybutylnitrosamine results in decreased expression of UGT1A6 mRNA] CTD PMID:15374950 NCBI chr 9:96,195,018...96,256,264
Ensembl chr 9:96,144,786...96,256,264
JBrowse link
G Vegfa vascular endothelial growth factor A increases expression EXP Butylhydroxybutylnitrosamine results in increased expression of VEGFA protein CTD PMID:24888239 NCBI chr 9:22,452,854...22,468,194
Ensembl chr 9:22,439,392...22,468,194
JBrowse link

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  CHEBI ontology 20862
    role 20820
      biological role 20818
        aetiopathogenetic role 19855
          carcinogenic agent 18936
            N-butyl-N-(4-hydroxybutyl)nitrosamine 34
              N-butyl-N-(3-carboxypropyl)nitrosamine 0
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  CHEBI ontology 20862
    subatomic particle 20860
      composite particle 20860
        hadron 20860
          baryon 20860
            nucleon 20860
              atomic nucleus 20860
                atom 20860
                  main group element atom 20781
                    p-block element atom 20781
                      chalcogen 20491
                        oxygen atom 20457
                          oxygen molecular entity 20457
                            hydroxides 20230
                              organic hydroxy compound 19765
                                alcohol 16148
                                  primary alcohol 15242
                                    N-butyl-N-(4-hydroxybutyl)nitrosamine 34
                                      N-butyl-N-(3-carboxypropyl)nitrosamine 0
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