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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 1:218,000,470...218,152,962
Ensembl chr 1:218,042,127...218,152,961 		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 chr10:103,072,530...103,081,382
Ensembl chr10:103,073,408...103,081,380 		JBrowse link
G Cat catalase increases activity ISO Butylhydroxybutylnitrosamine results in increased activity of CAT protein CTD PMID:22095756 NCBI chr 3:89,842,393...89,874,577
Ensembl chr 3:89,842,399...89,874,478 		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 1:200,089,002...200,098,524
Ensembl chr 1:200,089,002...200,098,602 		JBrowse link
G Cd44 CD44 molecule increases expression EXP Butylhydroxybutylnitrosamine results in increased expression of CD44 protein CTD PMID:33211169 PMID:35771629 NCBI chr 3:89,155,850...89,244,615
Ensembl chr 3:89,157,058...89,244,620 		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 1:116,714,711...116,837,240 		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 2:195,649,845...195,655,402
Ensembl chr 2:195,649,845...195,655,411 		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 1:246,721,089...246,731,228
Ensembl chr 1:246,721,221...246,731,468 		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 8:44,671,907...44,673,262
Ensembl chr 8:44,671,786...44,673,239 		JBrowse link
G Hgf hepatocyte growth factor increases expression EXP Butylhydroxybutylnitrosamine results in increased expression of HGF protein CTD PMID:35771629 NCBI chr 4:18,673,736...18,745,582
Ensembl chr 4:18,677,101...18,745,409 		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 7:53,903,339...53,907,375
Ensembl chr 7:53,903,337...53,907,375 		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 2:120,004,862...120,009,566
Ensembl chr 2:120,004,862...120,009,566 		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
Ensembl chr10:85,066,802...85,171,799 		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 chr10:85,066,802...85,171,799 		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 7:133,157,475...133,161,166 		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 7:133,124,203...133,131,728 		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 4:175,428,385...175,446,403 		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 1:190,496,319...190,522,983
Ensembl chr 1:190,496,319...190,522,762 		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
NCBI chr MT:5,323...6,867
NCBI chr MT:5,323...6,867
NCBI chr MT:5,323...6,867
NCBI chr MT:5,323...6,867
NCBI chr MT:5,323...6,867
NCBI chr MT:5,323...6,867
NCBI chr MT:5,323...6,867
NCBI chr MT:5,323...6,867
Ensembl chr MT:5,323...6,867 		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 7:93,593,705...93,598,633
Ensembl chr 7:93,593,705...93,598,630 		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 chr19:35,295,633...35,310,528
Ensembl chr19:35,295,573...35,310,557 		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 1:156,297,907...156,372,855
Ensembl chr 1:156,326,259...156,372,855 		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 chr10:47,795,709...47,825,714 		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 1:230,630,443...230,697,070
Ensembl chr 1:230,630,338...230,696,838 		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 chr13:62,163,936...62,172,193
Ensembl chr13:62,163,932...62,172,188 		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 1:202,925,001...202,935,484
Ensembl chr 1:202,924,945...202,935,484 		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 7:133,541,491...133,571,961 		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 chr10:85,811,206...85,863,057
Ensembl chr10:85,811,218...85,863,057 		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 chr20:3,622,011...3,624,629
Ensembl chr20:3,622,011...3,624,629 		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 chr10:83,945,731...83,976,874
Ensembl chr10:83,945,735...83,976,874 		JBrowse link
G Tp53 tumor protein p53 affects activity ISO TRP53 affects the activity of Butylhydroxybutylnitrosamine CTD PMID:10395176 NCBI chr10:54,300,070...54,311,525
Ensembl chr10:54,300,048...54,311,524 		JBrowse link
G Ugt1a1 UDP glucuronosyltransferase family 1 member A1 decreases expression
multiple interactions		 ISO Butylhydroxybutylnitrosamine results in decreased expression of UGT1A7 mRNA
oltipraz inhibits the reaction [Butylhydroxybutylnitrosamine results in decreased expression of UGT1A7 mRNA]		 CTD PMID:15374950 NCBI chr 9:88,801,344...88,808,465
Ensembl chr 9:88,713,184...88,808,465 		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 9:88,747,213...88,808,465
Ensembl chr 9:88,713,184...88,808,465 		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 9:14,955,300...14,970,641
Ensembl chr 9:14,955,300...14,970,641 		JBrowse link
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  CHEBI ontology 19890
    role 19839
      biological role 19858
        aetiopathogenetic role 19213
          carcinogenic agent 18540
            N-butyl-N-(4-hydroxybutyl)nitrosamine 34
              N-butyl-N-(3-carboxypropyl)nitrosamine 0
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  CHEBI ontology 19890
    subatomic particle 19867
      composite particle 19888
        hadron 19888
          baryon 19888
            nucleon 19867
              atomic nucleus 19888
                atom 19888
                  main group element atom 19806
                    p-block element atom 19806
                      chalcogen 19577
                        oxygen atom 19549
                          oxygen molecular entity 19529
                            hydroxides 19334
                              organic hydroxy compound 18963
                                alcohol 15714
                                  primary alcohol 14665
                                    N-butyl-N-(4-hydroxybutyl)nitrosamine 34
                                      N-butyl-N-(3-carboxypropyl)nitrosamine 0
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