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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:bupropion
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Accession:CHEBI:3219 term browser browse the term
Definition:An aromatic ketone that is propiophenone carrying a tert-butylamino group at position 2 and a chloro substituent at position 3 on the phenyl ring.
Synonyms:exact_synonym: 2-(tert-butylamino)-1-(3-chlorophenyl)propan-1-one
 related_synonym: Formula=C13H18ClNO;   InChI=1S/C13H18ClNO/c1-9(15-13(2,3)4)12(16)10-6-5-7-11(14)8-10/h5-9,15H,1-4H3;   InChIKey=SNPPWIUOZRMYNY-UHFFFAOYSA-N;   SMILES=CC(NC(C)(C)C)C(=O)c1cccc(Cl)c1
 xref: Beilstein:2101062;   CAS:34841-39-9;   CAS:34911-55-2;   DrugBank:DB01156;   Drug_Central:435;   HMDB:HMDB0001510;   KEGG:C06860;   KEGG:D07591;   LINCS:LSM-1267
 xref_mesh: MESH:D016642
 xref: MetaCyc:CPD-3481;   PMID:12826985;   PMID:15876900;   Reaxys:2101062;   Wikipedia:Bupropion


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bupropion term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Abcb6 ATP binding cassette subfamily B member 6 multiple interactions
decreases metabolic processing
ISO [ABCB6 gene mutant form results in decreased expression of CYP2B10 mRNA] inhibits the reaction [CYP2B10 protein results in increased metabolism of Bupropion]; [ABCB6 gene mutant form results in decreased expression of CYP2B10 protein] inhibits the reaction [CYP2B10 protein results in increased metabolism of Bupropion]
ABCB6 gene mutant form results in decreased metabolism of Bupropion
CTD PMID:25623066 NCBI chr 9:82,373,950...82,382,228
Ensembl chr 9:82,373,946...82,382,272
JBrowse link
G Casp3 caspase 3 multiple interactions ISO Bupropion results in increased cleavage of and results in increased activity of CASP3 protein CTD PMID:21354251 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 Bupropion results in increased activity of CASP8 protein CTD PMID:21354251 NCBI chr 9:65,614,142...65,662,624
Ensembl chr 9:65,614,142...65,662,106
JBrowse link
G Casp9 caspase 9 increases activity ISO Bupropion results in increased activity of CASP9 protein CTD PMID:21354251 NCBI chr 5:160,356,211...160,373,774
Ensembl chr 5:160,355,833...160,373,778
JBrowse link
G Cat catalase decreases activity ISO Bupropion results in decreased activity of CAT protein CTD PMID:16085363 NCBI chr 3:93,379,872...93,412,058
Ensembl chr 3:93,379,874...93,412,058
JBrowse link
G Cd74 CD74 molecule affects expression ISO Bupropion affects the expression of CD74 mRNA CTD PMID:25811541 NCBI chr18:56,071,420...56,080,851
Ensembl chr18:56,071,478...56,080,849
JBrowse link
G Cyp2b1 cytochrome P450, family 2, subfamily b, polypeptide 1 multiple interactions
increases metabolic processing
ISO
EXP
[ABCB6 gene mutant form results in decreased expression of CYP2B10 mRNA] inhibits the reaction [CYP2B10 protein results in increased metabolism of Bupropion]; [ABCB6 gene mutant form results in decreased expression of CYP2B10 protein] inhibits the reaction [CYP2B10 protein results in increased metabolism of Bupropion]
[CYP2B1 protein results in increased metabolism of Bupropion] which results in increased chemical synthesis of hydroxybupropion
CTD PMID:25623066, PMID:28438436 NCBI chr 7:99,142,431...99,183,540
Ensembl chr 7:99,142,450...99,181,783
JBrowse link
G Cyp2b3 cytochrome P450, family 2, subfamily b, polypeptide 3 affects metabolic processing
increases hydroxylation
multiple interactions
increases metabolic processing
increases hydrolysis
ISO CYP2B6 protein affects the metabolism of Bupropion
CYP2B6 protein results in increased hydroxylation of Bupropion
2-(4'-methoxybenzenesulfonyl)-2,3,4,9-tetrahydro-1H-pyrido(3,4-b)indole-3-carboxylic acid amide inhibits the reaction [CYP2B6 protein results in increased hydroxylation of Bupropion]; [5-bromotryptamine analog results in decreased activity of CYP2B6 protein] which results in decreased metabolism of Bupropion; [5-chlorotryptamine analog results in decreased activity of CYP2B6 protein] which results in decreased metabolism of Bupropion; [5-fluoro-alpha-methyltryptamine analog results in decreased activity of CYP2B6 protein] which results in decreased metabolism of Bupropion; [5-fluorotryptamine analog results in decreased activity of CYP2B6 protein] which results in decreased metabolism of Bupropion; [5-methoxy-N,N-diisopropyltryptamine analog results in decreased activity of CYP2B6 protein] which results in decreased metabolism of Bupropion; [5-methyltryptamine analog results in decreased activity of CYP2B6 protein] which results in decreased metabolism of Bupropion; [7-methyltryptamine analog results in decreased activity of CYP2B6 protein] which results in decreased metabolism of Bupropion; [CYP2B6 protein results in increased metabolism of Bupropion] which results in increased chemical synthesis of hydroxybupropion; [CYP2B6 protein results in increased metabolism of Bupropion] which results in increased chemical synthesis of radafaxine; [efavirenz results in decreased activity of CYP2B6 protein] which results in decreased metabolism of Bupropion; [indopan analog results in decreased activity of CYP2B6 protein] which results in decreased metabolism of Bupropion; [indopan results in decreased activity of CYP2B6 protein] which results in decreased metabolism of Bupropion; [Methoxydimethyltryptamines analog results in decreased activity of CYP2B6 protein] which results in decreased metabolism of Bupropion; [N,N-diallyl-5-methoxytryptamine results in decreased activity of CYP2B6 protein] which results in decreased metabolism of Bupropion; [N,N-diisopropyltryptamine analog results in decreased activity of CYP2B6 protein] which results in decreased metabolism of Bupropion; [Sertraline results in decreased activity of CYP2B6 protein] which results in decreased metabolism of Bupropion; [Tryptamines analog results in decreased activity of CYP2B6 protein] which results in decreased metabolism of Bupropion; Camphor inhibits the reaction [CYP2B6 protein results in increased hydrolysis of Bupropion]; citral inhibits the reaction [CYP2B6 protein results in increased hydrolysis of Bupropion]; Clorgyline inhibits the reaction [CYP2B6 protein results in increased hydroxylation of Bupropion]; cyhalothrin inhibits the reaction [CYP2B6 protein results in increased hydroxylation of Bupropion]; decamethrin inhibits the reaction [CYP2B6 protein results in increased hydroxylation of Bupropion]; Eucalyptol inhibits the reaction [CYP2B6 protein results in increased hydrolysis of Bupropion]; Fenitrothion inhibits the reaction [CYP2B6 protein results in increased hydroxylation of Bupropion]; fenvalerate inhibits the reaction [CYP2B6 protein results in increased hydroxylation of Bupropion]; geraniol inhibits the reaction [CYP2B6 protein results in increased hydrolysis of Bupropion]; isoborneol inhibits the reaction [CYP2B6 protein results in increased hydrolysis of Bupropion]; Menthol inhibits the reaction [CYP2B6 protein results in increased hydrolysis of Bupropion]; notopterol inhibits the reaction [[CYP2B6 protein results in increased metabolism of Bupropion] which results in increased chemical synthesis of hydroxybupropion]; notopterol inhibits the reaction [CYP2B6 protein results in increased metabolism of Bupropion]; Pargyline inhibits the reaction [CYP2B6 protein results in increased hydroxylation of Bupropion]; Paroxetine inhibits the reaction [CYP2B6 protein results in increased metabolism of Bupropion]; perillaldehyde inhibits the reaction [CYP2B6 protein results in increased hydrolysis of Bupropion]; Phenelzine inhibits the reaction [CYP2B6 protein results in increased hydroxylation of Bupropion]; Selegiline inhibits the reaction [CYP2B6 protein results in increased hydroxylation of Bupropion]; sibutramine inhibits the reaction [CYP2B6 protein results in increased hydroxylation of Bupropion]; Thiotepa inhibits the reaction [CYP2B6 protein results in increased hydrolysis of Bupropion]; Thiotepa inhibits the reaction [CYP2B6 protein results in increased hydroxylation of Bupropion]; Ticlopidine inhibits the reaction [CYP2B6 protein results in increased metabolism of Bupropion]; Ticrynafen inhibits the reaction [CYP2B6 protein results in increased metabolism of Bupropion]; Tranylcypromine inhibits the reaction [CYP2B6 protein results in increased metabolism of Bupropion]
CTD PMID:15155557, PMID:15626586, PMID:15769884, PMID:16124035, PMID:17565714, PMID:18611395, PMID:19135037, PMID:21915887, PMID:22634058, PMID:23777987, PMID:23850985, PMID:25084468, PMID:25656918, PMID:26599973, PMID:27387538, PMID:27590069, PMID:28119166, PMID:28762043, PMID:29445054, PMID:32198085 NCBI chr 1:83,163,103...83,236,615
Ensembl chr 1:83,163,079...83,236,615
JBrowse link
G Cyp2c6v1 cytochrome P450, family 2, subfamily C, polypeptide 6, variant 1 multiple interactions ISO CYP2C19 gene polymorphism affects the metabolism of and affects the abundance of Bupropion CTD PMID:25187485 NCBI chr 1:147,713,879...147,814,410
Ensembl chr 1:147,713,892...147,888,007
JBrowse link
G Dbh dopamine beta-hydroxylase increases response to substance ISO DBH protein results in increased susceptibility to Bupropion CTD PMID:15148402 NCBI chr 3:5,709,236...5,731,895
Ensembl chr 3:5,709,236...5,731,898
JBrowse link
G Eif2s1 eukaryotic translation initiation factor 2 subunit alpha increases phosphorylation ISO Bupropion results in increased phosphorylation of EIF2S1 protein CTD PMID:21354251 NCBI chr 6:102,048,372...102,073,041
Ensembl chr 6:102,048,372...102,073,041
JBrowse link
G Fos Fos proto-oncogene, AP-1 transcription factor subunit multiple interactions ISO [Bupropion co-treated with SLC6A3 protein] results in increased expression of FOS protein; Bupropion inhibits the reaction [[Dopamine co-treated with SLC6A3 protein] results in increased expression of FOS mRNA]; Bupropion inhibits the reaction [[Dopamine co-treated with SLC6A3 protein] results in increased expression of FOS protein] CTD PMID:12112414 NCBI chr 6:109,300,433...109,303,299
Ensembl chr 6:109,300,433...109,303,299
JBrowse link
G Hmgcs1 3-hydroxy-3-methylglutaryl-CoA synthase 1 increases expression ISO Bupropion results in increased expression of HMGCS1 mRNA CTD PMID:16324787 NCBI chr 2:52,427,351...52,445,082
Ensembl chr 2:52,431,601...52,445,055
JBrowse link
G Hspa5 heat shock protein family A (Hsp70) member 5 increases expression ISO Bupropion results in increased expression of HSPA5 protein CTD PMID:21354251 NCBI chr 3:13,838,304...13,842,763
Ensembl chr 3:13,838,304...13,842,762
JBrowse link
G Htr2a 5-hydroxytryptamine receptor 2A multiple interactions EXP Bupropion inhibits the reaction [Adrenocorticotropic Hormone affects the expression of HTR2A mRNA] CTD PMID:18239281 NCBI chr15:56,666,152...56,732,469
Ensembl chr15:56,666,012...56,735,382
JBrowse link
G LOC100364500 RT1 class I, locus CE11-like affects expression ISO Bupropion affects the expression of HLA-A mRNA CTD PMID:25811541 NCBI chr20:2,704,153...2,707,111
Ensembl chr20:2,704,148...2,707,120
JBrowse link
G Mapk14 mitogen activated protein kinase 14 multiple interactions ISO Bupropion results in increased phosphorylation of and results in increased activity of MAPK14 protein CTD PMID:21354251 NCBI chr20:5,933,290...5,995,137
Ensembl chr20:5,933,303...5,995,137
JBrowse link
G Mapk8 mitogen-activated protein kinase 8 multiple interactions ISO Bupropion results in increased phosphorylation of and results in increased activity of MAPK8 protein CTD PMID:21354251 NCBI chr16:9,620,854...9,709,342
Ensembl chr16:9,625,177...9,709,347
JBrowse link
G Mr1 major histocompatibility complex, class I-related affects expression ISO Bupropion affects the expression of MR1 mRNA CTD PMID:25811541 NCBI chr13:72,771,992...72,789,861
Ensembl chr13:72,771,984...72,789,841
JBrowse link
G Nr1i3 nuclear receptor subfamily 1, group I, member 3 increases hydroxylation ISO NR1I3 mRNA results in increased hydroxylation of Bupropion CTD PMID:32428594 NCBI chr13:89,585,072...89,591,278
Ensembl chr13:89,586,283...89,591,277
JBrowse link
G Scd stearoyl-CoA desaturase increases expression ISO Bupropion results in increased expression of SCD mRNA CTD PMID:16324787 NCBI chr 1:264,159,966...264,173,061
Ensembl chr 1:264,160,129...264,172,729
JBrowse link
G Sec24d SEC24 homolog D, COPII coat complex component increases response to substance ISO SEC24D protein results in increased susceptibility to Bupropion CTD PMID:27555326 NCBI chr 2:227,455,704...227,562,801
Ensembl chr 2:227,455,722...227,562,319
JBrowse link
G Slc22a2 solute carrier family 22 member 2 multiple interactions ISO Bupropion inhibits the reaction [SLC22A2 protein results in increased uptake of 4-(4-dimethylaminostyryl)-1-methylpyridinium] CTD PMID:21599003 NCBI chr 1:48,318,025...48,360,219
Ensembl chr 1:48,317,995...48,360,261
JBrowse link
G Slc6a3 solute carrier family 6 member 3 multiple interactions
affects response to substance
increases expression
ISO [Bupropion co-treated with SLC6A3 protein] results in increased expression of FOS protein; [SLC6A3 protein polymorphism affects the susceptibility to Bupropion] which affects the uptake of Dopamine; Bupropion inhibits the reaction [[Dopamine co-treated with SLC6A3 protein] results in increased expression of FOS mRNA]; Bupropion inhibits the reaction [[Dopamine co-treated with SLC6A3 protein] results in increased expression of FOS protein]; Bupropion inhibits the reaction [SLC6A3 protein mutant form results in decreased import of Dopamine]; Bupropion inhibits the reaction [SLC6A3 protein results in increased uptake of Dopamine]; Bupropion promotes the reaction [SLC6A3 protein results in increased import of Dopamine]
Bupropion results in increased expression of SLC6A3 protein
CTD PMID:12112414, PMID:27555326, PMID:31009648 NCBI chr 1:32,323,011...32,363,983
Ensembl chr 1:32,321,580...32,363,983
JBrowse link
G Slc6a4 solute carrier family 6 member 4 affects response to substance ISO SLC6A4 polymorphism affects the susceptibility to Bupropion CTD PMID:21658141 NCBI chr10:63,153,656...63,188,377
Ensembl chr10:63,153,651...63,176,463
JBrowse link
G Sod1 superoxide dismutase 1 increases expression EXP Bupropion results in increased expression of SOD1 mRNA CTD PMID:10721683 NCBI chr11:30,363,282...30,368,858
Ensembl chr11:30,363,280...30,368,862
JBrowse link
G Tnfrsf10b TNF receptor superfamily member 10b increases expression ISO Bupropion results in increased expression of TNFRSF10A mRNA CTD PMID:21354251 NCBI chr15:51,433,853...51,464,215 JBrowse link
G Xbp1 X-box binding protein 1 decreases splicing ISO Bupropion results in decreased splicing of XBP1 mRNA CTD PMID:21354251 NCBI chr14:85,753,736...85,758,820
Ensembl chr14:85,753,760...85,758,145
JBrowse link

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  CHEBI ontology 19816
    role 19764
      biological role 19764
        xenobiotic 18413
          bupropion 28
            (R)-bupropion 0
            (S)-bupropion 0
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
                    main group molecular entity 19702
                      s-block molecular entity 19461
                        hydrogen molecular entity 19452
                          hydrides 18707
                            inorganic hydride 17430
                              pnictogen hydride 17402
                                nitrogen hydride 17243
                                  azane 16960
                                    ammonia 16959
                                      organic amino compound 16958
                                        secondary amino compound 6532
                                          bupropion 28
                                            (R)-bupropion 0
                                            (S)-bupropion 0
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RGD is funded by grant HL64541 from the National Heart, Lung, and Blood Institute on behalf of the NIH.