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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:1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide
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Accession:CHEBI:77431 term browser browse the term
Definition:A piperidinecarboxamide obtained by formal condensation of the carboxy group of N-butylpipecolic acid with the amino group of 2,6-dimethylaniline.
Synonyms:related_synonym: DL-Bupivacaine;   Formula=C18H28N2O;   InChI=1S/C18H28N2O/c1-4-5-12-20-13-7-6-11-16(20)18(21)19-17-14(2)9-8-10-15(17)3/h8-10,16H,4-7,11-13H2,1-3H3,(H,19,21);   InChIKey=LEBVLXFERQHONN-UHFFFAOYSA-N;   Marcaine;   SMILES=CCCCN1CCCCC1C(=O)Nc1c(C)cccc1C;   bupivacaina;   bupivacainum
 xref: CAS:38396-39-3;   KEGG:C07529;   KEGG:D07552
 cyclic_relationship: is_conjugate_base_of CHEBI:77457


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bupivacaine term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Bax BCL2 associated X, apoptosis regulator increases expression
multiple interactions
ISO Bupivacaine results in increased expression of BAX protein
8-dibenzothiophen-4-yl-2-morpholin-4-yl-chromen-4-one promotes the reaction [[Glucose co-treated with Bupivacaine] results in increased expression of BAX protein]; [Glucose co-treated with Bupivacaine] results in increased expression of BAX protein
CTD PMID:31672611 NCBI chr 1:101,451,801...101,457,207
Ensembl chr 1:101,451,802...101,457,207
JBrowse link
G Bcl2 BCL2, apoptosis regulator decreases expression
multiple interactions
ISO Bupivacaine results in decreased expression of BCL2 protein
8-dibenzothiophen-4-yl-2-morpholin-4-yl-chromen-4-one promotes the reaction [[Glucose co-treated with Bupivacaine] results in decreased expression of BCL2 protein]; [Glucose co-treated with Bupivacaine] results in decreased expression of BCL2 protein
CTD PMID:31672611 NCBI chr13:26,605,426...26,769,374
Ensembl chr13:26,605,426...26,769,374
JBrowse link
G Casp3 caspase 3 decreases expression
increases activity
ISO
EXP
Bupivacaine results in decreased expression of CASP3 protein
Bupivacaine results in increased activity of CASP3 protein
CTD PMID:16109997, PMID:20194319 NCBI chr16:48,845,011...48,863,249
Ensembl chr16:48,845,012...48,863,204
JBrowse link
G Casp9 caspase 9 decreases expression ISO Bupivacaine results in decreased expression of CASP9 protein CTD PMID:20194319 NCBI chr 5:160,356,211...160,373,774
Ensembl chr 5:160,355,833...160,373,778
JBrowse link
G Cyp3a9 cytochrome P450, family 3, subfamily a, polypeptide 9 multiple interactions EXP [Bupivacaine co-treated with Tetrodotoxin co-treated with Dexamethasone] results in decreased expression of CYP3A9 mRNA CTD PMID:22341215 NCBI chr12:19,074,288...19,114,491
Ensembl chr12:19,074,583...19,114,399
JBrowse link
G Entpd4 ectonucleoside triphosphate diphosphohydrolase 4 multiple interactions EXP [Bupivacaine co-treated with Tetrodotoxin co-treated with Dexamethasone] results in decreased expression of ENTPD4 mRNA CTD PMID:22341215 NCBI chr15:51,222,954...51,250,787
Ensembl chr15:51,222,954...51,250,787
JBrowse link
G Hpgds hematopoietic prostaglandin D synthase increases expression ISO Bupivacaine results in increased expression of HPGDS mRNA; Bupivacaine results in increased expression of HPGDS protein CTD PMID:19359520 NCBI chr 4:95,945,356...95,970,666
Ensembl chr 4:95,946,025...95,970,666
JBrowse link
G Hrh1 histamine receptor H 1 affects binding ISO HRH1 protein binds to Bupivacaine CTD PMID:32061592 NCBI chr 4:146,374,596...146,458,148
Ensembl chr 4:146,455,332...146,457,074
JBrowse link
G Itgam integrin subunit alpha M increases expression
multiple interactions
ISO Bupivacaine results in increased expression of ITGAM mRNA
4-benzhydryloxy-1-(3-(1H-tetrazol-5-yl-)-propyl)piperidine inhibits the reaction [Bupivacaine results in increased expression of ITGAM mRNA]
CTD PMID:19359520 NCBI chr 1:199,495,312...199,545,738
Ensembl chr 1:199,495,298...199,623,960
JBrowse link
G Kcne1 potassium voltage-gated channel subfamily E regulatory subunit 1 multiple interactions ISO Bupivacaine results in decreased activity of [KCNQ1 protein binds to KCNE1 protein]; KCNE1 protein inhibits the reaction [KCNQ1 protein mutant form results in increased susceptibility to Bupivacaine] CTD PMID:16931984 NCBI chr11:32,498,260...32,511,202
Ensembl chr11:32,498,261...32,508,420
JBrowse link
G Kcnk9 potassium two pore domain channel subfamily K member 9 multiple interactions ISO Bupivacaine inhibits the reaction [KCNK9 protein results in increased transport of Potassium] CTD PMID:11249964 NCBI chr 7:113,894,918...113,938,397
Ensembl chr 7:113,903,557...113,937,941
JBrowse link
G Kcnq1 potassium voltage-gated channel subfamily Q member 1 multiple interactions
decreases activity
increases response to substance
ISO Bupivacaine results in decreased activity of [KCNQ1 protein binds to KCNE1 protein]; KCNE1 protein inhibits the reaction [KCNQ1 protein mutant form results in increased susceptibility to Bupivacaine]
Bupivacaine results in decreased activity of KCNQ1 protein
CTD PMID:16931984 NCBI chr 1:216,293,087...216,630,339
Ensembl chr 1:216,293,087...216,630,339
JBrowse link
G Myf5 myogenic factor 5 decreases expression EXP Bupivacaine results in decreased expression of MYF5 protein CTD PMID:10434046 NCBI chr 7:49,729,533...49,732,974
Ensembl chr 7:49,729,533...49,732,764
JBrowse link
G Myod1 myogenic differentiation 1 decreases expression EXP Bupivacaine results in decreased expression of MYOD1 protein CTD PMID:10434046 NCBI chr 1:102,396,538...102,399,248
Ensembl chr 1:102,396,538...102,399,248
JBrowse link
G Myog myogenin decreases expression EXP Bupivacaine results in decreased expression of MYOG protein CTD PMID:10434046 NCBI chr13:51,126,459...51,129,048
Ensembl chr13:51,126,459...51,129,048
JBrowse link
G Prkcb protein kinase C, beta multiple interactions EXP [Bupivacaine co-treated with Tetrodotoxin co-treated with Dexamethasone] results in decreased expression of PRKCB mRNA CTD PMID:22341215 NCBI chr 1:192,233,569...192,575,339
Ensembl chr 1:192,233,910...192,574,831
JBrowse link
G Ptgdr prostaglandin D2 receptor affects expression ISO Bupivacaine affects the expression of PTGDR mRNA CTD PMID:19359520 NCBI chr15:19,195,606...19,196,508 JBrowse link
G Ptgs1 prostaglandin-endoperoxide synthase 1 increases expression ISO Bupivacaine results in increased expression of PTGS1 mRNA CTD PMID:18165598 NCBI chr 3:15,560,685...15,582,339
Ensembl chr 3:15,560,712...15,582,344
JBrowse link
G Ptgs2 prostaglandin-endoperoxide synthase 2 increases expression
multiple interactions
ISO Bupivacaine results in increased expression of PTGS2 mRNA
[Bupivacaine results in increased expression of PTGS2] which results in increased abundance of Dinoprostone
CTD PMID:18165598 NCBI chr13:67,351,230...67,356,920
Ensembl chr13:67,351,087...67,359,335
JBrowse link
G Slc6a2 solute carrier family 6 member 2 multiple interactions ISO Bupivacaine inhibits the reaction [[Desipramine results in decreased activity of SLC6A2 protein] which results in decreased abundance of Norepinephrine] CTD PMID:16725121 NCBI chr19:15,391,682...15,431,274
Ensembl chr19:15,391,581...15,431,274
JBrowse link
G Trpv1 transient receptor potential cation channel, subfamily V, member 1 increases activity
multiple interactions
EXP Bupivacaine results in increased activity of TRPV1 protein
Bupivacaine affects the reaction [Capsaicin results in increased activity of TRPV1 protein]
CTD PMID:15854744, PMID:18172555 NCBI chr10:59,799,123...59,824,208
Ensembl chr10:59,799,123...59,824,679
JBrowse link
G Xrcc6 X-ray repair cross complementing 6 increases expression
multiple interactions
ISO Bupivacaine results in increased expression of XRCC6 protein
8-dibenzothiophen-4-yl-2-morpholin-4-yl-chromen-4-one inhibits the reaction [[Glucose co-treated with Bupivacaine] results in increased expression of XRCC6 protein]; [Glucose co-treated with Bupivacaine] results in increased expression of XRCC6 protein; Glucose inhibits the reaction [Bupivacaine results in increased expression of XRCC6 protein]
CTD PMID:31672611 NCBI chr 7:123,259,881...123,280,613
Ensembl chr 7:123,259,761...123,280,612
JBrowse link

Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19785
    role 19732
      application 19391
        refrigerant 17418
          ammonia 16939
            organic amino compound 16938
              tertiary amino compound 8629
                1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide 22
                  dextrobupivacaine + 22
                  levobupivacaine + 22
Path 2
Term Annotations click to browse term
  CHEBI ontology 19785
    subatomic particle 19782
      composite particle 19782
        hadron 19782
          baryon 19782
            nucleon 19782
              atomic nucleus 19782
                atom 19782
                  main group element atom 19670
                    p-block element atom 19670
                      carbon group element atom 19572
                        carbon atom 19561
                          organic molecular entity 19561
                            organic group 18493
                              organic divalent group 18486
                                organodiyl group 18486
                                  carbonyl group 18389
                                    carbonyl compound 18389
                                      carboxylic acid 18060
                                        carboacyl group 17346
                                          univalent carboacyl group 17346
                                            carbamoyl group 17132
                                              carboxamide 17132
                                                monocarboxylic acid amide 14551
                                                  piperidinecarboxamide 30
                                                    1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide 22
                                                      dextrobupivacaine + 22
                                                      levobupivacaine + 22
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