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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:levobupivacaine
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Accession:CHEBI:6149 term browser browse the term
Definition:The (S)-(-)-enantiomer of bupivacaine.
Synonyms:exact_synonym: (2S)-1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide
 related_synonym: (-)-bupivacaine;   (S)-1-butyl-2',6'-pipecoloxylidide;   (S)-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)/t16-/m0/s1;   InChIKey=LEBVLXFERQHONN-INIZCTEOSA-N;   L-(-)-1-Butyl-2',6'-pipecoloxylidide;   L-(-)-bupivacaine;   SMILES=CCCCN1CCCC[C@H]1C(=O)Nc1c(C)cccc1C
 xref: CAS:27262-47-1;   DrugBank:DB01002;   Drug_Central:4;   HMDB:HMDB0015137;   KEGG:C07887;   KEGG:D08116
 xref_mesh: MESH:D000077554
 xref: Reaxys:5382240;   Wikipedia:Levobupivacaine
 cyclic_relationship: is_conjugate_base_of CHEBI:77458;   is_enantiomer_of CHEBI:60790


show annotations for term's descendants           Sort by:
levobupivacaine term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Slc25a29 solute carrier family 25 member 29 multiple interactions
decreases activity		 EXP Emulsions inhibits the reaction [Levobupivacaine results in decreased activity of SLC25A29 protein] CTD PMID:35135371 NCBI chr 6:127,742,027...127,752,915
Ensembl chr 6:127,742,033...127,752,940 		JBrowse link
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 1:95,940,001...95,945,407
Ensembl chr 1:95,938,808...95,945,368 		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; HSPA12A protein inhibits the reaction [Bupivacaine results in decreased expression of BCL2 protein]		 CTD PMID:31672611 PMID:34793778 NCBI chr13:22,689,783...22,853,920
Ensembl chr13:22,684,989...22,853,743
Ensembl chr13:22,684,989...22,853,743 		JBrowse link
G Bdnf brain-derived neurotrophic factor multiple interactions
decreases expression		 ISO MIR497 mRNA affects the reaction [Bupivacaine results in decreased expression of BDNF mRNA]; MIR497 mRNA inhibits the reaction [SNHG12 inhibits the reaction [Bupivacaine results in decreased expression of BDNF mRNA]]; NLRX1 protein affects the reaction [MIR497 mRNA affects the reaction [Bupivacaine results in decreased expression of BDNF mRNA]]; SNHG12 inhibits the reaction [Bupivacaine results in decreased expression of BDNF mRNA] CTD PMID:35410500 NCBI chr 3:96,165,042...96,215,621
Ensembl chr 3:96,165,042...96,215,615 		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 chr16:45,662,910...45,681,171
Ensembl chr16:45,662,910...45,684,648 		JBrowse link
G Casp9 caspase 9 decreases expression ISO Bupivacaine results in decreased expression of CASP9 protein CTD PMID:20194319 NCBI chr 5:154,108,872...154,126,628
Ensembl chr 5:154,109,046...154,126,626 		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 chr12:16,806,222...16,846,428
Ensembl chr12:16,806,207...16,846,422 		JBrowse link
G Dnm1l dynamin 1-like decreases expression
multiple interactions		 ISO Bupivacaine results in decreased expression of DNM1L protein
HSPA12A protein inhibits the reaction [Bupivacaine results in decreased expression of DNM1L protein]		 CTD PMID:34793778 NCBI chr11:84,581,216...84,632,382
Ensembl chr11:84,581,216...84,631,482 		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 chr15:44,630,873...44,658,706
Ensembl chr15:44,630,873...44,658,706 		JBrowse link
G H2ax H2A.X variant histone multiple interactions
increases expression		 ISO Glucose promotes the reaction [Bupivacaine results in increased expression of H2AX protein] CTD PMID:31672611 NCBI chr 8:44,671,927...44,673,257
Ensembl chr 8:44,671,786...44,673,239 		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 4:94,368,426...94,397,931
Ensembl chr 4:94,373,342...94,397,883 		JBrowse link
G Hrh1 histamine receptor H 1 affects binding ISO HRH1 protein binds to Bupivacaine CTD PMID:32061592 NCBI chr 4:147,564,781...147,649,353
Ensembl chr 4:147,645,995...147,647,455 		JBrowse link
G Hspa12a heat shock protein family A (Hsp70) member 12A decreases expression
multiple interactions		 ISO Bupivacaine results in decreased expression of HSPA12A protein
HSPA12A protein inhibits the reaction [Bupivacaine results in decreased expression of BCL2 protein]; HSPA12A protein inhibits the reaction [Bupivacaine results in decreased expression of DNM1L protein]; HSPA12A protein inhibits the reaction [Bupivacaine results in decreased expression of MFN1 protein]; HSPA12A protein inhibits the reaction [Bupivacaine results in decreased expression of PINK1 protein]; HSPA12A protein inhibits the reaction [Bupivacaine results in decreased expression of PPARGC1A protein]; HSPA12A protein inhibits the reaction [Bupivacaine results in decreased expression of PRKN protein]; HSPA12A protein inhibits the reaction [Bupivacaine results in decreased expression of SLC2A1 protein]; HSPA12A protein inhibits the reaction [Bupivacaine results in decreased expression of SLC2A4 protein]; HSPA12A protein inhibits the reaction [Bupivacaine results in decreased expression of TOMM20 protein]		 CTD PMID:34793778 NCBI chr 1:257,935,642...258,096,602
Ensembl chr 1:257,935,644...258,096,846 		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 1:182,659,047...182,709,495
Ensembl chr 1:182,659,000...182,709,503 		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 chr11:31,580,951...31,594,116
Ensembl chr11:31,580,742...31,593,901 		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 7:104,429,186...104,473,924
Ensembl chr 7:104,437,934...104,473,175 		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 1:198,291,711...198,624,683
Ensembl chr 1:198,291,766...198,624,669 		JBrowse link
G Mapk1 mitogen activated protein kinase 1 increases phosphorylation
multiple interactions		 ISO Bupivacaine results in increased phosphorylation of MAPK1 protein
Glucose promotes the reaction [Bupivacaine results in increased phosphorylation of MAPK1 protein]		 CTD PMID:34060177 NCBI chr11:83,957,813...84,023,629
Ensembl chr11:83,957,813...84,023,616 		JBrowse link
G Mapk3 mitogen activated protein kinase 3 increases phosphorylation
multiple interactions		 ISO Bupivacaine results in increased phosphorylation of MAPK3 protein
Glucose promotes the reaction [Bupivacaine results in increased phosphorylation of MAPK3 protein]		 CTD PMID:34060177 NCBI chr 1:181,366,646...181,372,863
Ensembl chr 1:181,366,637...181,372,863 		JBrowse link
G Mfn1 mitofusin 1 decreases expression
multiple interactions		 ISO Bupivacaine results in decreased expression of MFN1 protein
HSPA12A protein inhibits the reaction [Bupivacaine results in decreased expression of MFN1 protein]		 CTD PMID:34793778 NCBI chr 2:115,313,380...115,359,651
Ensembl chr 2:115,313,401...115,359,640 		JBrowse link
G Mir497 microRNA 497 multiple interactions
increases expression		 ISO MIR497 mRNA affects the reaction [Bupivacaine results in decreased expression of BDNF mRNA]; MIR497 mRNA inhibits the reaction [SNHG12 inhibits the reaction [Bupivacaine results in decreased expression of BDNF mRNA]]; MIR497 mRNA promotes the reaction [Bupivacaine results in decreased expression of NLRX1 mRNA]; NLRX1 protein affects the reaction [MIR497 mRNA affects the reaction [Bupivacaine results in decreased expression of BDNF mRNA]]; SNHG12 inhibits the reaction [Bupivacaine results in increased expression of MIR497 mRNA] CTD PMID:35410500 NCBI chr10:54,951,514...54,951,582
Ensembl chr10:54,951,505...54,951,584 		JBrowse link
G Myf5 myogenic factor 5 decreases expression EXP Bupivacaine results in decreased expression of MYF5 protein CTD PMID:10434046 NCBI chr 7:42,802,946...42,806,177
Ensembl chr 7:42,802,946...42,806,177 		JBrowse link
G Myod1 myogenic differentiation 1 decreases expression EXP Bupivacaine results in decreased expression of MYOD1 protein CTD PMID:10434046 NCBI chr 1:96,884,864...96,887,574
Ensembl chr 1:96,884,948...96,887,554 		JBrowse link
G Myog myogenin decreases expression EXP Bupivacaine results in decreased expression of MYOG protein CTD PMID:10434046 NCBI chr13:45,745,455...45,748,044
Ensembl chr13:45,745,436...45,748,039 		JBrowse link
G Nlrx1 NLR family member X1 multiple interactions
decreases expression		 ISO MIR497 mRNA promotes the reaction [Bupivacaine results in decreased expression of NLRX1 mRNA]; NLRX1 protein affects the reaction [MIR497 mRNA affects the reaction [Bupivacaine results in decreased expression of BDNF mRNA]]; SNHG12 inhibits the reaction [Bupivacaine results in decreased expression of NLRX1 mRNA] CTD PMID:35410500 NCBI chr 8:44,588,476...44,606,678
Ensembl chr 8:44,590,048...44,606,484 		JBrowse link
G Pink1 PTEN induced kinase 1 decreases expression
multiple interactions		 ISO Bupivacaine results in decreased expression of PINK1 protein
HSPA12A protein inhibits the reaction [Bupivacaine results in decreased expression of PINK1 protein]		 CTD PMID:34793778 NCBI chr 5:150,530,523...150,542,635
Ensembl chr 5:150,530,523...150,542,635 		JBrowse link
G Ppargc1a PPARG coactivator 1 alpha increases expression
decreases expression
multiple interactions		 ISO Bupivacaine results in increased expression of PPARGC1A mRNA
Bupivacaine results in decreased expression of PPARGC1A protein
HSPA12A protein inhibits the reaction [Bupivacaine results in decreased expression of PPARGC1A protein]		 CTD PMID:34793778 NCBI chr14:58,860,752...59,516,525
Ensembl chr14:58,861,144...59,512,656 		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 1:176,832,173...177,163,539
Ensembl chr 1:176,832,226...177,163,536 		JBrowse link
G Prkn parkin RBR E3 ubiquitin protein ligase decreases expression
multiple interactions		 ISO Bupivacaine results in decreased expression of PRKN protein
HSPA12A protein inhibits the reaction [Bupivacaine results in decreased expression of PRKN protein]		 CTD PMID:34793778 NCBI chr 1:48,688,651...49,882,520
Ensembl chr 1:48,690,556...49,882,555 		JBrowse link
G Ptgdr prostaglandin D2 receptor affects expression ISO Bupivacaine affects the expression of PTGDR mRNA CTD PMID:19359520 NCBI chr15:17,360,304...17,367,679
Ensembl chr15:17,360,304...17,367,679 		JBrowse link
G Ptgs1 prostaglandin-endoperoxide synthase 1 increases expression ISO Bupivacaine results in increased expression of PTGS1 mRNA CTD PMID:18165598 NCBI chr 3:19,584,015...19,605,589
Ensembl chr 3:19,584,015...19,605,586 		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 chr13:62,164,080...62,169,770
Ensembl chr13:62,163,932...62,172,188 		JBrowse link
G Slc25a29 solute carrier family 25 member 29 multiple interactions
decreases activity		 EXP Emulsions inhibits the reaction [Bupivacaine results in decreased activity of SLC25A29 protein] CTD PMID:35135371 NCBI chr 6:127,742,027...127,752,915
Ensembl chr 6:127,742,033...127,752,940 		JBrowse link
G Slc2a1 solute carrier family 2 member 1 decreases expression
multiple interactions		 ISO Bupivacaine results in decreased expression of SLC2A1 protein
HSPA12A protein inhibits the reaction [Bupivacaine results in decreased expression of SLC2A1 protein]		 CTD PMID:34793778 NCBI chr 5:132,717,196...132,745,416
Ensembl chr 5:132,717,196...132,745,416 		JBrowse link
G Slc2a4 solute carrier family 2 member 4 multiple interactions
decreases expression		 ISO HSPA12A protein inhibits the reaction [Bupivacaine results in decreased expression of SLC2A4 protein] CTD PMID:34793778 NCBI chr10:54,666,015...54,671,581
Ensembl chr10:54,666,015...54,671,565 		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 chr19:14,010,292...14,055,317
Ensembl chr19:14,010,386...14,050,357 		JBrowse link
G Tomm20 translocase of outer mitochondrial membrane 20 decreases expression
multiple interactions		 ISO Bupivacaine results in decreased expression of TOMM20 protein
HSPA12A protein inhibits the reaction [Bupivacaine results in decreased expression of TOMM20 protein]		 CTD PMID:34793778 NCBI chr19:54,925,197...54,935,188
Ensembl chr19:54,923,402...54,935,198 		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 chr10:57,851,428...57,876,513
Ensembl chr10:57,851,428...57,876,513 		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 7:113,542,992...113,563,762
Ensembl chr 7:113,543,057...113,563,762 		JBrowse link
Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19812
    role 19784
      chemical role 19418
        emulsifier 5161
          surfactant 5161
            amphiphile 38
              levobupivacaine 38
                bupivacaine 38
Path 2
Term Annotations click to browse term
  CHEBI ontology 19812
    subatomic particle 19810
      composite particle 19810
        hadron 19810
          baryon 19810
            nucleon 19810
              atomic nucleus 19810
                atom 19810
                  main group element atom 19755
                    p-block element atom 19755
                      carbon group element atom 19698
                        carbon atom 19693
                          organic molecular entity 19693
                            organic group 18902
                              organic divalent group 18884
                                organodiyl group 18884
                                  carbonyl group 18850
                                    carbonyl compound 18850
                                      carboxylic acid 18564
                                        carboacyl group 17681
                                          univalent carboacyl group 17681
                                            carbamoyl group 17527
                                              carboxamide 17527
                                                monocarboxylic acid amide 15580
                                                  piperidinecarboxamide 48
                                                    1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide 38
                                                      levobupivacaine 38
                                                        bupivacaine 38
paths to the root