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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:limonin
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Accession:CHEBI:16226 term browser browse the term
Definition:A hexacyclic triterpenoid that has formula C26H30O8.
Synonyms:exact_synonym: (4aS,6aR,8aR,8bR,9aS,12R,12aS,14aR,14bR)-12-(3-furyl)-6,6,8a,12a-tetramethyldecahydro-3H-oxireno[d]pyrano[4',3':3,3a][2]benzofuro[5,4-f]isochromene-3,8,10(6H,9aH)-trione
 related_synonym: 7,16-Dioxo-7,16-dideoxylimondiol;   Citrolimonin;   Dictamnolactone;   Evodia fruit;   Evodin;   Formula=C26H30O8;   InChI=1S/C26H30O8/c1-22(2)15-9-16(27)24(4)14(25(15)12-31-18(28)10-17(25)33-22)5-7-23(3)19(13-6-8-30-11-13)32-21(29)20-26(23,24)34-20/h6,8,11,14-15,17,19-20H,5,7,9-10,12H2,1-4H3/t14-,15-,17-,19-,20+,23-,24-,25+,26+/m0/s1;   InChIKey=KBDSLGBFQAGHBE-MSGMIQHVSA-N;   Limonoate D-ring-lactone;   Limonoic acid, di-delta-lactone;   Obaculactone;   SMILES=[H][C@]12CC(=O)OC[C@]11[C@@]3([H])CC[C@@]4(C)[C@@H](OC(=O)[C@H]5O[C@@]45[C@]3(C)C(=O)C[C@@]1([H])C(C)(C)O2)c1ccoc1;   limonoic acid 3,19:16,17-dilactone
 alt_id: CHEBI:14509;   CHEBI:14511;   CHEBI:25042;   CHEBI:6467
 xref: AGR:IND44319571;   CAS:1180-71-8;   KEGG:C03514;   KEGG:C16717;   KEGG:D00173;   KNApSAcK:C00003719
 xref_mesh: MESH:C001546
 xref: PMID:19782062;   PMID:21338095;   PMID:22907263;   PMID:22999474;   Wikipedia:Limonin



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limonin term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Aldh1a1 aldehyde dehydrogenase 1 family, member A1 decreases expression
multiple interactions
ISO limonin results in decreased expression of ALDH1A1 mRNA
limonin results in decreased expression of and results in decreased activity of ALDH1A1 protein
CTD PMID:30738134 NCBI chr 1:218,000,470...218,152,962
Ensembl chr 1:218,042,127...218,152,961
JBrowse link
G Bcl2 BCL2, apoptosis regulator multiple interactions ISO coumermycin inhibits the reaction [limonin inhibits the reaction [Arginine results in increased expression of BCL2 protein]]; coumermycin inhibits the reaction [limonin inhibits the reaction [Ceruletide results in increased expression of BCL2 protein]]; limonin inhibits the reaction [Arginine results in increased expression of BCL2 mRNA]; limonin inhibits the reaction [Arginine results in increased expression of BCL2 protein]; limonin inhibits the reaction [Ceruletide results in increased expression of BCL2 mRNA]; limonin inhibits the reaction [Ceruletide results in increased expression of BCL2 protein] CTD PMID:34423886 NCBI chr13:22,689,783...22,853,920 JBrowse link
G Casp3 caspase 3 increases activity ISO limonin results in increased activity of CASP3 protein CTD PMID:31702096 NCBI chr16:45,662,910...45,681,171
Ensembl chr16:45,662,910...45,684,648
JBrowse link
G Casp9 caspase 9 increases activity ISO limonin results in increased activity of CASP9 protein CTD PMID:31702096 NCBI chr 5:154,108,872...154,126,628
Ensembl chr 5:154,109,046...154,126,626
JBrowse link
G Cat catalase multiple interactions ISO limonin inhibits the reaction [Benzo(a)pyrene results in decreased activity of CAT protein] CTD PMID:31702096 NCBI chr 3:89,842,393...89,874,577
Ensembl chr 3:89,842,399...89,874,478
JBrowse link
G Ccl2 C-C motif chemokine ligand 2 multiple interactions ISO coumermycin inhibits the reaction [limonin inhibits the reaction [Arginine results in increased secretion of CCL2 protein]]; coumermycin inhibits the reaction [limonin inhibits the reaction [Ceruletide results in increased secretion of CCL2 protein]]; limonin inhibits the reaction [Arginine results in increased secretion of CCL2 protein]; limonin inhibits the reaction [Ceruletide results in increased secretion of CCL2 protein] CTD PMID:34423886 NCBI chr10:67,005,424...67,007,222
Ensembl chr10:67,005,424...67,007,226
JBrowse link
G Ccn2 cellular communication network factor 2 decreases expression ISO limonin results in decreased expression of CCN2 mRNA CTD PMID:30738134 NCBI chr 1:20,802,199...20,805,315
Ensembl chr 1:20,802,199...20,805,734
JBrowse link
G Ccnd1 cyclin D1 multiple interactions ISO coumermycin inhibits the reaction [limonin inhibits the reaction [Arginine results in increased expression of CCND1 protein]]; coumermycin inhibits the reaction [limonin inhibits the reaction [Ceruletide results in increased expression of CCND1 protein]]; limonin inhibits the reaction [Arginine results in increased expression of CCND1 mRNA]; limonin inhibits the reaction [Arginine results in increased expression of CCND1 protein]; limonin inhibits the reaction [Ceruletide results in increased expression of CCND1 mRNA]; limonin inhibits the reaction [Ceruletide results in increased expression of CCND1 protein] CTD PMID:34423886 NCBI chr 1:200,089,002...200,098,524
Ensembl chr 1:200,089,002...200,098,602
JBrowse link
G Cdh1 cadherin 1 increases expression ISO limonin results in increased expression of CDH1 mRNA; limonin results in increased expression of CDH1 protein CTD PMID:30738134 NCBI chr19:34,492,371...34,561,775
Ensembl chr19:34,492,371...34,561,775
JBrowse link
G Cyp3a2 cytochrome P450, family 3, subfamily a, polypeptide 2 decreases activity ISO limonin results in decreased activity of CYP3A4 protein CTD PMID:22001672 NCBI chr12:9,207,986...9,230,038
Ensembl chr12:9,015,383...9,285,008
JBrowse link
G Ephx2 epoxide hydrolase 2 multiple interactions ISO limonin inhibits the reaction [EPHX2 protein results in increased metabolism of stilbene oxide analog] CTD PMID:2043152 NCBI chr15:40,289,901...40,327,632
Ensembl chr15:40,289,902...40,327,615
JBrowse link
G Gsr glutathione-disulfide reductase multiple interactions ISO limonin inhibits the reaction [Benzo(a)pyrene results in decreased activity of GSR protein] CTD PMID:31702096 NCBI chr16:58,482,209...58,525,256
Ensembl chr16:58,482,505...58,525,661
JBrowse link
G Hmox1 heme oxygenase 1 multiple interactions ISO coumermycin inhibits the reaction [limonin inhibits the reaction [Arginine results in increased expression of HMOX1 protein]]; coumermycin inhibits the reaction [limonin inhibits the reaction [Ceruletide results in increased expression of HMOX1 protein]]; limonin inhibits the reaction [Arginine results in increased expression of HMOX1 protein]; limonin inhibits the reaction [Ceruletide results in increased expression of HMOX1 protein] CTD PMID:34423886 NCBI chr19:13,466,287...13,474,082
Ensembl chr19:13,467,244...13,474,079
JBrowse link
G Il1b interleukin 1 beta multiple interactions ISO coumermycin inhibits the reaction [limonin inhibits the reaction [Arginine results in increased secretion of IL1B protein]]; coumermycin inhibits the reaction [limonin inhibits the reaction [Ceruletide results in increased secretion of IL1B protein]]; limonin inhibits the reaction [Arginine results in increased secretion of IL1B protein]; limonin inhibits the reaction [Benzo(a)pyrene results in increased activity of IL1B protein]; limonin inhibits the reaction [Ceruletide results in increased secretion of IL1B protein] CTD PMID:31702096 PMID:34423886 NCBI chr 3:116,577,005...116,583,386
Ensembl chr 3:116,577,010...116,583,415
JBrowse link
G Il6 interleukin 6 multiple interactions ISO coumermycin inhibits the reaction [limonin inhibits the reaction [Arginine results in increased secretion of IL6 protein]]; coumermycin inhibits the reaction [limonin inhibits the reaction [Ceruletide results in increased secretion of IL6 protein]]; limonin inhibits the reaction [Arginine results in increased secretion of IL6 protein]; limonin inhibits the reaction [Ceruletide results in increased secretion of IL6 protein] CTD PMID:34423886 NCBI chr 4:5,214,602...5,219,178
Ensembl chr 4:5,213,394...5,219,178
JBrowse link
G Jak2 Janus kinase 2 multiple interactions ISO coumermycin inhibits the reaction [limonin inhibits the reaction [Arginine results in increased expression of JAK2 protein]]; coumermycin inhibits the reaction [limonin inhibits the reaction [Ceruletide results in increased expression of JAK2 protein]]; limonin inhibits the reaction [Arginine results in increased expression of JAK2 protein]; limonin inhibits the reaction [Ceruletide results in increased expression of JAK2 protein] CTD PMID:34423886 NCBI chr 1:226,995,334...227,054,381
Ensembl chr 1:226,995,334...227,054,189
JBrowse link
G Nanog Nanog homeobox decreases expression ISO limonin results in decreased expression of NANOG mRNA; limonin results in decreased expression of NANOG protein CTD PMID:30738134 NCBI chr 4:155,943,737...155,951,116
Ensembl chr 4:155,943,737...155,951,116
JBrowse link
G Stat3 signal transducer and activator of transcription 3 multiple interactions ISO coumermycin inhibits the reaction [limonin inhibits the reaction [Arginine results in increased phosphorylation of STAT3 protein]]; coumermycin inhibits the reaction [limonin inhibits the reaction [Ceruletide results in increased phosphorylation of STAT3 protein]]; limonin inhibits the reaction [Arginine results in increased phosphorylation of STAT3 protein]; limonin inhibits the reaction [Ceruletide results in increased phosphorylation of STAT3 protein] CTD PMID:34423886 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 ISO coumermycin inhibits the reaction [limonin inhibits the reaction [Arginine results in increased secretion of TNF protein]]; coumermycin inhibits the reaction [limonin inhibits the reaction [Ceruletide results in increased secretion of TNF protein]]; limonin inhibits the reaction [Arginine results in increased secretion of TNF protein]; limonin inhibits the reaction [Benzo(a)pyrene results in increased activity of TNF protein]; limonin inhibits the reaction [Ceruletide results in increased secretion of TNF protein] CTD PMID:31702096 PMID:34423886 NCBI chr20:3,622,011...3,624,629
Ensembl chr20:3,622,011...3,624,629
JBrowse link
G Vim vimentin decreases expression ISO limonin results in decreased expression of VIM mRNA; limonin results in decreased expression of VIM protein CTD PMID:30738134 NCBI chr17:76,668,701...76,677,186
Ensembl chr17:76,668,647...76,677,187
JBrowse link
G Yap1 Yes1 associated transcriptional regulator affects localization ISO limonin affects the localization of YAP1 protein CTD PMID:30738134 NCBI chr 8:5,095,705...5,166,808
Ensembl chr 8:5,095,722...5,167,010
JBrowse link

Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 20089
    role 20042
      biological role 20011
        inhibitor 18844
          limonin 21
            deoxylimonoic acid 0
            limonin 17-beta-D-glucoside 0
Path 2
Term Annotations click to browse term
  CHEBI ontology 20089
    subatomic particle 20058
      composite particle 20058
        hadron 20088
          baryon 20088
            nucleon 20088
              atomic nucleus 20088
                atom 20058
                  main group element atom 19960
                    p-block element atom 19990
                      carbon group element atom 19916
                        carbon atom 19909
                          organic molecular entity 19909
                            organic group 18988
                              organic divalent group 18950
                                organodiyl group 18974
                                  carbonyl group 18903
                                    carbonyl compound 18925
                                      carboxylic ester 15960
                                        lactone 11302
                                          limonin 21
                                            deoxylimonoic acid 0
                                            limonin 17-beta-D-glucoside 0
paths to the root