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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:loliolide
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Accession:CHEBI:69774 term browser browse the term
Definition:A benzofuran that has formula C11H16O3.
Synonyms:related_synonym: (6S,7aR)-6-hydroxy-4,4,7a-trimethyl-6,7-dihydro-5H-1-benzofuran-2-one;   Formula=C11H16O3;   InChI=1S/C11H16O3/c1-10(2)5-7(12)6-11(3)8(10)4-9(13)14-11/h4,7,12H,5-6H2,1-3H3/t7-,11+/m0/s1;   InChIKey=XEVQXKKKAVVSMW-WRWORJQWSA-N;   SMILES=CC1(C)C[C@H](O)C[C@@]2(C)OC(=O)C=C12
 xref: CAS:5989-02-6
 xref_mesh: MESH:C030425
 xref: PMID:21634415


show annotations for term's descendants           Sort by:
loliolide term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Acaca acetyl-CoA carboxylase alpha decreases expression
multiple interactions		 ISO loliolide results in decreased expression of ACACA protein
[loliolide co-treated with pinoresinol] results in decreased expression of ACACA protein		 CTD PMID:31610126 NCBI chr10:69,014,261...69,276,453
Ensembl chr10:69,014,170...69,276,457 		JBrowse link
G Akt1 AKT serine/threonine kinase 1 multiple interactions
increases phosphorylation		 ISO [Hydrogen Peroxide co-treated with loliolide] results in increased phosphorylation of AKT1 protein
loliolide results in increased phosphorylation of AKT1 protein		 CTD PMID:30231594 PMID:31601058 NCBI chr 6:131,713,716...131,735,319
Ensembl chr 6:131,713,720...131,733,921 		JBrowse link
G Alpl alkaline phosphatase, biomineralization associated increases expression ISO loliolide results in increased expression of ALPL mRNA CTD PMID:31601058 NCBI chr 5:149,951,397...150,006,424
Ensembl chr 5:149,951,409...150,006,446 		JBrowse link
G Bmp2 bone morphogenetic protein 2 increases expression ISO loliolide results in increased expression of BMP2 mRNA CTD PMID:31601058 NCBI chr 3:120,812,660...120,822,579
Ensembl chr 3:120,812,882...120,821,397 		JBrowse link
G Cdh1 cadherin 1 increases expression
multiple interactions		 ISO loliolide results in increased expression of CDH1 protein
loliolide inhibits the reaction [CXCL12 protein results in decreased expression of CDH1 protein]		 CTD PMID:36707041 NCBI chr19:34,492,371...34,561,775
Ensembl chr19:34,492,371...34,561,775 		JBrowse link
G Cdh2 cadherin 2 decreases expression ISO loliolide results in decreased expression of CDH2 protein CTD PMID:36707041 NCBI chr18:7,776,704...7,990,934
Ensembl chr18:7,776,704...7,990,167 		JBrowse link
G Cebpa CCAAT/enhancer binding protein alpha decreases expression ISO loliolide results in decreased expression of CEBPA protein CTD PMID:33567534 NCBI chr 1:87,759,631...87,762,303
Ensembl chr 1:87,759,433...87,762,412 		JBrowse link
G Creb1 cAMP responsive element binding protein 1 multiple interactions ISO loliolide inhibits the reaction [POMC protein alternative form results in increased phosphorylation of CREB1 protein] CTD PMID:30231594 NCBI chr 9:65,903,511...65,972,562
Ensembl chr 9:65,903,547...65,970,816 		JBrowse link
G Ctnnb1 catenin beta 1 multiple interactions ISO loliolide results in decreased phosphorylation of and affects the localization of and affects the activity of CTNNB1 protein CTD PMID:31601058 NCBI chr 8:120,640,008...120,667,110
Ensembl chr 8:120,639,995...120,667,111 		JBrowse link
G Cxcl12 C-X-C motif chemokine ligand 12 multiple interactions ISO loliolide inhibits the reaction [CXCL12 protein results in decreased expression of CDH1 protein]; loliolide inhibits the reaction [CXCL12 protein results in decreased expression of OCLN protein]; loliolide inhibits the reaction [CXCL12 protein results in increased expression of and results in increased activity of MMP2 protein]; loliolide inhibits the reaction [CXCL12 protein results in increased expression of and results in increased activity of MMP9 protein]; loliolide inhibits the reaction [CXCL12 protein results in increased expression of CXCR4 protein]; loliolide inhibits the reaction [CXCL12 protein results in increased expression of CXCR7 protein]; loliolide inhibits the reaction [CXCL12 protein results in increased expression of FN1 protein]; loliolide inhibits the reaction [CXCL12 protein results in increased expression of SNAI1 protein]; loliolide inhibits the reaction [CXCL12 protein results in increased expression of SOD2 protein]; loliolide inhibits the reaction [CXCL12 protein results in increased expression of TWIST1 protein]; loliolide inhibits the reaction [CXCL12 protein results in increased expression of VIM protein] CTD PMID:36707041 NCBI chr 4:150,388,326...150,401,173
Ensembl chr 4:150,388,325...150,401,168 		JBrowse link
G Cxcr4 C-X-C motif chemokine receptor 4 decreases expression
multiple interactions		 ISO loliolide results in decreased expression of CXCR4 protein
loliolide inhibits the reaction [CXCL12 protein results in increased expression of CXCR4 protein]; loliolide inhibits the reaction [SOD2 protein results in increased expression of CXCR4 protein]		 CTD PMID:36707041 NCBI chr13:40,077,976...40,081,883
Ensembl chr13:40,077,976...40,081,883 		JBrowse link
G Fabp4 fatty acid binding protein 4 decreases expression ISO loliolide results in decreased expression of FABP4 protein CTD PMID:33567534 NCBI chr 2:91,580,879...91,585,567
Ensembl chr 2:91,580,885...91,585,578 		JBrowse link
G Fasn fatty acid synthase decreases expression
multiple interactions		 ISO loliolide results in decreased expression of FASN protein
[loliolide co-treated with pinoresinol] results in decreased expression of FASN protein		 CTD PMID:31610126 NCBI chr10:106,072,093...106,090,259
Ensembl chr10:106,072,091...106,090,261 		JBrowse link
G Fgf7 fibroblast growth factor 7 increases expression ISO loliolide results in increased expression of FGF7 mRNA; loliolide results in increased expression of FGF7 protein CTD PMID:31601058 NCBI chr 3:113,280,448...113,333,279
Ensembl chr 3:113,281,283...113,332,929 		JBrowse link
G Fn1 fibronectin 1 multiple interactions
decreases expression		 ISO loliolide inhibits the reaction [CXCL12 protein results in increased expression of FN1 protein]
loliolide results in decreased expression of FN1 protein		 CTD PMID:36707041 NCBI chr 9:73,196,044...73,264,695
Ensembl chr 9:73,196,044...73,264,678 		JBrowse link
G Gsk3b glycogen synthase kinase 3 beta increases phosphorylation ISO loliolide results in increased phosphorylation of GSK3B protein CTD PMID:31601058 NCBI chr11:62,498,997...62,648,665
Ensembl chr11:62,504,316...62,648,646 		JBrowse link
G Hey1 hes-related family bHLH transcription factor with YRPW motif 1 increases expression ISO loliolide results in increased expression of HEY1 mRNA CTD PMID:31601058 NCBI chr 2:93,096,605...93,100,316
Ensembl chr 2:93,095,498...93,100,312 		JBrowse link
G Hmox1 heme oxygenase 1 multiple interactions ISO [Hydrogen Peroxide co-treated with loliolide] results in increased expression of HMOX1 mRNA CTD PMID:30231594 NCBI chr19:13,466,287...13,474,082
Ensembl chr19:13,467,244...13,474,079 		JBrowse link
G Igf1 insulin-like growth factor 1 increases expression ISO loliolide results in increased expression of IGF1 mRNA; loliolide results in increased expression of IGF1 protein CTD PMID:31601058 NCBI chr 7:22,282,895...22,361,972
Ensembl chr 7:22,282,930...22,359,296 		JBrowse link
G Jak1 Janus kinase 1 multiple interactions ISO loliolide inhibits the reaction [SOD2 protein results in increased phosphorylation of JAK1 protein] CTD PMID:36707041 NCBI chr 5:115,780,248...115,888,841
Ensembl chr 5:115,780,248...115,888,926 		JBrowse link
G Jak2 Janus kinase 2 multiple interactions ISO loliolide inhibits the reaction [SOD2 protein results in increased phosphorylation of JAK2 protein] CTD PMID:36707041 NCBI chr 1:226,995,334...227,054,381
Ensembl chr 1:226,995,334...227,054,189 		JBrowse link
G Lef1 lymphoid enhancer binding factor 1 increases expression
multiple interactions		 ISO loliolide results in increased expression of LEF1 mRNA
2-(4-morpholinyl)-8-phenyl-4H-1-benzopyran-4-one inhibits the reaction [loliolide results in increased expression of LEF1 mRNA]		 CTD PMID:31601058 NCBI chr 2:219,666,549...219,779,815
Ensembl chr 2:219,666,592...219,779,794 		JBrowse link
G Lipe lipase E, hormone sensitive type decreases expression ISO loliolide results in decreased expression of LIPE protein CTD PMID:33567534 NCBI chr 1:80,965,612...80,984,313
Ensembl chr 1:80,965,627...80,984,310 		JBrowse link
G Mitf melanocyte inducing transcription factor multiple interactions ISO loliolide inhibits the reaction [POMC protein alternative form results in increased expression of MITF protein] CTD PMID:30231594 NCBI chr 4:130,409,020...130,621,145
Ensembl chr 4:130,409,217...130,621,145 		JBrowse link
G Mmp1 matrix metallopeptidase 1 multiple interactions ISO loliolide inhibits the reaction [Hydrogen Peroxide results in increased expression of MMP1 mRNA] CTD PMID:30231594 NCBI chr 8:4,658,588...4,679,099
Ensembl chr 8:4,658,588...4,679,097 		JBrowse link
G Mmp2 matrix metallopeptidase 2 multiple interactions
decreases expression		 ISO loliolide inhibits the reaction [CXCL12 protein results in increased expression of and results in increased activity of MMP2 protein]; loliolide inhibits the reaction [Hydrogen Peroxide results in increased expression of MMP2 mRNA]
loliolide results in decreased expression of MMP2 protein		 CTD PMID:30231594 PMID:36707041 NCBI chr19:14,154,657...14,182,870
Ensembl chr19:14,154,657...14,182,870 		JBrowse link
G Mmp3 matrix metallopeptidase 3 multiple interactions ISO loliolide inhibits the reaction [Hydrogen Peroxide results in increased expression of MMP3 mRNA] CTD PMID:30231594 NCBI chr 8:4,640,397...4,653,963
Ensembl chr 8:4,640,416...4,653,961 		JBrowse link
G Mmp9 matrix metallopeptidase 9 multiple interactions
decreases expression		 ISO loliolide inhibits the reaction [CXCL12 protein results in increased expression of and results in increased activity of MMP9 protein]; loliolide inhibits the reaction [Hydrogen Peroxide results in increased expression of MMP9 mRNA]
loliolide results in decreased expression of MMP9 protein		 CTD PMID:30231594 PMID:36707041 NCBI chr 3:153,684,158...153,692,118
Ensembl chr 3:153,683,858...153,692,120 		JBrowse link
G Nfe2l2 NFE2 like bZIP transcription factor 2 multiple interactions ISO [Hydrogen Peroxide co-treated with loliolide] results in increased expression of NFE2L2 protein CTD PMID:30231594 NCBI chr 3:60,594,239...60,621,712
Ensembl chr 3:60,594,242...60,621,737 		JBrowse link
G Nr1h2 nuclear receptor subfamily 1, group H, member 2 multiple interactions ISO loliolide results in increased ubiquitination of and results in increased degradation of and results in decreased expression of NR1H2 protein CTD PMID:31610126 NCBI chr 1:95,041,967...95,047,358
Ensembl chr 1:95,041,967...95,047,377 		JBrowse link
G Nr1h3 nuclear receptor subfamily 1, group H, member 3 multiple interactions ISO loliolide results in increased ubiquitination of and results in increased degradation of and results in decreased expression of NR1H3 protein CTD PMID:31610126 NCBI chr 3:77,158,808...77,168,907
Ensembl chr 3:77,158,808...77,168,722 		JBrowse link
G Ocln occludin increases expression
multiple interactions		 ISO loliolide results in increased expression of OCLN protein
loliolide inhibits the reaction [CXCL12 protein results in decreased expression of OCLN protein]		 CTD PMID:36707041 NCBI chr 2:31,657,217...31,707,466
Ensembl chr 2:31,657,220...31,764,150 		JBrowse link
G Pomc proopiomelanocortin multiple interactions ISO loliolide inhibits the reaction [POMC protein alternative form results in increased expression of MITF protein]; loliolide inhibits the reaction [POMC protein alternative form results in increased expression of TYR protein]; loliolide inhibits the reaction [POMC protein alternative form results in increased phosphorylation of CREB1 protein] CTD PMID:30231594 NCBI chr 6:26,939,844...26,945,666
Ensembl chr 6:26,939,837...26,945,664 		JBrowse link
G Pparg peroxisome proliferator-activated receptor gamma decreases expression ISO loliolide results in decreased expression of PPARG protein CTD PMID:33567534 NCBI chr 4:148,423,102...148,548,471
Ensembl chr 4:148,423,194...148,548,468 		JBrowse link
G Ppargc1a PPARG coactivator 1 alpha decreases expression ISO loliolide results in decreased expression of PPARGC1A protein CTD PMID:33567534 NCBI chr14:58,860,752...59,516,525
Ensembl chr14:58,861,144...59,512,656 		JBrowse link
G Snai1 snail family transcriptional repressor 1 decreases expression
multiple interactions		 ISO loliolide results in decreased expression of SNAI1 protein
loliolide inhibits the reaction [CXCL12 protein results in increased expression of SNAI1 protein]		 CTD PMID:36707041 NCBI chr 3:156,248,479...156,252,969
Ensembl chr 3:156,248,485...156,252,969 		JBrowse link
G Sod2 superoxide dismutase 2 decreases expression
multiple interactions		 ISO loliolide results in decreased expression of SOD2 protein
loliolide inhibits the reaction [CXCL12 protein results in increased expression of SOD2 protein]; loliolide inhibits the reaction [SOD2 protein results in increased expression of CXCR4 protein]; loliolide inhibits the reaction [SOD2 protein results in increased expression of CXCR7 protein]; loliolide inhibits the reaction [SOD2 protein results in increased expression of SOD2 protein]; loliolide inhibits the reaction [SOD2 protein results in increased phosphorylation of JAK1 protein]; loliolide inhibits the reaction [SOD2 protein results in increased phosphorylation of JAK2 protein]; loliolide inhibits the reaction [SOD2 protein results in increased phosphorylation of STAT3 protein]		 CTD PMID:36707041 NCBI chr 1:47,638,318...47,645,163
Ensembl chr 1:47,636,528...47,645,189 		JBrowse link
G Srebf1 sterol regulatory element binding transcription factor 1 decreases expression
multiple interactions		 ISO loliolide results in decreased expression of SREBF1 protein
[loliolide co-treated with pinoresinol] results in decreased expression of SREBF1 protein		 CTD PMID:31610126 PMID:33567534 NCBI chr10:45,007,637...45,029,650
Ensembl chr10:45,007,637...45,029,650 		JBrowse link
G Stat3 signal transducer and activator of transcription 3 multiple interactions ISO loliolide inhibits the reaction [SOD2 protein results in increased phosphorylation of STAT3 protein] CTD PMID:36707041 NCBI chr10:85,811,206...85,863,057
Ensembl chr10:85,811,218...85,863,057 		JBrowse link
G Twist1 twist family bHLH transcription factor 1 multiple interactions
decreases expression		 ISO loliolide inhibits the reaction [CXCL12 protein results in increased expression of TWIST1 protein]
loliolide results in decreased expression of TWIST1 protein		 CTD PMID:36707041 NCBI chr 6:50,674,910...50,676,904
Ensembl chr 6:50,674,678...50,677,653 		JBrowse link
G Tyr tyrosinase multiple interactions ISO loliolide inhibits the reaction [POMC protein alternative form results in increased expression of TYR protein] CTD PMID:30231594 NCBI chr 1:141,115,036...141,210,207
Ensembl chr 1:141,115,036...141,210,207 		JBrowse link
G Vcan versican increases expression ISO loliolide results in increased expression of VCAN mRNA CTD PMID:31601058 NCBI chr 2:20,761,718...20,860,637
Ensembl chr 2:20,761,718...20,860,637 		JBrowse link
G Vegfa vascular endothelial growth factor A increases expression ISO loliolide results in increased expression of VEGFA mRNA; loliolide results in increased expression of VEGFA protein CTD PMID:31601058 NCBI chr 9:14,955,300...14,970,641
Ensembl chr 9:14,955,300...14,970,641 		JBrowse link
G Vim vimentin decreases expression
multiple interactions		 ISO loliolide results in decreased expression of VIM protein
loliolide inhibits the reaction [CXCL12 protein results in increased expression of VIM protein]		 CTD PMID:36707041 NCBI chr17:76,668,701...76,677,186
Ensembl chr17:76,668,647...76,677,187 		JBrowse link
G Wnt5a Wnt family member 5A increases expression
multiple interactions		 ISO loliolide results in increased expression of WNT5A mRNA
2-(4-morpholinyl)-8-phenyl-4H-1-benzopyran-4-one inhibits the reaction [loliolide results in increased expression of WNT5A mRNA]		 CTD PMID:31601058 NCBI chr16:3,697,032...3,718,230
Ensembl chr16:3,697,032...3,718,234 		JBrowse link
Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19898
    role 19868
      biological role 19866
        biochemical role 19571
          metabolite 19558
            loliolide 45
Path 2
Term Annotations click to browse term
  CHEBI ontology 19898
    subatomic particle 19896
      composite particle 19896
        hadron 19896
          baryon 19896
            nucleon 19896
              atomic nucleus 19896
                atom 19896
                  main group element atom 19835
                    p-block element atom 19835
                      carbon group element atom 19774
                        carbon atom 19771
                          organic molecular entity 19771
                            organic molecule 19724
                              organic cyclic compound 19515
                                organic heterocyclic compound 18890
                                  oxacycle 17918
                                    benzofurans 3289
                                      loliolide 45
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