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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:(Z)-3-butylidenephthalide
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Accession:CHEBI:68233 term browser browse the term
Definition:A gamma-lactone that is phthalide substituted by a butylidene group at position 3. Isolated from Ligusticum porteri, it exhibits hypoglycemic activity.
Synonyms:exact_synonym: (3Z)-3-butylidene-2-benzofuran-1(3H)-one
 related_synonym: Butylidenephthalide;   Formula=C12H12O2;   InChI=1S/C12H12O2/c1-2-3-8-11-9-6-4-5-7-10(9)12(13)14-11/h4-8H,2-3H2,1H3/b11-8-;   InChIKey=WMBOCUXXNSOQHM-FLIBITNWSA-N;   SMILES=CCC\\C=C1/OC(=O)c2ccccc12
 xref: CAS:551-08-6;   KEGG:C16924
 xref_mesh: MESH:C026105
 xref: PMID:20879744;   PMID:21553143;   PMID:22506278;   PMID:23400915;   PMID:23770345;   Reaxys:4231353


show annotations for term's descendants           Sort by:
(Z)-3-butylidenephthalide term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Ahr aryl hydrocarbon receptor multiple interactions ISO [butylidenephthalide co-treated with ligustilide] inhibits the reaction [Tetrachlorodibenzodioxin results in increased activity of AHR protein]; butylidenephthalide inhibits the reaction [Tetrachlorodibenzodioxin results in increased activity of AHR protein] CTD PMID:29191726 NCBI chr 6:52,234,089...52,271,568
Ensembl chr 6:52,234,089...52,271,568 		JBrowse link
G Aifm1 apoptosis inducing factor, mitochondria associated 1 increases expression EXP
ISO		 butylidenephthalide results in increased expression of AIFM1 protein CTD PMID:16987298 PMID:23770345 NCBI chr  X:127,650,223...127,689,356
Ensembl chr  X:127,650,226...127,689,256 		JBrowse link
G Anxa5 annexin A5 decreases expression ISO butylidenephthalide results in decreased expression of ANXA5 protein CTD PMID:23770345 NCBI chr 2:119,314,007...119,344,703
Ensembl chr 2:119,314,007...119,353,369 		JBrowse link
G Arhgap1 Rho GTPase activating protein 1 increases expression ISO butylidenephthalide results in increased expression of ARHGAP1 protein CTD PMID:23770345 NCBI chr 3:77,621,377...77,643,400
Ensembl chr 3:77,620,655...77,643,396 		JBrowse link
G Arhgdia Rho GDP dissociation inhibitor alpha increases expression ISO butylidenephthalide results in increased expression of ARHGDIA protein CTD PMID:23770345 NCBI chr10:105,854,526...105,858,020
Ensembl chr10:105,854,533...105,858,023 		JBrowse link
G Atp5f1a ATP synthase F1 subunit alpha increases expression ISO butylidenephthalide results in increased expression of ATP5F1A protein CTD PMID:23770345 NCBI chr18:71,292,406...71,300,342
Ensembl chr18:71,292,374...71,300,794 		JBrowse link
G Atp5f1b ATP synthase F1 subunit beta decreases expression ISO butylidenephthalide results in decreased expression of ATP5F1B protein CTD PMID:23770345 NCBI chr 7:515,454...521,858
Ensembl chr 7:515,460...567,273 		JBrowse link
G Bax BCL2 associated X, apoptosis regulator increases expression EXP
ISO		 butylidenephthalide results in increased expression of BAX protein CTD PMID:16987298 NCBI chr 1:95,940,001...95,945,407
Ensembl chr 1:95,938,808...95,945,368 		JBrowse link
G Bik BCL2-interacting killer increases expression ISO butylidenephthalide results in increased expression of BIK protein CTD PMID:23770345 NCBI chr 7:114,672,277...114,691,296
Ensembl chr 7:114,672,277...114,691,296 		JBrowse link
G C1qbp complement C1q binding protein increases expression ISO butylidenephthalide results in increased expression of C1QBP protein CTD PMID:23770345 NCBI chr10:55,699,954...55,704,605
Ensembl chr10:55,699,954...55,704,649 		JBrowse link
G Calr calreticulin decreases expression ISO butylidenephthalide results in decreased expression of CALR protein CTD PMID:23770345 NCBI chr19:23,308,525...23,313,420
Ensembl chr19:23,308,351...23,313,414 		JBrowse link
G Casp3 caspase 3 increases cleavage ISO
EXP		 butylidenephthalide results in increased cleavage of CASP3 protein CTD PMID:16987298 NCBI chr16:45,662,910...45,681,171
Ensembl chr16:45,662,910...45,684,648 		JBrowse link
G Casp8 caspase 8 increases cleavage ISO
EXP		 butylidenephthalide results in increased cleavage of CASP8 protein CTD PMID:16987298 NCBI chr 9:60,263,863...60,312,542
Ensembl chr 9:60,264,075...60,312,542 		JBrowse link
G Casp9 caspase 9 increases cleavage EXP
ISO		 butylidenephthalide results in increased cleavage of CASP9 protein CTD PMID:16987298 NCBI chr 5:154,108,872...154,126,628
Ensembl chr 5:154,109,046...154,126,626 		JBrowse link
G Ccnd1 cyclin D1 decreases expression EXP
ISO		 butylidenephthalide results in decreased expression of CCND1 protein CTD PMID:16987298 PMID:23770345 NCBI chr 1:200,089,002...200,098,524
Ensembl chr 1:200,089,002...200,098,602 		JBrowse link
G Ccne1 cyclin E1 decreases expression ISO
EXP		 butylidenephthalide results in decreased expression of CCNE1 protein CTD PMID:16987298 NCBI chr 1:90,781,947...90,791,188
Ensembl chr 1:90,781,949...90,791,101 		JBrowse link
G Cdk2 cyclin dependent kinase 2 decreases expression EXP
ISO		 butylidenephthalide results in decreased expression of CDK2 protein CTD PMID:16987298 PMID:23770345 NCBI chr 7:1,129,878...1,137,431
Ensembl chr 7:1,129,811...1,137,403 		JBrowse link
G Cdk4 cyclin-dependent kinase 4 decreases expression EXP
ISO		 butylidenephthalide results in decreased expression of CDK4 protein CTD PMID:16987298 NCBI chr 7:62,885,647...62,889,562
Ensembl chr 7:62,883,105...62,942,403 		JBrowse link
G Cdk6 cyclin-dependent kinase 6 decreases expression EXP
ISO		 butylidenephthalide results in decreased expression of CDK6 protein CTD PMID:16987298 NCBI chr 4:30,637,650...30,829,688
Ensembl chr 4:30,646,460...30,829,634 		JBrowse link
G Cdkn1a cyclin-dependent kinase inhibitor 1A decreases expression
increases expression		 EXP
ISO		 butylidenephthalide results in decreased expression of CDKN1A protein
butylidenephthalide results in increased expression of CDKN1A protein		 CTD PMID:16987298 PMID:23770345 NCBI chr20:7,149,177...7,159,727
Ensembl chr20:7,149,217...7,159,585 		JBrowse link
G Cdkn1b cyclin-dependent kinase inhibitor 1B increases expression EXP butylidenephthalide results in increased expression of CDKN1B protein CTD PMID:16987298 NCBI chr 4:167,760,067...167,765,177
Ensembl chr 4:167,760,181...167,764,982 		JBrowse link
G Cdkn2a cyclin-dependent kinase inhibitor 2A increases expression ISO butylidenephthalide results in increased expression of CDKN2A protein CTD PMID:16987298 PMID:23770345 NCBI chr 5:103,984,949...103,992,143
Ensembl chr 5:103,984,949...104,003,149 		JBrowse link
G Cycs cytochrome c, somatic increases expression ISO butylidenephthalide results in increased expression of CYCS protein CTD PMID:23770345 NCBI chr 4:79,651,894...79,653,994
Ensembl chr 4:79,651,378...79,654,054 		JBrowse link
G Cyp1a1 cytochrome P450, family 1, subfamily a, polypeptide 1 multiple interactions
increases expression		 ISO butylidenephthalide inhibits the reaction [Tetrachlorodibenzodioxin results in increased expression of CYP1A1 mRNA]
butylidenephthalide results in increased expression of CYP1A1 mRNA		 CTD PMID:29191726 NCBI chr 8:58,096,021...58,102,130
Ensembl chr 8:58,096,077...58,102,125 		JBrowse link
G Ddit3 DNA-damage inducible transcript 3 increases expression ISO butylidenephthalide results in increased expression of DDIT3 protein CTD PMID:23770345 NCBI chr 7:63,115,645...63,121,203
Ensembl chr 7:63,116,380...63,121,201 		JBrowse link
G Eef1a1 eukaryotic translation elongation factor 1 alpha 1 decreases expression ISO butylidenephthalide results in decreased expression of EEF1A1 protein CTD PMID:23770345 NCBI chr 8:79,341,554...79,344,784
Ensembl chr 8:79,341,557...79,344,839 		JBrowse link
G Eef1a2 eukaryotic translation elongation factor 1 alpha 2 decreases expression ISO butylidenephthalide results in decreased expression of EEF1A2 protein CTD PMID:23770345 NCBI chr 3:168,265,893...168,275,071
Ensembl chr 3:168,195,357...168,275,071 		JBrowse link
G Eef2 eukaryotic translation elongation factor 2 increases expression ISO butylidenephthalide results in increased expression of EEF2 protein CTD PMID:23770345 NCBI chr 7:8,533,248...8,538,518
Ensembl chr 7:8,533,116...8,559,183 		JBrowse link
G Eif4a1 eukaryotic translation initiation factor 4A1 decreases expression ISO butylidenephthalide results in decreased expression of EIF4A1 protein CTD PMID:23770345 NCBI chr10:54,384,345...54,389,853
Ensembl chr10:54,384,347...54,389,858 		JBrowse link
G Elavl1 ELAV like RNA binding protein 1 decreases expression ISO butylidenephthalide results in decreased expression of ELAVL1 protein CTD PMID:23770345 NCBI chr12:2,640,936...2,684,787
Ensembl chr12:2,645,061...2,684,784 		JBrowse link
G Eno1 enolase 1 decreases expression ISO butylidenephthalide results in decreased expression of ENO1 protein CTD PMID:23770345 NCBI chr 5:160,719,951...160,731,337
Ensembl chr 5:160,719,951...160,731,336 		JBrowse link
G Ern1 endoplasmic reticulum to nucleus signaling 1 increases expression ISO butylidenephthalide results in increased expression of ERN1 protein CTD PMID:23770345 NCBI chr10:91,326,889...91,421,201
Ensembl chr10:91,330,654...91,421,029 		JBrowse link
G Fas Fas cell surface death receptor increases expression ISO butylidenephthalide results in increased expression of FAS protein CTD PMID:16987298 PMID:23770345 NCBI chr 1:231,798,963...231,832,591
Ensembl chr 1:231,798,960...231,832,591 		JBrowse link
G Fus Fus RNA binding protein increases expression ISO butylidenephthalide results in increased expression of FUS protein CTD PMID:23770345 NCBI chr 1:182,576,479...182,590,417
Ensembl chr 1:182,576,545...182,590,414 		JBrowse link
G Got1 glutamic-oxaloacetic transaminase 1 increases expression ISO butylidenephthalide results in increased expression of GOT1 protein CTD PMID:23770345 NCBI chr 1:242,357,293...242,381,535
Ensembl chr 1:242,357,306...242,380,633 		JBrowse link
G Hnrnpa3 heterogeneous nuclear ribonucleoprotein A3 decreases expression ISO butylidenephthalide results in decreased expression of HNRNPA3 protein CTD PMID:23770345 NCBI chr 3:60,578,574...60,588,755
Ensembl chr 3:60,578,673...60,588,306 		JBrowse link
G Hnrnpd heterogeneous nuclear ribonucleoprotein D increases expression ISO butylidenephthalide results in increased expression of HNRNPD protein CTD PMID:23770345 NCBI chr14:9,615,375...9,638,975
Ensembl chr14:9,615,479...9,633,786 		JBrowse link
G Hnrnpf heterogeneous nuclear ribonucleoprotein F decreases expression ISO butylidenephthalide results in decreased expression of HNRNPF protein CTD PMID:23770345 NCBI chr 4:151,083,262...151,104,464
Ensembl chr 4:151,083,062...151,109,038 		JBrowse link
G Hsp90ab1 heat shock protein 90 alpha family class B member 1 decreases expression ISO butylidenephthalide results in decreased expression of HSP90AB1 protein CTD PMID:23770345 NCBI chr 9:15,432,986...15,438,358
Ensembl chr 9:15,433,691...15,438,488 		JBrowse link
G Hspa5 heat shock protein family A (Hsp70) member 5 increases expression ISO butylidenephthalide results in increased expression of HSPA5 protein CTD PMID:23770345 NCBI chr 3:18,055,507...18,059,969
Ensembl chr 3:18,055,405...18,059,891 		JBrowse link
G Ldha lactate dehydrogenase A decreases expression ISO butylidenephthalide results in decreased expression of LDHA protein CTD PMID:23770345 NCBI chr 1:97,371,823...97,381,247
Ensembl chr 1:97,366,021...97,433,472 		JBrowse link
G Mif macrophage migration inhibitory factor increases expression ISO butylidenephthalide results in increased expression of MIF protein CTD PMID:23770345 NCBI chr20:12,790,919...12,791,784
Ensembl chr20:12,790,902...12,799,504 		JBrowse link
G Mki67 marker of proliferation Ki-67 decreases expression ISO
EXP		 butylidenephthalide results in decreased expression of MKI67 protein CTD PMID:16987298 NCBI chr 1:190,496,319...190,522,983
Ensembl chr 1:190,496,319...190,522,762 		JBrowse link
G Ncl nucleolin decreases expression ISO butylidenephthalide results in decreased expression of NCL protein CTD PMID:23770345 NCBI chr 9:86,999,588...87,008,112
Ensembl chr 9:86,998,019...87,008,136 		JBrowse link
G Nme1 NME/NM23 nucleoside diphosphate kinase 1 increases expression ISO butylidenephthalide results in increased expression of NME1 protein CTD PMID:23770345 NCBI chr10:78,907,036...78,929,659
Ensembl chr10:78,906,083...78,916,408 		JBrowse link
G Pcna proliferating cell nuclear antigen decreases expression ISO butylidenephthalide results in decreased expression of PCNA protein CTD PMID:23770345 NCBI chr 3:119,499,039...119,502,911
Ensembl chr 3:119,498,810...119,502,995 		JBrowse link
G Pgk1 phosphoglycerate kinase 1 decreases expression ISO butylidenephthalide results in decreased expression of PGK1 protein CTD PMID:23770345 NCBI chr  X:71,271,454...71,287,429
Ensembl chr  X:71,271,440...71,287,418 		JBrowse link
G Phb1 prohibitin 1 decreases expression ISO butylidenephthalide results in decreased expression of PHB1 protein CTD PMID:23770345 NCBI chr10:80,605,268...80,618,043
Ensembl chr10:80,605,251...80,618,042 		JBrowse link
G Ppp2r1a protein phosphatase 2 scaffold subunit A alpha increases expression ISO butylidenephthalide results in increased expression of PPP2R1A protein CTD PMID:23770345 NCBI chr 1:60,540,223...60,559,467
Ensembl chr 1:60,540,194...60,560,129 		JBrowse link
G Prps1 phosphoribosyl pyrophosphate synthetase 1 decreases expression ISO butylidenephthalide results in decreased expression of PRPS1 protein CTD PMID:23770345 NCBI chr  X:104,132,139...104,154,191
Ensembl chr  X:104,132,141...104,154,187 		JBrowse link
G Psma1 proteasome 20S subunit alpha 1 increases expression ISO butylidenephthalide results in increased expression of PSMA1 protein CTD PMID:23770345 NCBI chr 1:168,442,421...168,453,440
Ensembl chr 1:168,440,936...168,453,472 		JBrowse link
G Psmd11 proteasome 26S subunit, non-ATPase 11 decreases expression ISO butylidenephthalide results in decreased expression of PSMD11 protein CTD PMID:23770345 NCBI chr10:65,433,853...65,479,774
Ensembl chr10:65,433,853...65,479,766 		JBrowse link
G Rb1 RB transcriptional corepressor 1 decreases phosphorylation ISO
EXP		 butylidenephthalide results in decreased phosphorylation of RB1 protein CTD PMID:16987298 NCBI chr15:48,371,295...48,502,473
Ensembl chr15:48,371,296...48,502,302 		JBrowse link
G Rpsa ribosomal protein SA decreases expression ISO butylidenephthalide results in decreased expression of RPSA protein CTD PMID:23770345 NCBI chr 8:119,851,225...119,855,103
Ensembl chr 8:119,851,225...119,855,247 		JBrowse link
G Sf3b3 splicing factor 3b, subunit 3 increases expression ISO butylidenephthalide results in increased expression of SF3B3 protein CTD PMID:23770345 NCBI chr19:38,782,749...38,820,271
Ensembl chr19:38,783,040...38,820,245 		JBrowse link
G Sfn stratifin increases expression ISO butylidenephthalide results in increased expression of SFN protein CTD PMID:23770345 Ensembl chr 5:145,826,201...145,831,314 JBrowse link
G Tp53 tumor protein p53 increases expression
increases phosphorylation		 ISO butylidenephthalide results in increased expression of TP53 protein
butylidenephthalide results in increased phosphorylation of TP53 protein		 CTD PMID:16987298 NCBI chr10:54,300,070...54,311,525
Ensembl chr10:54,300,048...54,311,524 		JBrowse link
G Tpt1 tumor protein, translationally-controlled 1 decreases expression ISO butylidenephthalide results in decreased expression of TPT1 protein CTD PMID:23770345 NCBI chr15:51,156,728...51,159,629
Ensembl chr15:51,146,154...51,159,625 		JBrowse link
G Tufm Tu translation elongation factor, mitochondrial increases expression ISO butylidenephthalide results in increased expression of TUFM protein CTD PMID:23770345 NCBI chr 1:181,073,788...181,077,395
Ensembl chr 1:181,073,788...181,077,395 		JBrowse link
G Was WASP actin nucleation promoting factor decreases expression ISO butylidenephthalide results in decreased expression of WAS protein CTD PMID:23770345 NCBI chr  X:14,405,096...14,413,850
Ensembl chr  X:14,405,124...14,413,849 		JBrowse link
G Ybx1 Y box binding protein 1 decreases expression ISO butylidenephthalide results in decreased expression of YBX1 protein CTD PMID:23770345 NCBI chr 5:132,882,137...132,899,108
Ensembl chr 5:132,882,145...132,898,862 		JBrowse link
Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19818
    role 19790
      biological role 19788
        biochemical role 19501
          metabolite 19486
            (Z)-3-butylidenephthalide 61
Path 2
Term Annotations click to browse term
  CHEBI ontology 19818
    subatomic particle 19816
      composite particle 19816
        hadron 19816
          baryon 19816
            nucleon 19816
              atomic nucleus 19816
                atom 19816
                  main group element atom 19761
                    p-block element atom 19761
                      carbon group element atom 19703
                        carbon atom 19698
                          organic molecular entity 19698
                            organic group 18905
                              organic divalent group 18887
                                organodiyl group 18887
                                  carbonyl group 18853
                                    carbonyl compound 18853
                                      carboxylic ester 15998
                                        lactone 11443
                                          gamma-lactone 6852
                                            2-benzofuran-1(3H)-one 93
                                              (Z)-3-butylidenephthalide 61
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