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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


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(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 6:54,963,990...55,001,806
Ensembl chr 6:54,963,990...55,001,464
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:135,304,063...135,343,062
Ensembl chr  X:135,304,066...135,343,087
JBrowse link
G Anxa5 annexin A5 decreases expression ISO butylidenephthalide results in decreased expression of ANXA5 protein CTD PMID:23770345 NCBI chr 2:123,162,477...123,194,730
Ensembl chr 2:123,162,461...123,193,130
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 3:80,555,196...80,576,881
Ensembl chr 3:80,555,196...80,576,856
JBrowse link
G Arhgdia Rho GDP dissociation inhibitor alpha increases expression ISO butylidenephthalide results in increased expression of ARHGDIA protein CTD PMID:23770345 NCBI chr10:109,754,012...109,757,506
Ensembl chr10:109,754,004...109,757,550
JBrowse link
G Atp5f1a ATP synthase F1 subunit alpha increases expression ISO butylidenephthalide results in increased expression of ATP5F1A protein CTD PMID:23770345 NCBI chr18:74,156,553...74,164,490
Ensembl chr18:74,156,553...74,164,495
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 7:2,504,708...2,511,748
Ensembl chr 7:2,504,695...2,511,749
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 1:101,451,801...101,457,207
Ensembl chr 1:101,451,802...101,457,207
JBrowse link
G Bik BCL2-interacting killer increases expression ISO butylidenephthalide results in increased expression of BIK protein CTD PMID:23770345 NCBI chr 7:124,390,924...124,410,449
Ensembl chr 7:124,391,432...124,410,447
JBrowse link
G C1qbp complement C1q binding protein increases expression ISO butylidenephthalide results in increased expression of C1QBP protein CTD PMID:23770345 NCBI chr10:57,613,876...57,618,527
Ensembl chr10:57,613,879...57,618,527
JBrowse link
G Calr calreticulin decreases expression ISO butylidenephthalide results in decreased expression of CALR protein CTD PMID:23770345 NCBI chr19:25,956,771...25,961,666
Ensembl chr19:25,956,771...25,961,666
JBrowse link
G Casp3 caspase 3 increases cleavage ISO
EXP
butylidenephthalide results in increased cleavage of CASP3 protein CTD PMID:16987298 NCBI chr16:48,845,011...48,863,249
Ensembl chr16:48,845,012...48,863,204
JBrowse link
G Casp8 caspase 8 increases cleavage ISO
EXP
butylidenephthalide results in increased cleavage of CASP8 protein CTD PMID:16987298 NCBI chr 9:65,614,142...65,662,624
Ensembl chr 9:65,614,142...65,662,106
JBrowse link
G Casp9 caspase 9 increases cleavage EXP
ISO
butylidenephthalide results in increased cleavage of CASP9 protein CTD PMID:16987298 NCBI chr 5:160,356,211...160,373,774
Ensembl chr 5:160,355,833...160,373,778
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 1:218,090,750...218,100,447
Ensembl chr 1:218,090,750...218,100,325
JBrowse link
G Ccne1 cyclin E1 decreases expression ISO
EXP
butylidenephthalide results in decreased expression of CCNE1 protein CTD PMID:16987298 NCBI chr 1:94,485,830...94,495,112
Ensembl chr 1:94,485,832...94,494,980
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 7:3,124,953...3,132,533
Ensembl chr 7:3,124,954...3,132,457
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 7:70,345,971...70,352,689
Ensembl chr 7:70,349,863...70,352,418
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 4:27,781,728...27,969,653
Ensembl chr 4:27,785,647...27,966,398
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 chr20:6,348,422...6,358,864
Ensembl chr20:6,351,458...6,358,864
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 4:168,689,043...168,694,159
Ensembl chr 4:168,689,163...168,693,964
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 5:107,823,323...107,832,405
Ensembl chr 5:107,823,330...107,841,175
JBrowse link
G Cycs cytochrome c, somatic increases expression ISO butylidenephthalide results in increased expression of CYCS protein CTD PMID:23770345 NCBI chr 4:80,331,226...80,333,326
Ensembl chr 4:80,331,227...80,333,326
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 8:62,472,087...62,478,122
Ensembl chr 8:62,472,095...62,478,147
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 7:70,578,564...70,585,074
Ensembl chr 7:70,580,198...70,585,084
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 8:85,838,594...85,841,816
Ensembl chr 8:85,838,869...85,840,818
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 3:176,657,104...176,666,282
Ensembl chr 3:176,657,107...176,666,282
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 7:11,401,501...11,406,771
Ensembl chr 7:11,401,501...11,406,771
JBrowse link
G Eif4a1 eukaryotic translation initiation factor 4A1 decreases expression ISO butylidenephthalide results in decreased expression of EIF4A1 protein CTD PMID:23770345 NCBI chr10:56,271,257...56,276,764
Ensembl chr10:56,271,257...56,276,764
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 chr12:2,461,502...2,502,432
Ensembl chr12:2,461,502...2,502,432
JBrowse link
G Eno1 enolase 1 decreases expression ISO butylidenephthalide results in decreased expression of ENO1 protein CTD PMID:23770345 NCBI chr 5:167,288,223...167,299,610
Ensembl chr 5:167,288,223...167,299,609
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 chr10:94,588,555...94,682,072
Ensembl chr10:94,588,555...94,681,914
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 1:252,589,785...252,624,790
Ensembl chr 1:252,589,785...252,624,790
JBrowse link
G Fus FUS RNA binding protein increases expression ISO butylidenephthalide results in increased expression of FUS protein CTD PMID:23770345 NCBI chr 1:199,412,805...199,426,705
Ensembl chr 1:199,412,834...199,426,702
JBrowse link
G Got1 glutamic-oxaloacetic transaminase 1 increases expression ISO butylidenephthalide results in increased expression of GOT1 protein CTD PMID:23770345 NCBI chr 1:263,246,248...263,269,762
Ensembl chr 1:263,246,248...263,269,762
JBrowse link
G Hnrnpa3 heterogeneous nuclear ribonucleoprotein A3 decreases expression ISO butylidenephthalide results in decreased expression of HNRNPA3 protein CTD PMID:23770345 NCBI chr 3:62,481,222...62,491,356
Ensembl chr 3:62,481,323...62,487,227
JBrowse link
G Hnrnpd heterogeneous nuclear ribonucleoprotein D increases expression ISO butylidenephthalide results in increased expression of HNRNPD protein CTD PMID:23770345 NCBI chr14:11,256,163...11,274,684
Ensembl chr14:11,256,268...11,274,578
JBrowse link
G Hnrnpf heterogeneous nuclear ribonucleoprotein F decreases expression ISO butylidenephthalide results in decreased expression of HNRNPF protein CTD PMID:23770345 NCBI chr 4:149,957,143...149,978,896
Ensembl chr 4:149,957,206...149,978,895
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 9:17,817,791...17,823,163
Ensembl chr 9:17,817,721...17,823,243
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 3:13,838,304...13,842,763
Ensembl chr 3:13,838,304...13,842,762
JBrowse link
G Ldha lactate dehydrogenase A decreases expression ISO butylidenephthalide results in decreased expression of LDHA protein CTD PMID:23770345 NCBI chr 1:102,900,288...102,909,713
Ensembl chr 1:102,900,286...102,909,707
JBrowse link
G Mif macrophage migration inhibitory factor increases expression ISO butylidenephthalide results in increased expression of MIF protein CTD PMID:23770345 NCBI chr20:13,715,219...13,732,980
Ensembl chr20:13,732,198...13,732,859
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 1:207,993,895...208,020,454
Ensembl chr 1:207,993,895...208,020,454
JBrowse link
G Ncl nucleolin decreases expression ISO butylidenephthalide results in decreased expression of NCL protein CTD PMID:23770345 NCBI chr 9:93,369,119...93,377,643
Ensembl chr 9:93,368,932...93,377,643
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 chr10:81,657,152...81,666,542
Ensembl chr10:81,657,153...81,666,523
JBrowse link
G Pcna proliferating cell nuclear antigen decreases expression ISO butylidenephthalide results in decreased expression of PCNA protein CTD PMID:23770345 NCBI chr 3:124,880,698...124,884,570
Ensembl chr 3:124,880,698...124,884,570
JBrowse link
G Pgk1 phosphoglycerate kinase 1 decreases expression ISO butylidenephthalide results in decreased expression of PGK1 protein CTD PMID:23770345 NCBI chr  X:77,263,399...77,279,373
Ensembl chr  X:77,263,359...77,279,367
JBrowse link
G Phb prohibitin decreases expression ISO butylidenephthalide results in decreased expression of PHB protein CTD PMID:23770345 NCBI chr10:83,476,107...83,488,878
Ensembl chr10:83,476,107...83,488,878
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 1:60,717,386...60,736,629
Ensembl chr 1:60,717,386...60,736,609
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:111,798,233...111,820,270
Ensembl chr  X:111,798,233...111,820,266
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 1:183,733,567...183,744,586
Ensembl chr 1:183,733,567...183,744,586
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 chr10:67,810,655...67,857,562
Ensembl chr10:67,810,655...67,857,223
JBrowse link
G Rb1 RB transcriptional corepressor 1 decreases phosphorylation ISO
EXP
butylidenephthalide results in decreased phosphorylation of RB1 protein CTD PMID:16987298 NCBI chr15:55,081,582...55,209,060
Ensembl chr15:55,083,140...55,209,342
JBrowse link
G Rpsa ribosomal protein SA decreases expression ISO butylidenephthalide results in decreased expression of RPSA protein CTD PMID:23770345 NCBI chr 8:128,806,053...128,809,987
Ensembl chr 8:128,806,129...128,809,986
JBrowse link
G Sf3b3 splicing factor 3b, subunit 3 increases expression ISO butylidenephthalide results in increased expression of SF3B3 protein CTD PMID:23770345 NCBI chr19:43,392,071...43,429,582
Ensembl chr19:43,392,085...43,429,580
JBrowse link
G Sfn stratifin increases expression ISO butylidenephthalide results in increased expression of SFN protein CTD PMID:23770345 NCBI chr 5:151,823,422...151,824,937
Ensembl chr 5:151,823,887...151,824,633
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 chr10:56,186,299...56,198,449
Ensembl chr10:56,187,020...56,198,449
JBrowse link
G Tpt1 tumor protein, translationally-controlled 1 decreases expression ISO butylidenephthalide results in decreased expression of TPT1 protein CTD PMID:23770345 NCBI chr15:57,891,680...57,894,504
Ensembl chr15:57,891,680...57,894,504
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 1:197,903,582...197,907,189
Ensembl chr 1:197,903,582...197,907,189
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:15,155,246...15,164,099
Ensembl chr  X:15,155,230...15,164,105
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 5:138,319,754...138,336,721
Ensembl chr 5:138,319,762...138,336,475
JBrowse link

Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19785
    role 19732
      biological role 19732
        biochemical role 19281
          metabolite 19262
            (Z)-3-butylidenephthalide 61
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 ester 14073
                                        lactone 5978
                                          gamma-lactone 1214
                                            2-benzofuran-1(3H)-one 91
                                              (Z)-3-butylidenephthalide 61
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RGD is funded by grant HL64541 from the National Heart, Lung, and Blood Institute on behalf of the NIH.