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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:withaferin A
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Accession:CHEBI:69120 term browser browse the term
Definition:A withanolide that is 5,6:22,26-diepoxyergosta-2,24-diene-1,26-dione substituted by hydroxy groups at positions 4 and 27 (the 4beta,5beta,6beta,22R stereoisomer). Isolated from Physalis longifolia, it exhibits cytotoxic activity.
Synonyms:exact_synonym: (4beta,5beta,6beta,22R)-4,27-dihydroxy-5,6:22,26-diepoxyergosta-2,24-diene-1,26-dione
 related_synonym: 4beta,27-dihydroxy-1-oxo-5beta,6beta-epoxywitha-2,24-dienolide;   Formula=C28H38O6;   InChI=1S/C28H38O6/c1-14-11-21(33-25(32)17(14)13-29)15(2)18-5-6-19-16-12-24-28(34-24)23(31)8-7-22(30)27(28,4)20(16)9-10-26(18,19)3/h7-8,15-16,18-21,23-24,29,31H,5-6,9-13H2,1-4H3/t15-,16-,18+,19-,20-,21+,23-,24+,26+,27-,28+/m0/s1;   InChIKey=DBRXOUCRJQVYJQ-CKNDUULBSA-N;   SMILES=C[C@@H]([C@H]1CC[C@H]2[C@@H]3C[C@H]4O[C@]44[C@@H](O)C=CC(=O)[C@]4(C)[C@H]3CC[C@]12C)[C@H]1CC(C)=C(CO)C(=O)O1
 alt_id: CHEBI:10040
 xref: CAS:5119-48-2;   KEGG:C08841;   KNApSAcK:C00003676
 xref_mesh: MESH:C009684
 xref: PMID:22098611;   PMID:22935676;   PMID:22989414;   PMID:23107437;   PMID:23129310;   PMID:23318585;   PMID:23821767;   Patent:WO2010030395;   Patent:WO2010053655;   Reaxys:6284722;   Wikipedia:Withaferin_A

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withaferin A term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Abcb1a ATP binding cassette subfamily B member 1A multiple interactions ISO withaferin A inhibits the reaction [[ABCB1 protein results in decreased susceptibility to Doxorubicin] promotes the reaction [Tetradecanoylphorbol Acetate results in increased expression of ABCB1 mRNA]] CTD PMID:20438634 NCBI chr 4:25,357,467...25,529,941
Ensembl chr 4:25,158,362...25,442,709 		JBrowse link
G Adam17 ADAM metallopeptidase domain 17 multiple interactions ISO withaferin A inhibits the reaction [IL1B protein promotes the reaction [ADAM17 protein results in increased cleavage of PROCR protein]]; withaferin A inhibits the reaction [Tetradecanoylphorbol Acetate promotes the reaction [ADAM17 protein results in increased cleavage of PROCR protein]]; withaferin A inhibits the reaction [Tetradecanoylphorbol Acetate results in increased expression of and results in increased activity of ADAM17 protein]; withaferin A inhibits the reaction [TNF protein promotes the reaction [ADAM17 protein results in increased cleavage of PROCR protein]] CTD PMID:24632454 NCBI chr 6:40,872,936...40,920,700
Ensembl chr 6:40,872,856...40,920,639 		JBrowse link
G Atf4 activating transcription factor 4 multiple interactions
increases expression		 ISO Acetylcysteine inhibits the reaction [withaferin A results in increased expression of ATF4 protein] CTD PMID:21266191 NCBI chr 7:111,804,135...111,806,457
Ensembl chr 7:111,804,183...111,806,446 		JBrowse link
G Bad BCL2-associated agonist of cell death multiple interactions ISO withaferin A results in decreased expression of and results in decreased phosphorylation of BAD protein CTD PMID:20438634 NCBI chr 1:204,133,502...204,142,829
Ensembl chr 1:204,131,501...204,142,823 		JBrowse link
G Bcl2 BCL2, apoptosis regulator decreases expression ISO withaferin A results in decreased expression of BCL2 protein CTD PMID:20438634 PMID:21256832 PMID:21964475 NCBI chr13:22,689,783...22,853,920 JBrowse link
G Bcl2a1 BCL2-related protein A1 multiple interactions ISO withaferin A inhibits the reaction [Tetradecanoylphorbol Acetate results in increased expression of BCL2A1 mRNA] CTD PMID:20438634 NCBI chr 8:89,716,914...89,724,998
Ensembl chr 8:89,716,914...89,724,998 		JBrowse link
G Bcl2l11 BCL2 like 11 decreases expression ISO withaferin A results in decreased expression of BCL2L11 protein CTD PMID:20438634 NCBI chr 3:115,366,783...115,404,068
Ensembl chr 3:115,366,646...115,404,068 		JBrowse link
G Ccl2 C-C motif chemokine ligand 2 multiple interactions ISO withaferin A inhibits the reaction [Tetradecanoylphorbol Acetate results in increased expression of CCL2 mRNA] CTD PMID:20438634 NCBI chr10:67,005,424...67,007,222
Ensembl chr10:67,005,424...67,007,226 		JBrowse link
G Ccnd1 cyclin D1 multiple interactions ISO withaferin A inhibits the reaction [Tetradecanoylphorbol Acetate results in increased expression of CCND1 mRNA] CTD PMID:20438634 NCBI chr 1:200,089,002...200,098,524
Ensembl chr 1:200,089,002...200,098,602 		JBrowse link
G Cdkn1a cyclin-dependent kinase inhibitor 1A affects binding
multiple interactions
increases expression		 ISO withaferin A binds to CDKN1A protein
withaferin A results in increased expression of and affects the localization of CDKN1A protein
withaferin A results in increased expression of CDKN1A mRNA		 CTD PMID:22973447 NCBI chr20:7,149,177...7,159,727
Ensembl chr20:7,149,217...7,159,585 		JBrowse link
G Cdkn2aip CDKN2A interacting protein decreases expression ISO withaferin A results in decreased expression of CDKN2AIP protein CTD PMID:22973447 NCBI chr16:44,536,147...44,546,216
Ensembl chr16:44,536,234...44,540,033 		JBrowse link
G Cldn1 claudin 1 decreases response to substance
decreases expression		 ISO CLDN1 protein results in decreased susceptibility to withaferin A
withaferin A results in decreased expression of CLDN1 mRNA; withaferin A results in decreased expression of CLDN1 protein		 CTD PMID:33665778 NCBI chr11:74,421,569...74,436,728
Ensembl chr11:74,421,569...74,436,724 		JBrowse link
G Ddit3 DNA-damage inducible transcript 3 affects response to substance
multiple interactions
increases expression		 ISO DDIT3 mRNA affects the susceptibility to withaferin A
Acetylcysteine inhibits the reaction [withaferin A results in increased expression of DDIT3 protein]		 CTD PMID:21266191 NCBI chr 7:63,115,645...63,121,203
Ensembl chr 7:63,116,380...63,121,201 		JBrowse link
G Ddit4 DNA-damage-inducible transcript 4 multiple interactions
increases expression		 ISO Acetylcysteine inhibits the reaction [withaferin A results in increased expression of DDIT4 protein] CTD PMID:21266191 NCBI chr20:27,891,989...27,894,088
Ensembl chr20:27,891,998...27,894,105 		JBrowse link
G Dnmt1 DNA methyltransferase 1 decreases expression ISO withaferin A results in decreased expression of DNMT1 mRNA; withaferin A results in decreased expression of DNMT1 protein CTD PMID:23593078 NCBI chr 8:19,440,611...19,486,659
Ensembl chr 8:19,440,611...19,486,659 		JBrowse link
G Dnmt3a DNA methyltransferase 3 alpha decreases expression ISO withaferin A results in decreased expression of DNMT3A mRNA CTD PMID:23593078 NCBI chr 6:26,791,517...26,902,161
Ensembl chr 6:26,822,609...26,896,687 		JBrowse link
G Dnmt3b DNA methyltransferase 3 beta decreases expression ISO withaferin A results in decreased expression of DNMT3B mRNA CTD PMID:23593078 NCBI chr 3:142,130,592...142,169,124
Ensembl chr 3:142,130,592...142,169,124 		JBrowse link
G Edil3 EGF like repeats and discoidin domains 3 decreases expression ISO withaferin A results in decreased expression of EDIL3 mRNA CTD PMID:33665778 NCBI chr 2:19,890,396...20,405,028
Ensembl chr 2:19,890,373...20,405,008 		JBrowse link
G Eif2a eukaryotic translation initiation factor 2A increases phosphorylation ISO withaferin A results in increased phosphorylation of EIF2A protein CTD PMID:21266191 NCBI chr 2:142,761,303...142,794,767
Ensembl chr 2:142,761,416...142,795,068 		JBrowse link
G Ezr ezrin multiple interactions ISO [withanone co-treated with withaferin A] results in decreased expression of EZR protein CTD PMID:25236891 NCBI chr 1:46,967,961...47,011,505
Ensembl chr 1:46,967,658...47,011,505 		JBrowse link
G Fosl1 FOS like 1, AP-1 transcription factor subunit increases expression ISO withaferin A results in increased expression of FOSL1 mRNA CTD PMID:33665778 NCBI chr 1:202,754,549...202,763,057
Ensembl chr 1:202,754,529...202,764,930 		JBrowse link
G Hdac1 histone deacetylase 1 decreases expression ISO withaferin A results in decreased expression of HDAC1 protein CTD PMID:23593078 NCBI chr 5:141,853,992...141,881,057
Ensembl chr 5:141,853,989...141,881,111 		JBrowse link
G Hnrnpk heterogeneous nuclear ribonucleoprotein K multiple interactions ISO [withanone co-treated with withaferin A] results in decreased expression of HNRNPK protein; withaferin A binds to and results in decreased activity of HNRNPK protein CTD PMID:25236891 NCBI chr17:6,262,936...6,275,001
Ensembl chr17:6,262,998...6,274,997 		JBrowse link
G Hspa9 heat shock protein family A (Hsp70) member 9 affects binding
multiple interactions		 ISO withaferin A binds to HSPA9 protein
[withaferin A inhibits the reaction [HSPA9 protein binds to TP53 protein]] which affects the localization of and results in increased activity of TP53 protein; [withanone co-treated with withaferin A] results in decreased expression of HSPA9 protein; withaferin A inhibits the reaction [HSPA9 protein binds to TP53 protein]		 CTD PMID:22973447 PMID:25236891 NCBI chr18:26,536,131...26,554,294
Ensembl chr18:26,535,798...26,554,292 		JBrowse link
G Il1b interleukin 1 beta multiple interactions ISO withaferin A inhibits the reaction [IL1B protein promotes the reaction [ADAM17 protein results in increased cleavage of PROCR protein]] CTD PMID:24632454 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 withaferin A inhibits the reaction [Tetradecanoylphorbol Acetate results in increased expression of IL6 mRNA]; withaferin A inhibits the reaction [Tetradecanoylphorbol Acetate results in increased secretion of IL6 protein] CTD PMID:20438634 NCBI chr 4:5,214,602...5,219,178
Ensembl chr 4:5,213,394...5,219,178 		JBrowse link
G Krt13 keratin 13 decreases expression ISO withaferin A results in decreased expression of KRT13 mRNA CTD PMID:33665778 NCBI chr10:85,052,122...85,056,032
Ensembl chr10:85,051,889...85,056,084 		JBrowse link
G Mapk1 mitogen activated protein kinase 1 multiple interactions
increases phosphorylation		 ISO 2-(2-amino-3-methoxyphenyl)-4H-1-benzopyran-4-one inhibits the reaction [withaferin A results in increased phosphorylation of MAPK1 protein]; [withanone co-treated with withaferin A] results in decreased expression of MAPK1 protein; Acetylcysteine inhibits the reaction [withaferin A results in increased phosphorylation of MAPK1 protein]; SOD2 protein inhibits the reaction [withaferin A results in increased phosphorylation of MAPK1 protein]; withaferin A inhibits the reaction [Tetradecanoylphorbol Acetate results in increased phosphorylation of MAPK1 protein] CTD PMID:24019090 PMID:24632454 PMID:25236891 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 multiple interactions
increases phosphorylation		 ISO 2-(2-amino-3-methoxyphenyl)-4H-1-benzopyran-4-one inhibits the reaction [withaferin A results in increased phosphorylation of MAPK3 protein]; [withanone co-treated with withaferin A] results in decreased expression of MAPK3 protein; Acetylcysteine inhibits the reaction [withaferin A results in increased phosphorylation of MAPK3 protein]; SOD2 protein inhibits the reaction [withaferin A results in increased phosphorylation of MAPK3 protein]; withaferin A inhibits the reaction [Tetradecanoylphorbol Acetate results in increased phosphorylation of MAPK3 protein] CTD PMID:24019090 PMID:24632454 PMID:25236891 NCBI chr 1:181,366,646...181,372,863
Ensembl chr 1:181,366,637...181,372,863 		JBrowse link
G Mapk8 mitogen-activated protein kinase 8 increases phosphorylation ISO withaferin A results in increased phosphorylation of MAPK8 protein CTD PMID:21964475 NCBI chr16:8,638,897...8,721,960
Ensembl chr16:8,638,924...8,721,981 		JBrowse link
G Mcl1 MCL1 apoptosis regulator, BCL2 family member multiple interactions
increases expression		 ISO MCL1 mutant form promotes the reaction [withaferin A results in increased cleavage of PARP1 protein]
withaferin A results in increased expression of MCL1 protein		 CTD PMID:24019090 NCBI chr 2:183,219,137...183,235,676
Ensembl chr 2:183,219,220...183,222,303 		JBrowse link
G Mecp2 methyl CpG binding protein 2 decreases expression ISO withaferin A results in decreased expression of MECP2 protein CTD PMID:23593078 NCBI chr  X:151,781,177...151,844,687
Ensembl chr  X:151,789,930...151,844,689 		JBrowse link
G Mettl7a methyltransferase like 7A decreases expression ISO withaferin A results in decreased expression of METTL7A mRNA CTD PMID:33665778 NCBI chr 7:131,452,099...131,460,154
Ensembl chr 7:131,451,641...131,460,154 		JBrowse link
G Mmp2 matrix metallopeptidase 2 multiple interactions ISO [withanone co-treated with withaferin A] results in decreased expression of MMP2 protein CTD PMID:25236891 NCBI chr19:14,154,657...14,182,870
Ensembl chr19:14,154,657...14,182,870 		JBrowse link
G Nfe2l2 nuclear factor, erythroid 2-like 2 affects binding ISO withaferin A binds to NFE2L2 protein CTD PMID:22973447 NCBI chr 3:60,594,239...60,621,785
Ensembl chr 3:60,594,242...60,621,737 		JBrowse link
G Nfkbia NFKB inhibitor alpha multiple interactions ISO withaferin A inhibits the reaction [Tetradecanoylphorbol Acetate results in increased degradation of NFKBIA protein] CTD PMID:20438634 NCBI chr 6:72,858,713...72,861,941
Ensembl chr 6:72,858,712...72,861,941 		JBrowse link
G Nt5e 5' nucleotidase, ecto increases expression ISO withaferin A results in increased expression of NT5E mRNA CTD PMID:33665778 NCBI chr 8:89,271,046...89,314,918
Ensembl chr 8:89,270,696...89,314,881 		JBrowse link
G Parp1 poly (ADP-ribose) polymerase 1 multiple interactions
increases cleavage		 ISO Dithiothreitol inhibits the reaction [withaferin A results in increased cleavage of PARP1 protein]; MCL1 mutant form promotes the reaction [withaferin A results in increased cleavage of PARP1 protein] CTD PMID:20438634 PMID:24019090 NCBI chr13:92,307,593...92,339,406
Ensembl chr13:92,307,586...92,339,404 		JBrowse link
G Procr protein C receptor multiple interactions ISO withaferin A inhibits the reaction [IL1B protein promotes the reaction [ADAM17 protein results in increased cleavage of PROCR protein]]; withaferin A inhibits the reaction [Tetradecanoylphorbol Acetate promotes the reaction [ADAM17 protein results in increased cleavage of PROCR protein]]; withaferin A inhibits the reaction [TNF protein promotes the reaction [ADAM17 protein results in increased cleavage of PROCR protein]] CTD PMID:24632454 NCBI chr 3:144,254,596...144,258,863
Ensembl chr 3:144,254,380...144,258,903 		JBrowse link
G Ptgs2 prostaglandin-endoperoxide synthase 2 multiple interactions ISO withaferin A inhibits the reaction [[Lipopolysaccharides results in increased expression of PTGS2 protein] which results in increased chemical synthesis of Dinoprostone]; withaferin A inhibits the reaction [Lipopolysaccharides results in increased expression of PTGS2 mRNA] CTD PMID:21396905 NCBI chr13:62,164,080...62,169,770
Ensembl chr13:62,163,932...62,172,188 		JBrowse link
G Rela RELA proto-oncogene, NF-kB subunit multiple interactions ISO withaferin A inhibits the reaction [Tetradecanoylphorbol Acetate results in increased phosphorylation of RELA protein] CTD PMID:20438634 NCBI chr 1:202,925,001...202,935,484
Ensembl chr 1:202,924,945...202,935,484 		JBrowse link
G Slco4a1 solute carrier organic anion transporter family, member 4a1 increases expression ISO withaferin A results in increased expression of SLCO4A1 mRNA CTD PMID:33665778 NCBI chr 3:167,559,177...167,578,307
Ensembl chr 3:167,559,316...167,578,305 		JBrowse link
G Sod2 superoxide dismutase 2 multiple interactions ISO SOD2 protein inhibits the reaction [withaferin A results in increased phosphorylation of MAPK1 protein]; SOD2 protein inhibits the reaction [withaferin A results in increased phosphorylation of MAPK3 protein] CTD PMID:24019090 NCBI chr 1:47,638,318...47,645,163
Ensembl chr 1:47,636,528...47,645,189 		JBrowse link
G Stat1 signal transducer and activator of transcription 1 multiple interactions ISO withaferin A inhibits the reaction [Lipopolysaccharides results in increased phosphorylation of and results in increased localization of and results in increased activity of STAT1 protein] CTD PMID:21396905 NCBI chr 9:49,419,561...49,459,969 JBrowse link
G Stat3 signal transducer and activator of transcription 3 multiple interactions ISO withaferin A inhibits the reaction [Lipopolysaccharides results in increased phosphorylation of and results in increased activity of STAT3 protein] CTD PMID:21396905 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
decreases activity		 ISO withaferin A inhibits the reaction [TNF protein promotes the reaction [ADAM17 protein results in increased cleavage of PROCR protein]]
withaferin A results in decreased activity of TNF protein		 CTD PMID:20438634 PMID:24632454 NCBI chr20:3,622,011...3,624,629
Ensembl chr20:3,622,011...3,624,629 		JBrowse link
G Tnfaip3 TNF alpha induced protein 3 multiple interactions ISO withaferin A inhibits the reaction [Tetradecanoylphorbol Acetate results in increased expression of TNFAIP3 mRNA] CTD PMID:20438634 NCBI chr 1:13,709,211...13,724,291
Ensembl chr 1:13,709,206...13,725,282 		JBrowse link
G Tp53 tumor protein p53 increases expression
affects binding
multiple interactions		 ISO withaferin A results in increased expression of TP53 mRNA
withaferin A binds to TP53 protein
[withaferin A inhibits the reaction [HSPA9 protein binds to TP53 protein]] which affects the localization of and results in increased activity of TP53 protein; withaferin A inhibits the reaction [HSPA9 protein binds to TP53 protein]		 CTD PMID:22973447 NCBI chr10:54,300,070...54,311,525
Ensembl chr10:54,300,048...54,311,524 		JBrowse link
G Tuba1a tubulin, alpha 1A decreases expression ISO withaferin A results in decreased expression of TUBA1A mRNA CTD PMID:24297176 NCBI chr 7:130,113,214...130,116,880 JBrowse link
G Tubb5 tubulin, beta 5 class I decreases expression ISO withaferin A results in decreased expression of TUBB mRNA CTD PMID:24297176 NCBI chr20:2,912,779...2,916,928
Ensembl chr20:2,912,778...2,916,940 		JBrowse link
G Vegfa vascular endothelial growth factor A multiple interactions
decreases expression		 ISO [withanone co-treated with withaferin A] results in decreased secretion of VEGFA protein; withaferin A inhibits the reaction [Tetradecanoylphorbol Acetate results in increased expression of VEGFA mRNA]
withaferin A results in decreased expression of VEGFA protein		 CTD PMID:20438634 PMID:25236891 NCBI chr 9:14,955,300...14,970,641
Ensembl chr 9:14,955,300...14,970,641 		JBrowse link
G Xbp1 X-box binding protein 1 increases expression
increases splicing		 ISO withaferin A results in increased expression of XBP1 protein
withaferin A results in increased splicing of XBP1 mRNA		 CTD PMID:21266191 NCBI chr14:80,390,629...80,395,713
Ensembl chr14:80,390,643...80,395,693 		JBrowse link
Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19821
    role 19769
      biological role 19769
        biochemical role 19389
          apoptosis inducer 13236
            withaferin A 52
              2,3-dihydro-3beta-O-sulfate withaferin A 0
              2,3-dihydro-3beta-methoxy withaferin A 0
              2,3-dihydrowithaferin A 0
              sitoindoside IX 0
              withalongolide A 0
              withalongolide B 0
              withalongolide C 0
              withalongolide G 0
              withalongolide H 0
Path 2
Term Annotations click to browse term
  CHEBI ontology 19821
    subatomic particle 19819
      composite particle 19819
        hadron 19819
          baryon 19819
            nucleon 19819
              atomic nucleus 19819
                atom 19819
                  main group element atom 19716
                    p-block element atom 19716
                      carbon group element atom 19640
                        carbon atom 19630
                          organic molecular entity 19630
                            organic group 18737
                              organic divalent group 18728
                                organodiyl group 18728
                                  carbonyl group 18675
                                    carbonyl compound 18675
                                      carboxylic ester 15884
                                        lactone 11242
                                          steroid lactone 417
                                            withanolide 52
                                              withaferin A 52
                                                2,3-dihydro-3beta-O-sulfate withaferin A 0
                                                2,3-dihydro-3beta-methoxy withaferin A 0
                                                2,3-dihydrowithaferin A 0
                                                sitoindoside IX 0
                                                withalongolide A 0
                                                withalongolide B 0
                                                withalongolide C 0
                                                withalongolide G 0
                                                withalongolide H 0
paths to the root