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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:bufalin
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Accession:CHEBI:517248 term browser browse the term
Definition:A 14beta-hydroxy steroid that is bufan-20,22-dienolide having hydroxy substituents at the 5beta- and 14beta-positions. It has been isolated from the skin of the toad Bufo bufo.
Synonyms:exact_synonym: (3beta,5beta)-3,14-dihydroxybufa-20,22-dienolide
 related_synonym: 3,14-Dihydroxy-bufa-20,22-dienolide;   3-beta,14-Dihydroxy-5-beta-bufa-20,22-dienolide;   3beta,14beta-dihydroxy-5beta-bufa-20,22-dienolide;   Formula=C24H34O4;   InChI=1S/C24H34O4/c1-22-10-7-17(25)13-16(22)4-5-20-19(22)8-11-23(2)18(9-12-24(20,23)27)15-3-6-21(26)28-14-15/h3,6,14,16-20,25,27H,4-5,7-13H2,1-2H3/t16-,17+,18-,19+,20-,22+,23-,24+/m1/s1;   InChIKey=QEEBRPGZBVVINN-BMPKRDENSA-N;   SMILES=[H][C@]12CC[C@]3([H])[C@]([H])(CC[C@]4(C)[C@]([H])(CC[C@]34O)c3ccc(=O)oc3)[C@@]1(C)CC[C@H](O)C2
 xref: Beilstein:96550;   CAS:465-21-4;   KEGG:C16922;   LIPID_MAPS_instance:LMST01130001
 xref_mesh: MESH:C022777
 xref: PMID:10438974;   PMID:21185919;   PMID:23949904;   PMID:24484199;   PMID:24515724;   PMID:24719521;   PMID:26111756;   PMID:26133118;   PMID:26381511;   PMID:26446205;   PMID:8282340;   Reaxys:96550


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bufalin 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 bufalin inhibits the reaction [ABCB1 protein results in increased transport of quinidinium] CTD PMID:23104431 NCBI chr 4:25,357,467...25,529,941
Ensembl chr 4:25,158,362...25,442,709 		JBrowse link
G Actb actin, beta increases expression ISO bufalin results in increased expression of ACTB protein CTD PMID:23091618 NCBI chr12:11,663,112...11,666,697
Ensembl chr12:11,663,109...11,672,877 		JBrowse link
G Actg1 actin, gamma 1 increases expression ISO bufalin results in increased expression of ACTG1 protein CTD PMID:23091618 NCBI chr10:105,619,738...105,622,587
Ensembl chr10:105,619,737...105,624,232 		JBrowse link
G Akt1 AKT serine/threonine kinase 1 multiple interactions ISO bufalin results in increased phosphorylation of and results in decreased expression of AKT1 protein CTD PMID:23949904 NCBI chr 6:131,713,716...131,735,319
Ensembl chr 6:131,713,720...131,733,921 		JBrowse link
G Apaf1 apoptotic peptidase activating factor 1 increases expression ISO bufalin results in increased expression of APAF1 protein CTD PMID:27444971 NCBI chr 7:25,494,143...25,579,540
Ensembl chr 7:25,494,609...25,579,540 		JBrowse link
G Bcl2 BCL2, apoptosis regulator decreases expression ISO bufalin results in decreased expression of BCL2 mRNA; bufalin results in decreased expression of BCL2 protein CTD PMID:7658701 PMID:27444971 NCBI chr13:22,689,783...22,853,920
Ensembl chr13:22,684,989...22,853,743
Ensembl chr13:22,684,989...22,853,743 		JBrowse link
G Casp3 caspase 3 increases expression ISO bufalin results in increased expression of CASP3 mRNA; bufalin results in increased expression of CASP3 protein modified form CTD PMID:27444971 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 bufalin results in increased activity of CASP9 protein CTD PMID:27444971 NCBI chr 5:154,108,872...154,126,628
Ensembl chr 5:154,109,046...154,126,626 		JBrowse link
G Cope COPI coat complex subunit epsilon decreases expression ISO bufalin results in decreased expression of COPE protein CTD PMID:23091618 NCBI chr16:19,114,871...19,125,527
Ensembl chr16:19,114,871...19,128,907 		JBrowse link
G Cycs cytochrome c, somatic multiple interactions
increases expression		 ISO bufalin inhibits the reaction [HSPB1 protein binds to CYCS protein]; HSPB1 protein inhibits the reaction [bufalin inhibits the reaction [HSPB1 protein binds to CYCS protein]]
bufalin results in increased expression of CYCS protein		 CTD PMID:23091618 PMID:27444971 NCBI chr 4:79,651,894...79,653,994
Ensembl chr 4:79,651,378...79,654,054 		JBrowse link
G Cyp3a2 cytochrome P450, family 3, subfamily a, polypeptide 2 increases metabolic processing
increases expression
multiple interactions		 ISO CYP3A4 protein results in increased metabolism of bufalin
bufalin results in increased expression of CYP3A4 mRNA
bufalin promotes the reaction [CYP3A4 protein results in increased metabolism of Midazolam]; bufalin results in increased expression of and results in increased activity of CYP3A4 protein; Ketoconazole inhibits the reaction [CYP3A4 protein results in increased metabolism of bufalin]		 CTD PMID:22178124 NCBI chr12:9,207,986...9,230,038
Ensembl chr12:9,015,383...9,285,008 		JBrowse link
G Ddit3 DNA-damage inducible transcript 3 increases expression ISO bufalin results in increased expression of DDIT3 mRNA CTD PMID:27444971 NCBI chr 7:63,115,645...63,121,203
Ensembl chr 7:63,116,380...63,121,201 		JBrowse link
G Dnajb11 DnaJ heat shock protein family (Hsp40) member B11 increases expression ISO bufalin results in increased expression of DNAJB11 protein CTD PMID:23091618 NCBI chr11:78,151,750...78,168,259
Ensembl chr11:78,150,429...78,180,407 		JBrowse link
G Dut deoxyuridine triphosphatase decreases expression ISO bufalin results in decreased expression of DUT protein CTD PMID:23091618 NCBI chr 3:112,498,864...112,509,994
Ensembl chr 3:112,498,982...112,510,771 		JBrowse link
G Eif2ak3 eukaryotic translation initiation factor 2 alpha kinase 3 decreases phosphorylation ISO bufalin results in decreased phosphorylation of EIF2AK3 protein CTD PMID:23949904 NCBI chr 4:102,805,495...102,866,914
Ensembl chr 4:102,805,510...102,866,911 		JBrowse link
G Endog endonuclease G increases expression ISO bufalin results in increased expression of ENDOG mRNA; bufalin results in increased expression of ENDOG protein CTD PMID:27444971 NCBI chr 3:13,449,113...13,451,715
Ensembl chr 3:13,449,086...13,451,932 		JBrowse link
G Eno1 enolase 1 decreases expression ISO bufalin results in decreased expression of ENO1 protein CTD PMID:23091618 NCBI chr 5:160,719,951...160,731,337
Ensembl chr 5:160,719,951...160,731,336 		JBrowse link
G Fas Fas cell surface death receptor increases expression ISO bufalin results in increased expression of FAS protein CTD PMID:27444971 NCBI chr 1:231,798,963...231,832,591
Ensembl chr 1:231,798,960...231,832,591 		JBrowse link
G Faslg Fas ligand increases expression ISO bufalin results in increased expression of FASLG protein CTD PMID:27444971 NCBI chr13:74,151,519...74,172,760
Ensembl chr13:74,154,954...74,162,215 		JBrowse link
G Fos Fos proto-oncogene, AP-1 transcription factor subunit multiple interactions
increases expression		 ISO 2-(2-(4-(4-nitrobenzyloxy)phenyl)ethyl)isothiourea methanesulfonate inhibits the reaction [bufalin results in increased expression of FOS mRNA]; 2-(2-amino-3-methoxyphenyl)-4H-1-benzopyran-4-one inhibits the reaction [bufalin results in increased expression of FOS mRNA] CTD PMID:10712238 NCBI chr 6:105,121,170...105,124,036
Ensembl chr 6:105,121,170...105,124,036 		JBrowse link
G Grb2 growth factor receptor bound protein 2 decreases expression ISO bufalin results in decreased expression of GRB2 protein CTD PMID:23949904 NCBI chr10:100,881,404...100,949,193
Ensembl chr10:100,869,718...100,949,309 		JBrowse link
G Gstp1 glutathione S-transferase pi 1 decreases expression ISO bufalin results in decreased expression of GSTP1 protein CTD PMID:23091618 NCBI chr 1:201,337,762...201,340,230
Ensembl chr 1:201,321,672...201,340,226 		JBrowse link
G Hnrnph1 heterogeneous nuclear ribonucleoprotein H1 decreases expression ISO bufalin results in decreased expression of HNRNPH1 protein CTD PMID:23091618 NCBI chr10:34,692,868...34,702,849
Ensembl chr10:34,693,555...34,702,846 		JBrowse link
G Hnrnpk heterogeneous nuclear ribonucleoprotein K decreases expression ISO bufalin results in decreased expression of HNRNPK protein CTD PMID:23091618 NCBI chr17:6,262,936...6,275,001
Ensembl chr17:6,262,998...6,274,997 		JBrowse link
G Hspa5 heat shock protein family A (Hsp70) member 5 decreases expression ISO bufalin results in decreased expression of HSPA5 mRNA CTD PMID:27444971 NCBI chr 3:18,055,507...18,059,969
Ensembl chr 3:18,055,405...18,059,891 		JBrowse link
G Hspb1 heat shock protein family B (small) member 1 multiple interactions
decreases expression
decreases response to substance		 ISO benzyloxycarbonylleucyl-leucyl-leucine aldehyde inhibits the reaction [bufalin results in decreased expression of HSPB1 protein]; bufalin inhibits the reaction [HSPB1 protein binds to CYCS protein]; HSPB1 protein inhibits the reaction [bufalin affects the localization of RELA protein]; HSPB1 protein inhibits the reaction [bufalin inhibits the reaction [HSPB1 protein binds to CYCS protein]]; HSPB1 protein inhibits the reaction [bufalin results in increased cleavage of PARP1 protein]
HSPB1 protein results in decreased susceptibility to bufalin		 CTD PMID:23091618 NCBI chr12:20,794,014...20,795,675
Ensembl chr12:20,794,028...20,795,743 		JBrowse link
G Il1b interleukin 1 beta multiple interactions
increases expression		 ISO 2-(2-(4-(4-nitrobenzyloxy)phenyl)ethyl)isothiourea methanesulfonate inhibits the reaction [bufalin results in increased expression of IL1B mRNA]; 2-(2-amino-3-methoxyphenyl)-4H-1-benzopyran-4-one inhibits the reaction [bufalin results in increased expression of IL1B mRNA]; Ro 31-8220 inhibits the reaction [bufalin results in increased expression of IL1B mRNA]; SB 203580 promotes the reaction [bufalin results in increased expression of IL1B mRNA] CTD PMID:10712238 NCBI chr 3:116,577,005...116,583,386
Ensembl chr 3:116,577,010...116,583,415 		JBrowse link
G Jun Jun proto-oncogene, AP-1 transcription factor subunit decreases phosphorylation ISO bufalin results in decreased phosphorylation of JUN protein CTD PMID:23949904 NCBI chr 5:109,894,175...109,897,268
Ensembl chr 5:109,893,145...109,897,656 		JBrowse link
G Krt18 keratin 18 increases expression ISO bufalin results in increased expression of KRT18 protein CTD PMID:23091618 NCBI chr 7:133,157,486...133,161,162
Ensembl chr 7:133,157,475...133,161,166 		JBrowse link
G Map2k7 mitogen activated protein kinase kinase 7 decreases expression ISO bufalin results in decreased expression of MAP2K7 protein CTD PMID:23949904 NCBI chr12:2,591,312...2,604,211
Ensembl chr12:2,591,219...2,604,222 		JBrowse link
G Map3k3 mitogen activated protein kinase kinase kinase 3 decreases expression ISO bufalin results in decreased expression of MAP3K3 protein CTD PMID:23949904 NCBI chr10:91,020,174...91,088,852
Ensembl chr10:91,020,174...91,088,848 		JBrowse link
G Mapk1 mitogen activated protein kinase 1 multiple interactions
increases phosphorylation
decreases activity		 ISO 2-(2-(4-(4-nitrobenzyloxy)phenyl)ethyl)isothiourea methanesulfonate inhibits the reaction [bufalin results in increased phosphorylation of MAPK1 protein]; Ro 31-8220 inhibits the reaction [bufalin results in increased phosphorylation of MAPK1 protein]; SB 203580 promotes the reaction [bufalin results in increased phosphorylation of MAPK1 protein]
bufalin results in decreased activity of MAPK1 protein		 CTD PMID:10712238 PMID:21922632 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
decreases activity		 ISO 2-(2-(4-(4-nitrobenzyloxy)phenyl)ethyl)isothiourea methanesulfonate inhibits the reaction [bufalin results in increased phosphorylation of MAPK3 protein]; Ro 31-8220 inhibits the reaction [bufalin results in increased phosphorylation of MAPK3 protein]; SB 203580 promotes the reaction [bufalin results in increased phosphorylation of MAPK3 protein]
bufalin results in decreased activity of MAPK3 protein		 CTD PMID:10712238 PMID:21922632 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 decreases activity ISO bufalin results in decreased activity of MAPK8 protein CTD PMID:21922632 NCBI chr16:8,638,897...8,721,960
Ensembl chr16:8,638,924...8,721,981 		JBrowse link
G Mapk9 mitogen-activated protein kinase 9 decreases activity ISO bufalin results in decreased activity of MAPK9 protein CTD PMID:21922632 NCBI chr10:34,169,661...34,211,138
Ensembl chr10:34,169,675...34,210,178 		JBrowse link
G Mcl1 MCL1 apoptosis regulator, BCL2 family member decreases expression ISO bufalin co-treated with osimertinib decreases expression of MCL1 protein in lung
Bufalin decreases expression of MCL1 protein in lung		 RGD PMID:31301315 PMID:28419994 RGD:151356917, RGD:151356918 NCBI chr 2:183,219,137...183,235,676
Ensembl chr 2:183,219,220...183,222,303 		JBrowse link
G Mmp1 matrix metallopeptidase 1 decreases expression ISO bufalin results in decreased expression of MMP1 protein CTD PMID:23949904 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
decreases secretion		 ISO bufalin results in decreased expression of and results in decreased activity of MMP2 protein
bufalin results in decreased expression of MMP2 mRNA
bufalin results in decreased secretion of MMP2 protein		 CTD PMID:21922632 PMID:23949904 NCBI chr19:14,154,657...14,182,870
Ensembl chr19:14,154,657...14,182,870 		JBrowse link
G Mmp9 matrix metallopeptidase 9 decreases activity
decreases expression
multiple interactions
decreases secretion		 ISO bufalin results in decreased activity of MMP9 protein
bufalin results in decreased expression of MMP9 mRNA
bufalin results in decreased expression of and results in decreased activity of MMP9 protein
bufalin results in decreased secretion of MMP9 protein		 CTD PMID:21922632 PMID:23949904 NCBI chr 3:153,684,158...153,692,118
Ensembl chr 3:153,683,858...153,692,120 		JBrowse link
G Myc MYC proto-oncogene, bHLH transcription factor decreases expression ISO bufalin results in decreased expression of MYC mRNA CTD PMID:7658701 NCBI chr 7:93,593,705...93,598,633
Ensembl chr 7:93,593,705...93,598,630 		JBrowse link
G Nos2 nitric oxide synthase 2 decreases expression ISO bufalin results in decreased expression of NOS2 protein CTD PMID:23949904 NCBI chr10:63,815,308...63,851,208
Ensembl chr10:63,815,308...63,851,210 		JBrowse link
G Parp1 poly (ADP-ribose) polymerase 1 increases cleavage
multiple interactions		 ISO bufalin results in increased cleavage of PARP1 protein
HSPB1 protein inhibits the reaction [bufalin results in increased cleavage of PARP1 protein]		 CTD PMID:23091618 NCBI chr13:92,307,593...92,339,406
Ensembl chr13:92,307,586...92,339,404 		JBrowse link
G Ppa1 inorganic pyrophosphatase 1 decreases expression ISO bufalin results in decreased expression of PPA1 protein CTD PMID:23091618 NCBI chr20:29,590,733...29,617,711
Ensembl chr20:29,590,707...29,619,215 		JBrowse link
G Ppp2cb protein phosphatase 2 catalytic subunit beta decreases expression ISO bufalin results in decreased expression of PPP2CB protein CTD PMID:23091618 NCBI chr16:58,558,119...58,579,325
Ensembl chr16:58,558,122...58,579,576 		JBrowse link
G Psma3 proteasome 20S subunit alpha 3 decreases expression ISO bufalin results in decreased expression of PSMA3 protein CTD PMID:23091618 NCBI chr 6:89,483,741...89,503,775
Ensembl chr 6:89,483,727...89,504,965 		JBrowse link
G Ptgs2 prostaglandin-endoperoxide synthase 2 decreases expression ISO bufalin results in decreased expression of PTGS2 protein CTD PMID:23949904 NCBI chr13:62,164,080...62,169,770
Ensembl chr13:62,163,932...62,172,188 		JBrowse link
G Ptk2 protein tyrosine kinase 2 decreases expression ISO bufalin results in decreased expression of PTK2 protein CTD PMID:23949904 NCBI chr 7:105,126,725...105,331,848
Ensembl chr 7:105,126,728...105,331,783 		JBrowse link
G Rela RELA proto-oncogene, NF-kB subunit decreases expression
affects localization
multiple interactions		 ISO bufalin results in decreased expression of RELA protein
bufalin affects the localization of RELA protein
HSPB1 protein inhibits the reaction [bufalin affects the localization of RELA protein]		 CTD PMID:23091618 PMID:23949904 NCBI chr 1:202,925,001...202,935,484
Ensembl chr 1:202,924,945...202,935,484 		JBrowse link
G Rhoa ras homolog family member A decreases expression ISO bufalin results in decreased expression of RHOA protein CTD PMID:23949904 NCBI chr 8:108,991,926...109,025,746
Ensembl chr 8:108,991,954...109,025,746 		JBrowse link
G Rock1 Rho-associated coiled-coil containing protein kinase 1 decreases expression ISO bufalin results in decreased expression of ROCK1 protein CTD PMID:23949904 NCBI chr18:1,114,532...1,236,345
Ensembl chr18:1,115,905...1,235,571 		JBrowse link
G Rplp0 ribosomal protein lateral stalk subunit P0 decreases expression ISO bufalin results in decreased expression of RPLP0 protein CTD PMID:23091618 NCBI chr12:41,054,363...41,057,632
Ensembl chr12:41,054,179...41,057,632 		JBrowse link
G Rpsa ribosomal protein SA increases expression ISO bufalin results in increased expression of RPSA protein CTD PMID:23091618 NCBI chr 8:119,851,225...119,855,103
Ensembl chr 8:119,851,225...119,855,247 		JBrowse link
G Sarnp SAP domain containing ribonucleoprotein increases expression ISO bufalin results in increased expression of SARNP protein CTD PMID:23091618 NCBI chr 7:1,251,096...1,305,335
Ensembl chr 7:1,251,098...1,305,332 		JBrowse link
G Sos1 SOS Ras/Rac guanine nucleotide exchange factor 1 decreases expression ISO bufalin results in decreased expression of SOS1 protein CTD PMID:23949904 NCBI chr 6:14,533,870...14,613,348
Ensembl chr 6:14,533,360...14,611,107 		JBrowse link
G Tardbp TAR DNA binding protein decreases expression ISO bufalin results in decreased expression of TARDBP protein CTD PMID:23091618 NCBI chr 5:159,050,518...159,062,218
Ensembl chr 5:159,051,799...159,062,055 		JBrowse link
G Tcp1 t-complex 1 decreases expression ISO bufalin results in decreased expression of TCP1 protein CTD PMID:23091618 NCBI chr 1:47,829,061...47,836,809
Ensembl chr 1:47,828,652...47,836,839 		JBrowse link
G Tmod3 tropomodulin 3 decreases expression ISO bufalin results in decreased expression of TMOD3 protein CTD PMID:23091618 NCBI chr 8:76,248,978...76,310,855
Ensembl chr 8:76,248,979...76,310,977 		JBrowse link
G Tnf tumor necrosis factor increases expression
multiple interactions		 ISO bufalin results in increased expression of TNF mRNA
SB 203580 promotes the reaction [bufalin results in increased expression of TNF mRNA]		 CTD PMID:10712238 NCBI chr20:3,622,011...3,624,629
Ensembl chr20:3,622,011...3,624,629 		JBrowse link
G Tpi1 triosephosphate isomerase 1 decreases expression ISO bufalin results in decreased expression of TPI1 protein CTD PMID:23091618 NCBI chr 4:157,615,283...157,618,813
Ensembl chr 4:157,615,386...157,619,541 		JBrowse link
G Tpt1 tumor protein, translationally-controlled 1 decreases expression ISO bufalin results in decreased expression of TPT1 protein CTD PMID:23091618 NCBI chr15:51,156,728...51,159,629
Ensembl chr15:51,146,154...51,159,625 		JBrowse link
G Vegfa vascular endothelial growth factor A decreases expression ISO bufalin results in decreased expression of VEGFA protein CTD PMID:23949904 NCBI chr 9:14,955,300...14,970,641
Ensembl chr 9:14,955,300...14,970,641 		JBrowse link
Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19812
    role 19784
      application 19615
        anti-inflammatory agent 16506
          bufalin 61
Path 2
Term Annotations click to browse term
  CHEBI ontology 19812
    subatomic particle 19810
      composite particle 19810
        hadron 19810
          baryon 19810
            nucleon 19810
              atomic nucleus 19810
                atom 19810
                  main group element atom 19755
                    p-block element atom 19755
                      carbon group element atom 19698
                        carbon atom 19693
                          organic molecular entity 19693
                            organic group 18902
                              organic divalent group 18884
                                organodiyl group 18884
                                  carbonyl group 18850
                                    carbonyl compound 18850
                                      carboxylic ester 16000
                                        lactone 11444
                                          steroid lactone 454
                                            bufanolide 100
                                              bufalin 61
paths to the root