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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:(-)-gambogic acid
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Accession:CHEBI:67521 term browser browse the term
Definition:A pyranoxanthone that has formula C38H44O8.
Synonyms:related_synonym: (2Z)-4-[(1S,2S,8R,17S,19R)-12-Hydroxy-8,21,21-trimethyl-5-(3-methyl-2-buten-1-yl)-8-(4-methyl-3-penten-1-yl)-14,18-dioxo-3,7,20-trioxahexacyclo[15.4.1.0[2,15].0[2,19].0[4,13].0[6,11]]docosa-4(13),5,9, 11,15-pentaen-19-yl]-2-methyl-2-butenoic acid;   Formula=C38H44O8;   Guttic acid;   InChI=1S/C38H44O8/c1-20(2)10-9-15-36(8)16-14-24-29(39)28-30(40)26-18-23-19-27-35(6,7)46-37(33(23)41,17-13-22(5)34(42)43)38(26,27)45-32(28)25(31(24)44-36)12-11-21(3)4/h10-11,13-14,16,18,23,27,39H,9,12,15,17,19H2,1-8H3,(H,42,43)/b22-13-/t23-,27+,36-,37+,38-/m1/s1;   InChIKey=GEZHEQNLKAOMCA-RRZNCOCZSA-N;   SMILES=[H][C@@]12C[C@@]3([H])C(C)(C)O[C@@](CC=C(C)C(O)=O)(C1=O)[C@]31Oc3c(CC=C(C)C)c4O[C@](C)(CCC=C(C)C)C=Cc4c(O)c3C(=O)C1=C2;   beta-Guttiferin
 xref: CAS:2752-65-0;   KEGG:C10062;   KNApSAcK:C00002950
 xref_mesh: MESH:C052659
 xref: PMID:21486005


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(-)-gambogic acid 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 [gambogic acid affects the reaction [ABCB1 protein affects the susceptibility to Doxorubicin]] which affects the cleavage of CASP7 protein; [gambogic acid affects the reaction [ABCB1 protein affects the susceptibility to Doxorubicin]] which affects the cleavage of PARP1 protein; Acetylcysteine affects the reaction [[gambogic acid affects the reaction [ABCB1 protein affects the susceptibility to Doxorubicin]] which affects the cleavage of CASP7 protein]; Acetylcysteine affects the reaction [[gambogic acid affects the reaction [ABCB1 protein affects the susceptibility to Doxorubicin]] which affects the cleavage of PARP1 protein]; gambogic acid affects the reaction [ABCB1 protein affects the susceptibility to Doxorubicin] CTD PMID:25824409 NCBI chr 4:26,312,403...26,488,456
Ensembl chr 4:25,158,362...25,442,709 		JBrowse link
G Aifm1 apoptosis inducing factor, mitochondria associated 1 affects localization ISO gambogic acid affects the localization of AIFM1 protein CTD PMID:19464570 NCBI chr  X:127,650,223...127,689,356
Ensembl chr  X:127,650,226...127,689,256 		JBrowse link
G Akt1 AKT serine/threonine kinase 1 decreases activity
decreases expression 		ISO gambogic acid results in decreased activity of AKT1 protein
gambogic acid results in decreased expression of AKT1 mRNA 		CTD PMID:19433130 PMID:33533530 NCBI chr 6:137,534,810...137,555,131
Ensembl chr 6:131,713,720...131,733,921 		JBrowse link
G Akt2 AKT serine/threonine kinase 2 decreases expression ISO gambogic acid results in decreased expression of AKT2 mRNA CTD PMID:33533530 NCBI chr 1:92,004,705...92,061,420
Ensembl chr 1:82,883,547...82,933,817 		JBrowse link
G Bax BCL2 associated X, apoptosis regulator increases expression ISO gambogic acid results in increased expression of BAX mRNA CTD PMID:15968715 PMID:33533530 NCBI chr 1:105,076,472...105,081,906
Ensembl chr 1:95,938,808...95,945,368 		JBrowse link
G Bcl2 BCL2, apoptosis regulator affects expression
multiple interactions
decreases expression 		ISO gambogic acid affects the expression of BCL2 protein
[Verapamil co-treated with gambogic acid] results in decreased expression of BCL2 protein; Fluorouracil promotes the reaction [gambogic acid results in decreased expression of BCL2 mRNA] 		CTD PMID:15968715 PMID:19084572 PMID:19433130 PMID:24373880 PMID:33533530 NCBI chr13:23,204,464...23,366,900
Ensembl chr13:22,684,989...22,853,743
Ensembl chr13:22,684,989...22,853,743 		JBrowse link
G Birc5 baculoviral IAP repeat-containing 5 multiple interactions
affects expression 		ISO [gambogic acid co-treated with Doxorubicin] affects the expression of BIRC5 protein; SB 203580 affects the reaction [[gambogic acid co-treated with Doxorubicin] affects the expression of BIRC5 protein]
gambogic acid affects the expression of BIRC5 protein 		CTD PMID:25824409 NCBI chr10:103,567,369...103,580,069
Ensembl chr10:103,073,408...103,081,380 		JBrowse link
G Casp3 caspase 3 multiple interactions
decreases expression 		ISO [gambogic acid co-treated with Bortezomib] results in increased activity of CASP3 protein; [Verapamil co-treated with gambogic acid] results in increased cleavage of and results in increased activity of CASP3 protein; benzyloxycarbonyl-valyl-alanyl-aspartic acid analog inhibits the reaction [[gambogic acid co-treated with Bortezomib] results in increased activity of CASP3 protein]; Fluorouracil promotes the reaction [gambogic acid results in decreased expression of CASP3 mRNA] CTD PMID:19084572 PMID:24291039 PMID:24373880 NCBI chr16:52,395,539...52,413,794
Ensembl chr16:45,662,910...45,684,648 		JBrowse link
G Casp7 caspase 7 multiple interactions ISO [gambogic acid affects the reaction [ABCB1 protein affects the susceptibility to Doxorubicin]] which affects the cleavage of CASP7 protein; Acetylcysteine affects the reaction [[gambogic acid affects the reaction [ABCB1 protein affects the susceptibility to Doxorubicin]] which affects the cleavage of CASP7 protein] CTD PMID:25824409 NCBI chr 1:265,442,647...265,481,938
Ensembl chr 1:255,437,172...255,476,729 		JBrowse link
G Casp8 caspase 8 multiple interactions ISO [gambogic acid co-treated with Bortezomib] results in increased activity of CASP8 protein; [Verapamil co-treated with gambogic acid] results in increased cleavage of and results in increased activity of CASP8 protein CTD PMID:24291039 PMID:24373880 NCBI chr 9:67,747,109...67,806,699
Ensembl chr 9:60,264,075...60,312,542 		JBrowse link
G Casp9 caspase 9 decreases expression
multiple interactions 		ISO gambogic acid results in decreased expression of CASP9 protein alternative form
[gambogic acid co-treated with Bortezomib] results in increased activity of CASP9 protein; [Verapamil co-treated with gambogic acid] results in increased cleavage of and results in increased activity of CASP9 protein; benzyloxycarbonyl-valyl-alanyl-aspartic acid analog inhibits the reaction [[gambogic acid co-treated with Bortezomib] results in increased activity of CASP9 protein] 		CTD PMID:19464570 PMID:24291039 PMID:24373880 Ensembl chr 5:154,109,046...154,126,626 JBrowse link
G Ddit3 DNA-damage inducible transcript 3 multiple interactions
increases expression 		ISO [Verapamil co-treated with gambogic acid] results in increased expression of DDIT3 protein; Bortezomib promotes the reaction [gambogic acid results in increased expression of DDIT3 protein]; gambogic acid promotes the reaction [Bortezomib results in increased expression of DDIT3 protein] CTD PMID:24291039 PMID:24373880 NCBI chr 7:65,001,695...65,006,517
Ensembl chr 7:63,116,380...63,121,201 		JBrowse link
G Gsk3b glycogen synthase kinase 3 beta decreases activity ISO gambogic acid results in decreased activity of GSK3B protein CTD PMID:19433130 NCBI chr11:76,004,502...76,154,665
Ensembl chr11:62,504,316...62,648,646 		JBrowse link
G Hspa5 heat shock protein family A (Hsp70) member 5 multiple interactions
increases expression 		ISO Bortezomib promotes the reaction [gambogic acid results in increased expression of HSPA5 protein]; gambogic acid promotes the reaction [Bortezomib results in increased expression of HSPA5 protein] CTD PMID:24291039 NCBI chr 3:38,453,016...38,457,475
Ensembl chr 3:18,055,405...18,059,891 		JBrowse link
G Ncoa3 nuclear receptor coactivator 3 decreases expression ISO gambogic acid results in decreased expression of NCOA3 CTD PMID:19433130 NCBI chr 3:175,157,824...175,237,831
Ensembl chr 3:154,738,581...154,818,594 		JBrowse link
G Parp1 poly (ADP-ribose) polymerase 1 increases cleavage
decreases expression
multiple interactions 		ISO gambogic acid results in increased cleavage of PARP1 protein
gambogic acid results in decreased expression of PARP1 mRNA
[gambogic acid affects the reaction [ABCB1 protein affects the susceptibility to Doxorubicin]] which affects the cleavage of PARP1 protein; [Verapamil co-treated with gambogic acid] results in increased cleavage of PARP1 protein; Acetylcysteine affects the reaction [[gambogic acid affects the reaction [ABCB1 protein affects the susceptibility to Doxorubicin]] which affects the cleavage of PARP1 protein]; Acetylcysteine inhibits the reaction [[Verapamil co-treated with gambogic acid] results in increased cleavage of PARP1 protein]; benzyloxycarbonyl-valyl-alanyl-aspartic acid analog inhibits the reaction [Bortezomib promotes the reaction [gambogic acid results in increased cleavage of PARP1 protein]]; benzyloxycarbonyl-valyl-alanyl-aspartic acid analog inhibits the reaction [gambogic acid promotes the reaction [Bortezomib results in increased cleavage of PARP1 protein]]; benzyloxycarbonyl-valyl-alanyl-aspartic acid inhibits the reaction [[Verapamil co-treated with gambogic acid] results in increased cleavage of PARP1 protein]; Bortezomib promotes the reaction [gambogic acid results in increased cleavage of PARP1 protein]; Fluorouracil promotes the reaction [gambogic acid results in decreased expression of PARP1 mRNA]; Fluorouracil promotes the reaction [gambogic acid results in increased cleavage of PARP1 protein]; gambogic acid promotes the reaction [Bortezomib results in increased cleavage of PARP1 protein] 		CTD PMID:19084572 PMID:19464570 PMID:24291039 PMID:24373880 PMID:25824409 NCBI chr13:94,839,484...94,871,295
Ensembl chr13:92,307,586...92,339,404 		JBrowse link
G Rps6kb1 ribosomal protein S6 kinase B1 decreases activity ISO gambogic acid results in decreased activity of RPS6KB1 protein CTD PMID:19433130 NCBI chr10:71,817,794...71,865,211
Ensembl chr10:71,323,777...71,367,908 		JBrowse link
G Tyms thymidylate synthetase decreases expression
multiple interactions 		ISO gambogic acid results in decreased expression of TYMS mRNA
gambogic acid inhibits the reaction [Fluorouracil results in increased expression of TYMS mRNA] 		CTD PMID:19084572 NCBI chr 9:120,760,057...120,776,149
Ensembl chr 9:113,313,452...113,329,536 		JBrowse link
G Umps uridine monophosphate synthetase multiple interactions
increases expression 		ISO Fluorouracil promotes the reaction [gambogic acid results in increased expression of UMPS mRNA] CTD PMID:19084572 NCBI chr11:66,806,107...66,816,520
Ensembl chr11:66,806,045...66,821,903 		JBrowse link
G Wnt5a Wnt family member 5A decreases expression ISO gambogic acid results in decreased expression of WNT5A mRNA; gambogic acid results in decreased expression of WNT5A protein CTD PMID:33533530 NCBI chr16:3,702,300...3,724,860
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 20845
    role 20805
      biological role 20803
        biochemical role 20250
          metabolite 20231
            (-)-gambogic acid 20
Path 2
Term Annotations click to browse term
  CHEBI ontology 20845
    subatomic particle 20843
      composite particle 20843
        hadron 20843
          baryon 20843
            nucleon 20843
              atomic nucleus 20843
                atom 20843
                  main group element atom 20766
                    p-block element atom 20766
                      carbon group element atom 20699
                        carbon atom 20693
                          organic molecular entity 20693
                            heteroorganic entity 20202
                              organochalcogen compound 19890
                                organooxygen compound 19792
                                  carbonyl compound 19423
                                    ketone 17441
                                      cyclic ketone 16029
                                        pyranoxanthones 20
                                          (-)-gambogic acid 20
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