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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:hyperforin
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Accession:CHEBI:5834 term browser browse the term
Definition:A cyclic terpene ketone that is a prenylated carbobicyclic acylphloroglucinol derivative produced by St. John's Wort, Hypericum perforatum.
Synonyms:exact_synonym: (1R,5S,6R,7S)-4-hydroxy-6-methyl-1,3,7-tris(3-methylbut-2-en-1-yl)-6-(4-methylpent-3-en-1-yl)-5-(2-methylpropanoyl)bicyclo[3.3.1]non-3-ene-2,9-dione
 related_synonym: (1R,5S,6R,7S)-4-hydroxy-5-isobutyryl-6-methyl-1,3,7-tris(3-methylbut-2-en-1-yl)-6-(4-methylpent-3-en-1-yl)bicyclo[3.3.1]non-3-ene-2,9-dione;   Formula=C35H52O4;   InChI=1S/C35H52O4/c1-22(2)13-12-19-33(11)27(16-14-23(3)4)21-34(20-18-25(7)8)30(37)28(17-15-24(5)6)31(38)35(33,32(34)39)29(36)26(9)10/h13-15,18,26-27,38H,12,16-17,19-21H2,1-11H3/t27-,33+,34+,35-/m0/s1;   InChIKey=IWBJJCOKGLUQIZ-HQKKAZOISA-N;   SMILES=CC(C)C(=O)[C@@]12C(O)=C(CC=C(C)C)C(=O)[C@@](CC=C(C)C)(C[C@H](CC=C(C)C)[C@@]1(C)CCC=C(C)C)C2=O;   hiperforina;   hyperforine
 xref: Beilstein:6785663;   CAS:11079-53-1;   DrugBank:DB01892;   HMDB:HMDB0030463;   KEGG:C07608;   KNApSAcK:C00034542
 xref_mesh: MESH:C001654
 xref: PDBeChem:HYF;   PMID:12578355;   PMID:16973193;   PMID:21947285;   PMID:22226089;   PMID:22924417;   PMID:23149561;   PMID:23270309;   PMID:23811220;   PMID:24033566;   PMID:24121871;   PMID:24377447;   PMID:24838522;   PMID:24881563;   PMID:25173557;   PMID:25467783;   PMID:25511254;   PMID:25678043;   Reaxys:6785663;   Wikipedia:Hyperforin


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hyperforin 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 increases expression
multiple interactions
ISO hyperforin results in increased expression of ABCB1; hyperforin results in increased expression of ABCB1 mRNA
hyperforin inhibits the reaction [ABCB1 protein results in increased secretion of Ritonavir]
CTD PMID:15266218, PMID:16005588, PMID:24259679 NCBI chr 4:22,339,829...22,517,642
Ensembl chr 4:22,133,521...22,425,515
JBrowse link
G Alas1 5'-aminolevulinate synthase 1 increases expression ISO hyperforin results in increased expression of ALAS1 mRNA CTD PMID:24259679 NCBI chr 8:114,927,704...114,941,038
Ensembl chr 8:114,927,722...114,940,177
JBrowse link
G Bax BCL2 associated X, apoptosis regulator decreases expression
multiple interactions
EXP
ISO
hyperforin results in decreased expression of BAX mRNA
hyperforin inhibits the reaction [aluminum maltolate results in increased expression of BAX mRNA]
CTD PMID:30481499 NCBI chr 1:101,451,801...101,457,207
Ensembl chr 1:101,451,802...101,457,207
JBrowse link
G Bcl2 BCL2, apoptosis regulator multiple interactions
increases expression
ISO
EXP
hyperforin inhibits the reaction [aluminum maltolate results in decreased expression of BCL2 mRNA]
hyperforin results in increased expression of BCL2 mRNA
CTD PMID:30481499 NCBI chr13:26,605,426...26,769,374
Ensembl chr13:26,605,426...26,769,374
JBrowse link
G Casp3 caspase 3 multiple interactions
decreases expression
ISO
EXP
hyperforin inhibits the reaction [aluminum maltolate results in increased activity of CASP3 protein]; hyperforin inhibits the reaction [aluminum maltolate results in increased expression of CASP3 mRNA]
hyperforin results in decreased expression of CASP3 mRNA
CTD PMID:30481499 NCBI chr16:48,845,011...48,863,249
Ensembl chr16:48,845,012...48,863,204
JBrowse link
G Cycs cytochrome c, somatic multiple interactions
decreases expression
EXP
ISO
hyperforin inhibits the reaction [aluminum maltolate results in increased expression of CYCS protein]
hyperforin results in decreased expression of CYCS protein
CTD PMID:30481499 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
decreases activity
ISO hyperforin inhibits the reaction [CYP1A1 protein affects the metabolism of benzo(a)pyrene 7,8-dihydrodiol]
hyperforin results in decreased activity of CYP1A1 protein
CTD PMID:14633740 NCBI chr 8:62,472,087...62,478,122
Ensembl chr 8:62,472,095...62,478,147
JBrowse link
G Cyp24a1 cytochrome P450, family 24, subfamily a, polypeptide 1 increases expression ISO hyperforin results in increased expression of CYP24A1 mRNA CTD PMID:15630458 NCBI chr 3:168,097,484...168,111,920
Ensembl chr 3:168,097,485...168,111,920
JBrowse link
G Cyp2b3 cytochrome P450, family 2, subfamily b, polypeptide 3 increases expression ISO hyperforin results in increased expression of CYP2B6 mRNA CTD PMID:24259679 NCBI chr 1:83,163,103...83,236,615
Ensembl chr 1:83,163,079...83,236,615
JBrowse link
G Cyp3a9 cytochrome P450, family 3, subfamily a, polypeptide 9 increases expression ISO hyperforin results in increased expression of CYP3A5 mRNA CTD PMID:24259679 NCBI chr12:19,074,288...19,114,491
Ensembl chr12:19,074,583...19,114,399
JBrowse link
G Cyp7a1 cytochrome P450 family 7 subfamily A member 1 decreases expression ISO hyperforin results in decreased expression of CYP7A1 mRNA CTD PMID:24259679 NCBI chr 5:19,358,734...19,368,431
Ensembl chr 5:19,358,734...19,368,431
JBrowse link
G Icam1 intercellular adhesion molecule 1 increases expression ISO hyperforin results in increased expression of ICAM1 mRNA CTD PMID:15622447 NCBI chr 8:22,035,287...22,047,049
Ensembl chr 8:22,035,256...22,047,059
JBrowse link
G Jun Jun proto-oncogene, AP-1 transcription factor subunit multiple interactions ISO hyperforin promotes the reaction [JUN protein binds to CXCL8 promoter] CTD PMID:15622447 NCBI chr 5:114,011,184...114,014,277
Ensembl chr 5:114,011,189...114,014,277
JBrowse link
G Mapk1 mitogen activated protein kinase 1 increases phosphorylation ISO hyperforin results in increased phosphorylation of MAPK1 protein CTD PMID:15622447 NCBI chr11:88,203,863...88,273,301
Ensembl chr11:88,211,599...88,273,254
JBrowse link
G Mapk3 mitogen activated protein kinase 3 increases phosphorylation ISO hyperforin results in increased phosphorylation of MAPK3 protein CTD PMID:15622447 NCBI chr 1:198,192,773...198,198,975
Ensembl chr 1:198,192,773...198,198,975
JBrowse link
G Nr1i2 nuclear receptor subfamily 1, group I, member 2 multiple interactions
increases response to substance
affects binding
increases activity
ISO [NR1I2 protein co-treated with hyperforin] results in decreased expression of SLC22A1 mRNA; [NR1I2 protein results in increased susceptibility to hyperforin] which results in decreased expression of SLC22A1 mRNA; hyperforin binds to and results in increased activity of NR1I2 protein; hyperforin promotes the reaction [NR1I2 protein results in decreased expression of SLC22A1 mRNA]; NR1I2 protein affects the reaction [hyperforin results in increased expression of CYP2C9 mRNA]; NR1I2 protein promotes the reaction [hyperforin results in increased abundance of Lipids]
hyperforin binds to NR1I2 protein
hyperforin results in increased activity of NR1I2 protein
CTD PMID:14600250, PMID:15630458, PMID:15856409, PMID:20079722, PMID:26187274, PMID:26920453, PMID:27071811 NCBI chr11:65,022,100...65,058,546
Ensembl chr11:65,022,100...65,058,545
JBrowse link
G Por cytochrome p450 oxidoreductase increases expression ISO hyperforin results in increased expression of POR mRNA CTD PMID:24259679 NCBI chr12:23,998,411...24,017,063
Ensembl chr12:23,998,411...24,046,814
JBrowse link
G Slc22a1 solute carrier family 22 member 1 decreases expression
multiple interactions
ISO hyperforin results in decreased expression of SLC22A1 protein
[NR1I2 protein co-treated with hyperforin] results in decreased expression of SLC22A1 mRNA; [NR1I2 protein results in increased susceptibility to hyperforin] which results in decreased expression of SLC22A1 mRNA; hyperforin promotes the reaction [NR1I2 protein results in decreased expression of SLC22A1 mRNA]
CTD PMID:26920453 NCBI chr 1:48,273,639...48,300,645
Ensembl chr 1:48,273,611...48,300,655
JBrowse link
G Ugt1a1 UDP glucuronosyltransferase family 1 member A1 increases expression ISO hyperforin results in increased expression of UGT1A1 mRNA CTD PMID:24259679 NCBI chr 9:95,295,701...95,302,822
Ensembl chr 9:95,161,157...95,302,822
JBrowse link

Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19787
    role 19734
      application 19393
        anti-inflammatory agent 14950
          hyperforin 19
Path 2
Term Annotations click to browse term
  CHEBI ontology 19787
    subatomic particle 19784
      composite particle 19784
        hadron 19784
          baryon 19784
            nucleon 19784
              atomic nucleus 19784
                atom 19784
                  main group element atom 19672
                    p-block element atom 19672
                      carbon group element atom 19574
                        carbon atom 19563
                          organic molecular entity 19563
                            organic group 18495
                              organic divalent group 18488
                                organodiyl group 18488
                                  carbonyl group 18391
                                    carbonyl compound 18391
                                      ketone 16144
                                        cyclic ketone 13813
                                          alicyclic ketone 1047
                                            cyclic terpene ketone 128
                                              hyperforin 19
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RGD is funded by grant HL64541 from the National Heart, Lung, and Blood Institute on behalf of the NIH.