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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:kahweol
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Accession:CHEBI:138308 term browser browse the term
Definition:A diterpenoid with formula C20H26O3, isolated from the beans of Coffea arabica. It exhibits antioxidant, anti-inflammatory, anti-angiogenesis and anti-proliferative properties.
Synonyms:exact_synonym: (1S,4S,12S,13R,16R,17R)-17-(hydroxymethyl)-12-methyl-8-oxapentacyclo[14.2.1.0(1,13).0(4,12).0(5,9)]nonadeca-5(9),6,10-trien-17-ol;   (3bS,5aS,7R,8R,10aR,10bS)-7-(hydroxymethyl)-10b-methyl-3b,4,5,6,7,8,9,10,10a,10b-decahydro-5a,8-methanocyclohepta[5,6]naphtho[2,1-b]furan-7-ol
 related_synonym: CCRIS-1521;   Formula=C20H26O3;   InChI=1S/C20H26O3/c1-18-7-5-16-14(6-9-23-16)15(18)4-8-19-10-13(2-3-17(18)19)20(22,11-19)12-21/h5-7,9,13,15,17,21-22H,2-4,8,10-12H2,1H3/t13-,15-,17+,18-,19+,20+/m1/s1;   InChIKey=JEKMKNDURXDJAD-HWUKTEKMSA-N;   SMILES=[C@]123[C@]([H])([C@@]4(C)[C@@](C5=C(C=C4)OC=C5)(CC1)[H])CC[C@H](C2)[C@@](C3)(O)CO
 xref: CAS:6894-43-5;   FooDB:FDB014295;   HMDB:HMDB0035602
 xref_mesh: MESH:C053401
 xref: MetaCyc:CPD-16468;   PMID:17590492;   PMID:21858104;   PMID:24209317;   PMID:27424123;   PMID:27748804;   PMID:27871156;   PMID:30205135;   PMID:3612687;   Wikipedia:Kahweol


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kahweol term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Akr7a3 aldo-keto reductase family 7 member A3 multiple interactions EXP [cafestol co-treated with kahweol] inhibits the reaction [ochratoxin A results in decreased expression of AKR7A3 protein] CTD PMID:17110534 NCBI chr 5:157,801,120...157,813,756
Ensembl chr 5:157,801,163...157,813,756
JBrowse link
G Akt1 AKT serine/threonine kinase 1 multiple interactions
decreases phosphorylation
ISO 2-(4-morpholinyl)-8-phenyl-4H-1-benzopyran-4-one promotes the reaction [kahweol results in decreased phosphorylation of AKT1 protein]; kahweol promotes the reaction [2-(4-morpholinyl)-8-phenyl-4H-1-benzopyran-4-one results in decreased phosphorylation of AKT1 protein] CTD PMID:30205135 NCBI chr 6:137,218,398...137,239,970
Ensembl chr 6:137,218,376...137,236,258
JBrowse link
G Bax BCL2 associated X, apoptosis regulator multiple interactions ISO kahweol inhibits the reaction [Hydrogen Peroxide results in increased expression of BAX protein] CTD PMID:31306736 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 ISO kahweol inhibits the reaction [Hydrogen Peroxide results in decreased expression of BCL2 protein] CTD PMID:31306736 NCBI chr13:26,605,426...26,769,374
Ensembl chr13:26,605,426...26,769,374
JBrowse link
G Casp3 caspase 3 multiple interactions ISO ERBB2 protein affects the reaction [kahweol results in increased activity of and results in increased cleavage of CASP3 protein]; kahweol inhibits the reaction [Hydrogen Peroxide results in increased activity of CASP3 protein]; kahweol results in increased activity of and results in increased cleavage of CASP3 protein CTD PMID:30205135 PMID:31306736 NCBI chr16:48,845,011...48,863,249
Ensembl chr16:48,845,012...48,863,204
JBrowse link
G Casp9 caspase 9 multiple interactions ISO kahweol inhibits the reaction [Hydrogen Peroxide results in increased activity of CASP9 protein] CTD PMID:31306736 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
multiple interactions
ISO kahweol results in decreased expression of CCND1 protein
2-(2-amino-3-methoxyphenyl)-4H-1-benzopyran-4-one inhibits the reaction [kahweol results in decreased expression of CCND1 protein]; 2-(2-amino-3-methoxyphenyl)-4H-1-benzopyran-4-one inhibits the reaction [kahweol results in increased phosphorylation of CCND1 protein]; benzyloxycarbonylleucyl-leucyl-leucine aldehyde inhibits the reaction [kahweol results in decreased expression of CCND1 protein]; kahweol results in increased phosphorylation of and results in increased degradation of CCND1 protein; leptomycin B inhibits the reaction [kahweol results in increased degradation of CCND1 protein]; Lithium Chloride inhibits the reaction [kahweol results in decreased expression of CCND1 protein]; Lithium Chloride inhibits the reaction [kahweol results in increased phosphorylation of CCND1 protein]; pyrazolanthrone inhibits the reaction [kahweol results in decreased expression of CCND1 protein]; pyrazolanthrone inhibits the reaction [kahweol results in increased phosphorylation of CCND1 protein]
CTD PMID:27424123 PMID:30205135 NCBI chr 1:218,090,750...218,100,447
Ensembl chr 1:218,090,750...218,100,325
JBrowse link
G Cyp2c11 cytochrome P450, subfamily 2, polypeptide 11 multiple interactions EXP [cafestol co-treated with kahweol] results in decreased expression of CYP2C11; [cafestol co-treated with kahweol] results in decreased expression of CYP2C11 protein CTD PMID:9744531 PMID:11346484 NCBI chr 1:257,676,172...258,004,428
Ensembl chr 1:257,970,345...258,004,434
JBrowse link
G Cyp2e1 cytochrome P450, family 2, subfamily e, polypeptide 1 decreases activity ISO kahweol results in decreased activity of CYP2E1 protein CTD PMID:17590492 NCBI chr 1:213,511,892...213,522,195
Ensembl chr 1:213,511,874...213,535,542
JBrowse link
G Cyp3a2 cytochrome P450, family 3, subfamily a, polypeptide 2 multiple interactions EXP [cafestol co-treated with kahweol] results in decreased expression of CYP3A2; [cafestol co-treated with kahweol] results in decreased expression of CYP3A2 protein CTD PMID:9744531 PMID:11346484 NCBI chr12:11,641,500...11,677,818
Ensembl chr12:11,655,402...11,733,136
JBrowse link
G Erbb2 erb-b2 receptor tyrosine kinase 2 decreases expression
multiple interactions
ISO kahweol results in decreased expression of ERBB2 mRNA; kahweol results in decreased expression of ERBB2 protein
2-(4-morpholinyl)-8-phenyl-4H-1-benzopyran-4-one promotes the reaction [kahweol results in decreased expression of ERBB2 mRNA]; ERBB2 protein affects the reaction [kahweol results in increased activity of and results in increased cleavage of CASP3 protein]; kahweol promotes the reaction [2-(4-morpholinyl)-8-phenyl-4H-1-benzopyran-4-one results in decreased expression of ERBB2 mRNA]
CTD PMID:30205135 NCBI chr10:86,367,596...86,391,728
Ensembl chr10:86,367,596...86,391,728
JBrowse link
G Etv4 ETS variant transcription factor 4 increases expression ISO kahweol results in increased expression of ETV4 mRNA; kahweol results in increased expression of ETV4 protein CTD PMID:30205135 NCBI chr10:89,685,058...89,700,300
Ensembl chr10:89,685,058...89,700,283
JBrowse link
G Fasn fatty acid synthase decreases expression
multiple interactions
ISO kahweol results in decreased expression of FASN mRNA; kahweol results in decreased expression of FASN protein
2-(4-morpholinyl)-8-phenyl-4H-1-benzopyran-4-one promotes the reaction [kahweol results in decreased expression of FASN mRNA]; 2-(4-morpholinyl)-8-phenyl-4H-1-benzopyran-4-one promotes the reaction [kahweol results in decreased expression of FASN protein]; kahweol promotes the reaction [2-(4-morpholinyl)-8-phenyl-4H-1-benzopyran-4-one results in decreased expression of FASN mRNA]; kahweol promotes the reaction [2-(4-morpholinyl)-8-phenyl-4H-1-benzopyran-4-one results in decreased expression of FASN protein]
CTD PMID:30205135 NCBI chr10:109,987,735...110,005,901
Ensembl chr10:109,987,735...110,005,901
JBrowse link
G Gclc glutamate-cysteine ligase, catalytic subunit multiple interactions EXP [cafestol co-treated with kahweol] inhibits the reaction [ochratoxin A results in decreased expression of GCLC protein] CTD PMID:17110534 NCBI chr 8:85,059,051...85,097,471
Ensembl chr 8:85,059,051...85,097,468
JBrowse link
G Gsk3b glycogen synthase kinase 3 beta increases phosphorylation
decreases phosphorylation
ISO kahweol results in increased phosphorylation of GSK3B protein
kahweol results in decreased phosphorylation of GSK3B protein
CTD PMID:27424123 PMID:30205135 NCBI chr11:65,060,884...65,208,842
Ensembl chr11:65,066,235...65,209,268
JBrowse link
G Gsta5 glutathione S-transferase alpha 5 multiple interactions EXP [cafestol co-treated with kahweol] inhibits the reaction [ochratoxin A results in decreased expression of GSTA5 protein]; [cafestol co-treated with kahweol] results in increased expression of GSTA5; [cafestol co-treated with kahweol] results in increased expression of GSTA5 protein CTD PMID:9744531 PMID:11346484 PMID:17110534 NCBI chr 8:85,553,659...85,564,914
Ensembl chr 8:85,553,734...85,565,179
JBrowse link
G Gstm1 glutathione S-transferase mu 1 multiple interactions ISO [cafestol co-treated with kahweol] results in increased expression of GSTM1 protein CTD PMID:11346484 NCBI chr 2:210,803,869...210,809,461
Ensembl chr 2:210,803,869...210,809,306
JBrowse link
G Gstp1 glutathione S-transferase pi 1 multiple interactions EXP [cafestol co-treated with kahweol] inhibits the reaction [ochratoxin A results in decreased expression of GSTP1 protein] CTD PMID:17110534 NCBI chr 1:219,291,679...219,294,147
Ensembl chr 1:219,291,679...219,294,147
JBrowse link
G Hmox1 heme oxygenase 1 multiple interactions ISO 2-(4-morpholinyl)-8-phenyl-4H-1-benzopyran-4-one inhibits the reaction [kahweol results in increased expression of and results in increased activity of HMOX1 protein]; kahweol results in increased expression of and results in increased activity of HMOX1 protein; NFE2L2 protein affects the reaction [kahweol results in increased expression of HMOX1 protein]; SB 203580 inhibits the reaction [kahweol results in increased expression of and results in increased activity of HMOX1 protein] CTD PMID:31306736 NCBI chr19:14,508,634...14,515,455
Ensembl chr19:14,508,616...14,515,456
JBrowse link
G Il1b interleukin 1 beta multiple interactions ISO kahweol inhibits the reaction [Hydrogen Peroxide results in increased expression of IL1B protein] CTD PMID:31306736 NCBI chr 3:121,876,256...121,882,637
Ensembl chr 3:121,876,263...121,882,726
JBrowse link
G Mapk1 mitogen activated protein kinase 1 increases phosphorylation ISO kahweol results in increased phosphorylation of MAPK1 protein CTD PMID:27424123 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 kahweol results in increased phosphorylation of MAPK3 protein CTD PMID:27424123 NCBI chr 1:198,192,773...198,198,975
Ensembl chr 1:198,192,773...198,198,975
JBrowse link
G Mtor mechanistic target of rapamycin kinase decreases phosphorylation ISO kahweol results in decreased phosphorylation of MTOR protein CTD PMID:30205135 NCBI chr 5:165,263,813...165,373,967
Ensembl chr 5:165,263,800...165,373,967
JBrowse link
G Nfe2l2 nuclear factor, erythroid 2-like 2 multiple interactions EXP
ISO
[cafestol co-treated with kahweol] inhibits the reaction [ochratoxin A results in decreased activity of NFE2L2 protein]
NFE2L2 protein affects the reaction [kahweol results in increased expression of HMOX1 protein]
NFE2L2 protein affects the reaction [[cafestol co-treated with kahweol] results in decreased susceptibility to Acrolein]; NFE2L2 protein promotes the reaction [[cafestol co-treated with kahweol] results in increased expression of NQO1 mRNA]
CTD PMID:17110534 PMID:18028974 PMID:31306736 NCBI chr 3:62,497,568...62,525,146
Ensembl chr 3:62,497,571...62,524,996
JBrowse link
G Nqo1 NAD(P)H quinone dehydrogenase 1 multiple interactions EXP
ISO
[cafestol co-treated with kahweol] inhibits the reaction [ochratoxin A results in decreased expression of NQO1 protein]
[cafestol co-treated with kahweol] results in increased expression of NQO1 mRNA; [cafestol co-treated with kahweol] results in increased expression of NQO1 protein; NFE2L2 protein promotes the reaction [[cafestol co-treated with kahweol] results in increased expression of NQO1 mRNA]
CTD PMID:17110534 PMID:18028974 NCBI chr19:38,422,210...38,437,103
Ensembl chr19:38,422,164...38,437,180
JBrowse link
G Ogdh oxoglutarate dehydrogenase multiple interactions ISO kahweol inhibits the reaction [Hydrogen Peroxide results in decreased activity of OGDH protein] CTD PMID:31306736 NCBI chr14:86,414,924...86,481,903
Ensembl chr14:86,414,949...86,613,327
JBrowse link
G Parp1 poly (ADP-ribose) polymerase 1 increases cleavage
multiple interactions
ISO kahweol results in increased cleavage of PARP1 protein
kahweol inhibits the reaction [Hydrogen Peroxide results in increased cleavage of PARP1 protein]
CTD PMID:30205135 PMID:31306736 NCBI chr13:98,857,255...98,889,444
Ensembl chr13:98,857,177...98,889,716
JBrowse link
G Srebf1 sterol regulatory element binding transcription factor 1 multiple interactions
decreases expression
ISO 2-(4-morpholinyl)-8-phenyl-4H-1-benzopyran-4-one promotes the reaction [kahweol results in decreased expression of SREBF1 protein]; kahweol promotes the reaction [2-(4-morpholinyl)-8-phenyl-4H-1-benzopyran-4-one results in decreased expression of SREBF1 protein]
kahweol results in decreased expression of SREBF1 mRNA; kahweol results in decreased expression of SREBF1 protein
CTD PMID:30205135 NCBI chr10:46,570,996...46,593,021
Ensembl chr10:46,570,996...46,593,009
JBrowse link
G Sult1a1 sulfotransferase family 1A member 1 multiple interactions ISO [cafestol co-treated with kahweol] results in decreased activity of SULT1A1 protein CTD PMID:15680679 NCBI chr 1:198,100,586...198,104,106
Ensembl chr 1:198,100,586...198,104,109
JBrowse link
G Tfap2a transcription factor AP-2 alpha decreases expression ISO kahweol results in decreased expression of TFAP2A mRNA; kahweol results in decreased expression of TFAP2A protein CTD PMID:30205135 NCBI chr17:24,653,342...24,670,457
Ensembl chr17:24,654,902...24,670,457
JBrowse link
G Tnf tumor necrosis factor multiple interactions ISO kahweol inhibits the reaction [Hydrogen Peroxide results in increased expression of TNF protein] CTD PMID:31306736 NCBI chr20:5,189,382...5,192,000
Ensembl chr20:5,189,390...5,192,000
Ensembl chr20:5,189,390...5,192,000
JBrowse link

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  CHEBI ontology 19770
    role 19720
      chemical role 19260
        antioxidant 14254
          kahweol 31
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  CHEBI ontology 19770
    subatomic particle 19768
      composite particle 19768
        hadron 19768
          baryon 19768
            nucleon 19768
              atomic nucleus 19768
                atom 19768
                  main group element atom 19662
                    main group molecular entity 19662
                      s-block molecular entity 19429
                        hydrogen molecular entity 19423
                          hydrides 18758
                            organic hydride 18356
                              organic fundamental parent 18356
                                hydrocarbon 18075
                                  terpene 12594
                                    diterpene 11395
                                      diterpenoid 11395
                                        kahweol 31
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