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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 5:151,590,968...151,601,394
Ensembl chr 5:151,584,479...151,601,394
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 6:131,713,716...131,735,319
Ensembl chr 6:131,713,720...131,733,921
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 1:95,940,001...95,945,407
Ensembl chr 1:95,938,808...95,945,368
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 chr13:22,689,783...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 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 chr16:45,662,910...45,681,171
Ensembl chr16:45,662,910...45,684,648
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 5:154,108,872...154,126,628
Ensembl chr 5:154,109,046...154,126,626
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 1:200,089,002...200,098,524
Ensembl chr 1:200,089,002...200,098,602
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 1:236,762,719...236,799,069
Ensembl chr 1:236,762,842...236,799,066
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 1:195,840,330...195,850,728
Ensembl chr 1:195,840,058...195,864,023
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 chr12:9,207,978...9,230,064
Ensembl chr12:9,015,383...9,285,008
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 chr10:83,411,197...83,435,078
Ensembl chr10:83,411,313...83,435,078
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 chr10:86,706,749...86,721,974
Ensembl chr10:86,706,749...86,721,974
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 chr10:106,072,093...106,090,259
Ensembl chr10:106,072,091...106,090,261
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 8:78,629,899...78,668,547
Ensembl chr 8:78,630,127...78,668,544
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 chr11:62,498,997...62,648,665
Ensembl chr11:62,504,316...62,648,646
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 8:79,105,561...79,117,472
Ensembl chr 8:79,105,661...79,117,472
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 2:195,649,845...195,655,402
Ensembl chr 2:195,649,845...195,655,411
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 1:201,337,762...201,340,230
Ensembl chr 1:201,321,672...201,340,226
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 chr19:13,466,287...13,474,082
Ensembl chr19:13,467,244...13,474,079
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 3:116,577,005...116,583,386
Ensembl chr 3:116,577,010...116,583,415
JBrowse link
G Mapk1 mitogen activated protein kinase 1 increases phosphorylation ISO kahweol results in increased phosphorylation of MAPK1 protein CTD PMID:27424123 NCBI chr11:83,957,813...84,023,629
Ensembl chr11:83,957,813...84,023,616
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 1:181,366,646...181,372,863
Ensembl chr 1:181,366,637...181,372,863
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 5:158,884,856...158,994,311
Ensembl chr 5:158,884,804...158,994,311
JBrowse link
G Nfe2l2 NFE2 like bZIP transcription factor 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 [[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]
NFE2L2 protein affects the reaction [kahweol results in increased expression of HMOX1 protein]
CTD PMID:17110534 PMID:18028974 PMID:31306736 NCBI chr 3:60,594,239...60,621,712
Ensembl chr 3:60,594,242...60,621,737
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 chr19:35,295,633...35,310,528
Ensembl chr19:35,295,573...35,310,557
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 chr14:81,150,021...81,217,479
Ensembl chr14:81,150,091...81,217,479
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 chr13:92,307,593...92,339,406
Ensembl chr13:92,307,586...92,339,404
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 chr10:45,007,637...45,029,650
Ensembl chr10:45,007,637...45,029,650
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 1:181,272,022...181,276,750
Ensembl chr 1:181,272,023...181,275,562
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 chr17:24,028,716...24,047,507
Ensembl chr17:24,024,432...24,047,507
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 chr20:3,622,011...3,624,629
Ensembl chr20:3,622,011...3,624,629
JBrowse link

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  CHEBI ontology 19918
    role 19894
      chemical role 19512
        antioxidant 16062
          kahweol 31
Path 2
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  CHEBI ontology 19918
    subatomic particle 19916
      composite particle 19916
        hadron 19916
          baryon 19916
            nucleon 19916
              atomic nucleus 19916
                atom 19916
                  main group element atom 19866
                    main group molecular entity 19866
                      s-block molecular entity 19698
                        hydrogen molecular entity 19684
                          hydrides 19159
                            organic hydride 18714
                              organic fundamental parent 18714
                                hydrocarbon 18440
                                  terpene 13849
                                    diterpene 12815
                                      diterpenoid 12815
                                        kahweol 31
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