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: phloroglucinol
Accession: CHEBI:16204
browse the term
Definition: A benzenetriol with hydroxy groups at position 1, 3 and 5.
Synonyms: related_synonym: 1,3,5-Benzenetriol; 1,3,5-trihydroxybenzene; Formula=C6H6O3; InChI=1S/C6H6O3/c7-4-1-5(8)3-6(9)2-4/h1-3,7-9H; InChIKey=QCDYQQDYXPDABM-UHFFFAOYSA-N; SMILES=Oc1cc(O)cc(O)c1; benzene-1,3,5-triol; s-Trihydroxybenzene
alt_id: CHEBI:11159; CHEBI:14788; CHEBI:22710; CHEBI:8114
xref: CAS:108-73-6; Drug_Central:2153; HMDB:HMDB0013675; KEGG:C02183; KEGG:D00152; KNApSAcK:C00002665
xref_mesh: MESH:D010696
xref: MetaCyc:CPD-16; PMID:25456733; PMID:25640118; Reaxys:1341907; UM-BBD_compID:c0026; Wikipedia:Phloroglucinol
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Akt1
AKT serine/threonine kinase 1
decreases phosphorylation
ISO
Phloroglucinol analog results in decreased phosphorylation of AKT1 protein
CTD
PMID:23178381
NCBI chr 6:137,218,398...137,239,970
Ensembl chr 6:137,218,376...137,236,258
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Bax
BCL2 associated X, apoptosis regulator
increases expression
ISO
Phloroglucinol metabolite results in increased expression of BAX protein
CTD
PMID:22796323
NCBI chr 1:101,451,801...101,457,207
Ensembl chr 1:101,451,802...101,457,207
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Bcl2
BCL2, apoptosis regulator
decreases expression
ISO
Phloroglucinol metabolite results in decreased expression of BCL2 protein
CTD
PMID:22796323
NCBI chr13:26,605,426...26,769,374
Ensembl chr13:26,605,426...26,769,374
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Casp3
caspase 3
increases cleavage
ISO
Phloroglucinol analog results in increased cleavage of CASP3 protein; Phloroglucinol metabolite results in increased cleavage of CASP3 protein
CTD
PMID:22796323 PMID:23178381
NCBI chr16:48,845,011...48,863,249
Ensembl chr16:48,845,012...48,863,204
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Casp9
caspase 9
increases cleavage
ISO
Phloroglucinol metabolite results in increased cleavage of CASP9 protein
CTD
PMID:22796323
NCBI chr 5:160,356,211...160,373,774
Ensembl chr 5:160,355,833...160,373,778
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Ccn2
cellular communication network factor 2
multiple interactions
ISO
Phloroglucinol analog inhibits the reaction [TGFB1 protein results in increased expression of CCN2 protein]
CTD
PMID:26054450
NCBI chr 1:21,851,657...21,854,773
Ensembl chr 1:21,851,660...21,854,773
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Gclc
glutamate-cysteine ligase, catalytic subunit
increases expression
ISO
Phloroglucinol results in increased expression of GCLC protein
CTD
PMID:20188716
NCBI chr 8:85,059,051...85,097,471
Ensembl chr 8:85,059,051...85,097,468
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Gdf15
growth differentiation factor 15
increases expression
ISO
Phloroglucinol analog results in increased expression of GDF15 protein
CTD
PMID:23178381
NCBI chr16:20,555,395...20,557,978
Ensembl chr16:20,555,395...20,557,978
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Gsk3b
glycogen synthase kinase 3 beta
decreases phosphorylation
ISO
Phloroglucinol analog results in decreased phosphorylation of GSK3B protein
CTD
PMID:23178381
NCBI chr11:65,060,884...65,208,842
Ensembl chr11:65,066,235...65,209,268
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Parp1
poly (ADP-ribose) polymerase 1
increases cleavage
ISO
Phloroglucinol analog results in increased cleavage of PARP1 protein; Phloroglucinol metabolite results in increased cleavage of PARP1 protein
CTD
PMID:22796323 PMID:23178381
NCBI chr13:98,857,255...98,889,444
Ensembl chr13:98,857,177...98,889,716
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Smad2
SMAD family member 2
multiple interactions
ISO
Phloroglucinol analog inhibits the reaction [TGFB1 protein results in increased phosphorylation of SMAD2 protein]
CTD
PMID:26054450
NCBI chr18:72,550,107...72,612,078
Ensembl chr18:72,550,219...72,612,078
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Smad3
SMAD family member 3
multiple interactions
ISO
Phloroglucinol analog inhibits the reaction [TGFB1 protein results in increased phosphorylation of SMAD3 protein]
CTD
PMID:26054450
NCBI chr 8:68,569,530...68,678,349
Ensembl chr 8:68,569,530...68,678,349
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Tgfb1
transforming growth factor, beta 1
multiple interactions
ISO
Phloroglucinol analog inhibits the reaction [TGFB1 protein results in increased expression of CCN2 protein]; Phloroglucinol analog inhibits the reaction [TGFB1 protein results in increased phosphorylation of SMAD2 protein]; Phloroglucinol analog inhibits the reaction [TGFB1 protein results in increased phosphorylation of SMAD3 protein]
CTD
PMID:26054450
NCBI chr 1:82,480,875...82,497,196
Ensembl chr 1:82,480,195...82,497,199
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Bax
BCL2 associated X, apoptosis regulator
increases expression
ISO
aspidin BB results in increased expression of BAX protein
CTD
PMID:23628508
NCBI chr 1:101,451,801...101,457,207
Ensembl chr 1:101,451,802...101,457,207
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Bcl2
BCL2, apoptosis regulator
decreases expression
ISO
aspidin BB results in decreased expression of BCL2 protein
CTD
PMID:23628508
NCBI chr13:26,605,426...26,769,374
Ensembl chr13:26,605,426...26,769,374
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Casp3
caspase 3
increases activity increases expression
ISO
aspidin BB results in increased activity of CASP3 protein aspidin BB results in increased expression of CASP3 protein modified form
CTD
PMID:23628508
NCBI chr16:48,845,011...48,863,249
Ensembl chr16:48,845,012...48,863,204
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Ccna2
cyclin A2
increases expression
ISO
aspidin BB results in increased expression of CCNA2 protein
CTD
PMID:23628508
NCBI chr 2:123,274,727...123,282,266
Ensembl chr 2:123,275,881...123,282,214
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Ccne1
cyclin E1
increases expression
ISO
aspidin BB results in increased expression of CCNE1 protein
CTD
PMID:23628508
NCBI chr 1:94,485,830...94,495,112
Ensembl chr 1:94,485,832...94,494,980
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Cdk2
cyclin dependent kinase 2
increases expression
ISO
aspidin BB results in increased expression of CDK2 protein
CTD
PMID:23628508
NCBI chr 7:3,124,953...3,132,533
Ensembl chr 7:3,124,954...3,132,457
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Cycs
cytochrome c, somatic
affects localization
ISO
aspidin BB affects the localization of CYCS protein
CTD
PMID:23628508
NCBI chr 4:80,331,226...80,333,326
Ensembl chr 4:80,331,227...80,333,326
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E2f1
E2F transcription factor 1
increases expression
ISO
aspidin BB results in increased expression of E2F1 protein
CTD
PMID:23628508
NCBI chr 3:150,062,895...150,073,721
Ensembl chr 3:150,047,826...150,073,721
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Parp1
poly (ADP-ribose) polymerase 1
increases expression
ISO
aspidin BB results in increased expression of PARP1 protein modified form
CTD
PMID:23628508
NCBI chr13:98,857,255...98,889,444
Ensembl chr13:98,857,177...98,889,716
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Rb1
RB transcriptional corepressor 1
increases expression
ISO
aspidin BB results in increased expression of RB1 protein
CTD
PMID:23628508
NCBI chr15:55,081,582...55,209,060
Ensembl chr15:55,083,140...55,209,342
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Akt1
AKT serine/threonine kinase 1
multiple interactions
ISO
dieckol results in decreased expression of and results in decreased phosphorylation of AKT1 protein
CTD
PMID:31291034
NCBI chr 6:137,218,398...137,239,970
Ensembl chr 6:137,218,376...137,236,258
G
Casp3
caspase 3
increases activity
ISO
dieckol results in increased activity of CASP3 protein
CTD
PMID:31291034
NCBI chr16:48,845,011...48,863,249
Ensembl chr16:48,845,012...48,863,204
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Casp8
caspase 8
increases activity
ISO
dieckol results in increased activity of CASP8 protein
CTD
PMID:31291034
NCBI chr 9:65,614,142...65,662,624
Ensembl chr 9:65,614,142...65,662,106
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Casp9
caspase 9
increases activity
ISO
dieckol results in increased activity of CASP9 protein
CTD
PMID:31291034
NCBI chr 5:160,356,211...160,373,774
Ensembl chr 5:160,355,833...160,373,778
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Cdh1
cadherin 1
increases expression
ISO
dieckol results in increased expression of CDH1 protein
CTD
PMID:31291034
NCBI chr19:38,768,467...38,838,395
Ensembl chr19:38,768,467...38,838,395
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Cdh2
cadherin 2
decreases expression
ISO
dieckol results in decreased expression of CDH2 protein
CTD
PMID:31291034
NCBI chr18:8,146,971...8,366,037
Ensembl chr18:8,146,971...8,360,684
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Mmp1
matrix metallopeptidase 1
decreases expression
ISO
dieckol results in decreased expression of MMP1 mRNA; dieckol results in decreased expression of MMP1 protein
CTD
PMID:19330880
NCBI chr 8:5,703,206...5,723,593
Ensembl chr 8:5,703,206...5,723,591
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Mmp13
matrix metallopeptidase 13
decreases expression
ISO
dieckol results in decreased expression of MMP13 mRNA; dieckol results in decreased expression of MMP13 protein
CTD
PMID:19330880
NCBI chr 8:5,522,739...5,533,018
Ensembl chr 8:5,522,739...5,533,018
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Mmp3
matrix metallopeptidase 3
decreases expression
ISO
dieckol results in decreased expression of MMP3 mRNA; dieckol results in decreased expression of MMP3 protein
CTD
PMID:19330880
NCBI chr 8:5,676,608...5,698,579
Ensembl chr 8:5,676,665...5,698,579
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Mmp9
matrix metallopeptidase 9
decreases expression
ISO
dieckol results in decreased expression of MMP9 protein
CTD
PMID:31291034
NCBI chr 3:161,413,410...161,421,473
Ensembl chr 3:161,413,298...161,421,520
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Mtor
mechanistic target of rapamycin kinase
decreases phosphorylation
ISO
dieckol results in decreased phosphorylation of MTOR protein
CTD
PMID:31291034
NCBI chr 5:165,263,813...165,373,967
Ensembl chr 5:165,263,800...165,373,967
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Nos2
nitric oxide synthase 2
decreases expression
ISO
dieckol results in decreased expression of NOS2 mRNA; dieckol results in decreased expression of NOS2 protein
CTD
PMID:19330880
NCBI chr10:66,188,290...66,221,621
Ensembl chr10:66,189,786...66,313,190
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Plau
plasminogen activator, urokinase
decreases expression
ISO
dieckol results in decreased expression of PLAU protein
CTD
PMID:31291034
NCBI chr15:3,644,296...3,650,765
Ensembl chr15:3,644,769...3,650,819
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Ptgs2
prostaglandin-endoperoxide synthase 2
decreases expression
ISO
dieckol results in decreased expression of PTGS2 mRNA; dieckol results in decreased expression of PTGS2 protein
CTD
PMID:19330880
NCBI chr13:67,351,230...67,356,920
Ensembl chr13:67,351,087...67,359,335
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Rps6kb1
ribosomal protein S6 kinase B1
decreases expression
ISO
dieckol results in decreased expression of RPS6KB1 protein
CTD
PMID:31291034
NCBI chr10:73,824,200...73,865,503
Ensembl chr10:73,824,202...73,865,364
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Twist1
twist family bHLH transcription factor 1
decreases expression
ISO
dieckol results in decreased expression of TWIST1 protein
CTD
PMID:31291034
NCBI chr 6:53,401,241...53,403,235
Ensembl chr 6:53,401,109...53,403,214
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Vim
vimentin
decreases expression
ISO
dieckol results in decreased expression of VIM protein
CTD
PMID:31291034
NCBI chr17:80,882,715...80,891,200
Ensembl chr17:80,882,666...80,891,212
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Akt1
AKT serine/threonine kinase 1
multiple interactions
ISO
eckol results in decreased phosphorylation of and results in decreased activity of AKT1 protein
CTD
PMID:21514314
NCBI chr 6:137,218,398...137,239,970
Ensembl chr 6:137,218,376...137,236,258
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Casp8
caspase 8
multiple interactions
ISO
[eckol co-treated with temozolomide] results in increased cleavage of CASP8 protein
CTD
PMID:21514314
NCBI chr 9:65,614,142...65,662,624
Ensembl chr 9:65,614,142...65,662,106
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Ctnnb1
catenin beta 1
decreases expression
ISO
eckol results in decreased expression of CTNNB1 protein
CTD
PMID:21514314
NCBI chr 8:129,601,511...129,628,378
Ensembl chr 8:129,617,812...129,627,372
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Cybb
cytochrome b-245 beta chain
decreases expression
ISO
eckol results in decreased expression of CYBB protein
CTD
PMID:21514314
NCBI chr X:14,578,330...14,610,049
Ensembl chr X:14,578,264...14,612,547
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Foxo3
forkhead box O3
increases phosphorylation multiple interactions
ISO
eckol results in increased phosphorylation of FOXO3 protein FOXO3 mutant form inhibits the reaction [eckol results in increased expression of SOD2 protein]
CTD
PMID:24700636
NCBI chr20:46,428,078...46,519,156
Ensembl chr20:46,428,124...46,519,144
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Mapk1
mitogen activated protein kinase 1
multiple interactions
ISO
eckol results in decreased phosphorylation of and results in decreased activity of MAPK1 protein
CTD
PMID:21514314
NCBI chr11:88,203,863...88,273,301
Ensembl chr11:88,211,599...88,273,254
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Mapk3
mitogen activated protein kinase 3
multiple interactions
ISO
eckol results in decreased phosphorylation of and results in decreased activity of MAPK3 protein
CTD
PMID:21514314
NCBI chr 1:198,192,773...198,198,975
Ensembl chr 1:198,192,773...198,198,975
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Msi1
musashi RNA-binding protein 1
decreases expression
ISO
eckol results in decreased expression of MSI1 protein
CTD
PMID:21514314
NCBI chr12:46,899,835...46,935,335
Ensembl chr12:46,895,447...46,920,952
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Nes
nestin
decreases expression
ISO
eckol results in decreased expression of NES protein
CTD
PMID:21514314
NCBI chr 2:187,343,109...187,352,972
Ensembl chr 2:187,344,056...187,352,969
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Prom1
prominin 1
decreases expression
ISO
eckol results in decreased expression of PROM1 protein
CTD
PMID:21514314
NCBI chr14:71,532,321...71,637,400
Ensembl chr14:71,533,063...71,637,417
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Raf1
Raf-1 proto-oncogene, serine/threonine kinase
decreases activity
ISO
eckol results in decreased activity of RAF1 protein
CTD
PMID:21514314
NCBI chr 4:147,532,040...147,592,769
Ensembl chr 4:147,532,042...147,592,699
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Sod2
superoxide dismutase 2
multiple interactions increases expression
ISO
eckol inhibits the reaction [Hydrogen Peroxide results in decreased expression of and results in decreased activity of SOD2 protein]; FOXO3 mutant form inhibits the reaction [eckol results in increased expression of SOD2 protein] eckol results in increased expression of SOD2 mRNA; eckol results in increased expression of SOD2 protein
CTD
PMID:24700636
NCBI chr 1:47,914,757...47,921,587
Ensembl chr 1:47,914,759...47,921,587
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Sox2
SRY-box transcription factor 2
decreases expression
ISO
eckol results in decreased expression of SOX2 protein
CTD
PMID:21514314
NCBI chr 2:121,165,137...121,167,545
Ensembl chr 2:121,165,137...121,167,545
Term paths to the root one shortest all shortest one longest all longest one shortest and longest all
Path 1
CHEBI ontology
19841
role
19792
biological role
19792
biochemical role
19328
metabolite
19308
eukaryotic metabolite
18965
algal metabolite
13636
phloroglucinol
44
(6R)-2-acetyl-6-(3-acetyl-2,4,6-trihydroxy-5-methylphenyl)-3-hydroxy-6-methylcyclohexa-2,4-dien-1-one
0
1-[(3-methylbutanoyl)phloroglucinyl]-beta-D-glucopyranoside
0
1-[(pentanoyl)-phloroglucinyl]-beta-D-glucopyranoside
0
2,4-diacetylphloroglucinol
0
2-acylphloroglucinol +
0
6,6'-bieckol
0
7-phloroeckol
0
Agrimophol
0
Aspidin
10
Aspidinol
0
Aspidinol D
0
Filixic acid BBB
0
Preremirol
0
Xanthoxylin
0
Yungensin D
0
Yungensin E
0
aspidinol C
0
dieckol
17
dihydrophloroglucinol
0
eckol +
13
eckstolonol
0
filicinic acid +
0
flamenol
0
flavaspidic acid AB
0
flavaspidic acid PB
0
fucodiphloroethol G
0
mallotophilippen A
0
mallotophilippen B
0
multifidol +
0
Path 2
CHEBI ontology
19841
subatomic particle
19839
composite particle
19839
hadron
19839
baryon
19839
nucleon
19839
atomic nucleus
19839
atom
19839
main group element atom
19732
p-block element atom
19732
chalcogen
19425
oxygen atom
19387
oxygen molecular entity
19387
hydroxides
19113
organic hydroxy compound
18674
polyol
7818
triol
5978
benzenetriol
2548
phloroglucinol
44
(6R)-2-acetyl-6-(3-acetyl-2,4,6-trihydroxy-5-methylphenyl)-3-hydroxy-6-methylcyclohexa-2,4-dien-1-one
0
1-[(3-methylbutanoyl)phloroglucinyl]-beta-D-glucopyranoside
0
1-[(pentanoyl)-phloroglucinyl]-beta-D-glucopyranoside
0
2,4-diacetylphloroglucinol
0
2-acylphloroglucinol +
0
6,6'-bieckol
0
7-phloroeckol
0
Agrimophol
0
Aspidin
10
Aspidinol
0
Aspidinol D
0
Filixic acid BBB
0
Preremirol
0
Xanthoxylin
0
Yungensin D
0
Yungensin E
0
aspidinol C
0
dieckol
17
dihydrophloroglucinol
0
eckol +
13
eckstolonol
0
filicinic acid +
0
flamenol
0
flavaspidic acid AB
0
flavaspidic acid PB
0
fucodiphloroethol G
0
mallotophilippen A
0
mallotophilippen B
0
multifidol +
0