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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:chrysophanol
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Accession:CHEBI:3687 term browser browse the term
Definition:A trihydroxyanthraquinone that is chrysazin with a methyl substituent at C-3. It has been isolated from Aloe vera and exhibits antiviral and anti-inflammatory activity.
Synonyms:exact_synonym: 1,8-dihydroxy-3-methyl-9,10-anthraquinone
 related_synonym: 1,8-Dihydroxy-3-methylanthraquinone;   1,8-dihydroxy-3-methyl-9,10-anthracenedione;   3-methylchrysazin;   Chrysophanic acid;   Chrysophansaeure;   Formula=C15H10O4;   InChI=1S/C15H10O4/c1-7-5-9-13(11(17)6-7)15(19)12-8(14(9)18)3-2-4-10(12)16/h2-6,16-17H,1H3;   InChIKey=LQGUBLBATBMXHT-UHFFFAOYSA-N;   SMILES=Cc1cc(O)c2C(=O)c3c(O)cccc3C(=O)c2c1
 xref: Beilstein:1252300;   CAS:481-74-3;   Gmelin:220618;   HMDB:HMDB0030670;   KEGG:C10315;   KNApSAcK:C00000568;   LINCS:LSM-19027;   LIPID_MAPS_instance:LMPK13040006
 xref_mesh: MESH:C027113
 xref: MetaCyc:CPD-8216;   PMID:19742131;   PMID:24136708;   PMID:24358188;   PMID:24395532;   Reaxys:1252300;   Wikipedia:Chrysophanol


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chrysophanol term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Abcb11 ATP binding cassette subfamily B member 11 decreases expression EXP chrysophanic acid results in decreased expression of ABCB11 mRNA; chrysophanic acid results in decreased expression of ABCB11 protein CTD PMID:28161596 NCBI chr 3:54,016,854...54,112,797
Ensembl chr 3:54,017,127...54,112,730
JBrowse link
G Abcc2 ATP binding cassette subfamily C member 2 increases expression EXP chrysophanic acid results in increased expression of ABCC2 mRNA; chrysophanic acid results in increased expression of ABCC2 protein CTD PMID:28161596 NCBI chr 1:242,664,657...242,723,239
Ensembl chr 1:242,664,657...242,723,238
JBrowse link
G Abcc4 ATP binding cassette subfamily C member 4 increases expression EXP chrysophanic acid results in increased expression of ABCC4 mRNA; chrysophanic acid results in increased expression of ABCC4 protein CTD PMID:28161596 NCBI chr15:95,541,186...95,774,898
Ensembl chr15:95,542,315...95,774,283
JBrowse link
G Ahr aryl hydrocarbon receptor multiple interactions ISO chrysophanic acid inhibits the reaction [Tetrachlorodibenzodioxin results in increased activity of AHR protein] CTD PMID:19269596 NCBI chr 6:52,234,089...52,271,568
Ensembl chr 6:52,234,089...52,271,568
JBrowse link
G Akt1 AKT serine/threonine kinase 1 decreases phosphorylation ISO chrysophanic acid results in decreased phosphorylation of AKT1 protein CTD PMID:30300626 NCBI chr 6:131,713,716...131,735,319
Ensembl chr 6:131,713,720...131,733,921
JBrowse link
G Bak1 BCL2-antagonist/killer 1 increases expression ISO chrysophanic acid results in increased expression of BAK1 protein CTD PMID:30300626 NCBI chr20:5,100,480...5,109,669
Ensembl chr20:5,100,480...5,109,264
JBrowse link
G Bax BCL2 associated X, apoptosis regulator increases expression ISO chrysophanic acid results in increased expression of BAX protein CTD PMID:30300626 NCBI chr 1:95,940,001...95,945,407
Ensembl chr 1:95,938,808...95,945,368
JBrowse link
G Cyp1a1 cytochrome P450, family 1, subfamily a, polypeptide 1 decreases activity ISO chrysophanic acid results in decreased activity of CYP1A1 protein CTD PMID:27633141 NCBI chr 8:58,096,021...58,102,130
Ensembl chr 8:58,096,077...58,102,125
JBrowse link
G Cyp1a2 cytochrome P450, family 1, subfamily a, polypeptide 2 decreases activity
multiple interactions
increases metabolic processing
ISO chrysophanic acid results in decreased activity of CYP1A2 protein
[CYP1A2 protein results in increased metabolism of chrysophanic acid] which results in increased chemical synthesis of 2-hydroxychrysophanol
CTD PMID:27633141 PMID:29698620 NCBI chr 8:58,075,367...58,082,255
Ensembl chr 8:58,075,367...58,082,312
JBrowse link
G Cyp1b1 cytochrome P450, family 1, subfamily b, polypeptide 1 decreases activity ISO chrysophanic acid results in decreased activity of CYP1B1 protein CTD PMID:27633141 NCBI chr 6:15,342,312...15,350,886
Ensembl chr 6:15,342,344...15,350,917
JBrowse link
G Cyp2b3 cytochrome P450, family 2, subfamily b, polypeptide 3 multiple interactions
increases metabolic processing
ISO [CYP2B6 protein results in increased metabolism of chrysophanic acid] which results in increased chemical synthesis of aloe emodin CTD PMID:29698620 NCBI chr 1:81,652,762...81,732,153
Ensembl chr 1:81,652,787...81,732,143
JBrowse link
G Cyp3a2 cytochrome P450, family 3, subfamily a, polypeptide 2 increases metabolic processing
increases chemical synthesis
multiple interactions
ISO CYP3A4 protein results in increased metabolism of chrysophanic acid
CYP3A4 protein results in increased chemical synthesis of chrysophanic acid metabolite
[CYP3A4 protein results in increased metabolism of chrysophanic acid] which results in increased chemical synthesis of 2-hydroxychrysophanol; [CYP3A4 protein results in increased metabolism of chrysophanic acid] which results in increased chemical synthesis of aloe emodin
CTD PMID:29698620 NCBI chr12:9,207,986...9,230,038
Ensembl chr12:9,015,383...9,285,008
JBrowse link
G Cyp7a1 cytochrome P450 family 7 subfamily A member 1 increases expression EXP chrysophanic acid results in increased expression of CYP7A1 mRNA; chrysophanic acid results in increased expression of CYP7A1 protein CTD PMID:28161596 NCBI chr 5:19,376,979...19,386,676
Ensembl chr 5:19,376,974...19,386,688
JBrowse link
G Cyp8b1 cytochrome P450 family 8 subfamily B member 1 decreases expression EXP chrysophanic acid results in decreased expression of CYP8B1 mRNA; chrysophanic acid results in decreased expression of CYP8B1 protein CTD PMID:28161596 NCBI chr 8:121,578,123...121,580,093
Ensembl chr 8:121,557,062...121,580,166
JBrowse link
G Ddit3 DNA-damage inducible transcript 3 increases expression ISO chrysophanic acid results in increased expression of DDIT3 protein CTD PMID:30300626 NCBI chr 7:63,115,645...63,121,203
Ensembl chr 7:63,116,380...63,121,201
JBrowse link
G Eif2ak3 eukaryotic translation initiation factor 2 alpha kinase 3 increases phosphorylation
multiple interactions
ISO chrysophanic acid results in increased phosphorylation of EIF2AK3 protein
Acetylcysteine inhibits the reaction [chrysophanic acid results in increased phosphorylation of EIF2AK3 protein]
CTD PMID:30300626 NCBI chr 4:102,805,495...102,866,914
Ensembl chr 4:102,805,510...102,866,911
JBrowse link
G Eif2s1 eukaryotic translation initiation factor 2 subunit alpha increases phosphorylation
multiple interactions
ISO chrysophanic acid results in increased phosphorylation of EIF2S1 protein
Acetylcysteine inhibits the reaction [chrysophanic acid results in increased phosphorylation of EIF2S1 protein]
CTD PMID:30300626 NCBI chr 6:97,672,829...97,697,499
Ensembl chr 6:97,672,766...97,706,225
JBrowse link
G Ern1 endoplasmic reticulum to nucleus signaling 1 increases expression ISO chrysophanic acid results in increased expression of ERN1 protein CTD PMID:30300626 NCBI chr10:91,326,889...91,421,201
Ensembl chr10:91,330,654...91,421,029
JBrowse link
G Mapk1 mitogen activated protein kinase 1 decreases phosphorylation ISO chrysophanic acid results in decreased phosphorylation of MAPK1 protein CTD PMID:30300626 NCBI chr11:83,957,813...84,023,629
Ensembl chr11:83,957,813...84,023,616
JBrowse link
G Mapk14 mitogen activated protein kinase 14 affects phosphorylation ISO chrysophanic acid affects the phosphorylation of MAPK14 protein CTD PMID:30300626 NCBI chr20:6,749,646...6,810,590
Ensembl chr20:6,749,670...6,810,589
JBrowse link
G Mapk3 mitogen activated protein kinase 3 decreases phosphorylation ISO chrysophanic acid results in decreased phosphorylation of MAPK3 protein CTD PMID:30300626 NCBI chr 1:181,366,646...181,372,863
Ensembl chr 1:181,366,637...181,372,863
JBrowse link
G Mapk8 mitogen-activated protein kinase 8 affects phosphorylation ISO chrysophanic acid affects the phosphorylation of MAPK8 protein CTD PMID:30300626 NCBI chr16:8,638,897...8,721,960
Ensembl chr16:8,638,924...8,721,981
JBrowse link
G Pcna proliferating cell nuclear antigen decreases expression ISO chrysophanic acid results in decreased expression of PCNA protein CTD PMID:30300626 NCBI chr 3:119,499,039...119,502,911
Ensembl chr 3:119,498,810...119,502,995
JBrowse link
G Rps6 ribosomal protein S6 decreases phosphorylation ISO chrysophanic acid results in decreased phosphorylation of RPS6 protein CTD PMID:30300626 NCBI chr 5:101,371,716...101,374,576
Ensembl chr 5:101,371,136...101,374,602
Ensembl chr 5:101,371,136...101,374,602
JBrowse link
G Rps6kb1 ribosomal protein S6 kinase B1 decreases phosphorylation ISO chrysophanic acid results in decreased phosphorylation of RPS6KB1 protein CTD PMID:30300626 NCBI chr10:71,323,777...71,367,908
Ensembl chr10:71,323,777...71,367,908
JBrowse link
G Slc10a1 solute carrier family 10 member 1 decreases expression EXP chrysophanic acid results in decreased expression of SLC10A1 mRNA; chrysophanic acid results in decreased expression of SLC10A1 protein CTD PMID:28161596 NCBI chr 6:100,613,045...100,626,670
Ensembl chr 6:100,613,045...100,626,670
JBrowse link
G Slc22a6 solute carrier family 22 member 6 decreases activity ISO chrysophanic acid results in decreased activity of SLC22A6 protein CTD PMID:29045746 NCBI chr 1:205,522,579...205,531,179
Ensembl chr 1:205,522,729...205,531,173
JBrowse link
G Slc22a8 solute carrier family 22 member 8 decreases activity ISO chrysophanic acid results in decreased activity of SLC22A8 protein CTD PMID:29045746 NCBI chr 1:205,496,331...205,516,378
Ensembl chr 1:205,498,084...205,517,450
JBrowse link
G Sult1a1 sulfotransferase family 1A member 1 decreases activity ISO chrysophanic acid results in decreased activity of SULT1A1 protein CTD PMID:27633141 NCBI chr 1:181,272,022...181,276,750
Ensembl chr 1:181,272,023...181,275,562
JBrowse link
G Ugt1a9 UDP glucuronosyltransferase family 1 member A9 increases glucuronidation ISO UGT1A9 protein results in increased glucuronidation of chrysophanic acid CTD PMID:24854283 NCBI chr 9:88,696,981...88,808,465 JBrowse link
2-hydroxychrysophanol term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Cyp1a2 cytochrome P450, family 1, subfamily a, polypeptide 2 increases chemical synthesis
multiple interactions
ISO CYP1A2 protein results in increased chemical synthesis of 2-hydroxychrysophanol
[CYP1A2 protein results in increased metabolism of chrysophanic acid] which results in increased chemical synthesis of 2-hydroxychrysophanol
CTD PMID:29698620 NCBI chr 8:58,075,367...58,082,255
Ensembl chr 8:58,075,367...58,082,312
JBrowse link
G Cyp3a2 cytochrome P450, family 3, subfamily a, polypeptide 2 multiple interactions
increases chemical synthesis
ISO [CYP3A4 protein results in increased metabolism of chrysophanic acid] which results in increased chemical synthesis of 2-hydroxychrysophanol
CYP3A4 protein results in increased chemical synthesis of 2-hydroxychrysophanol
CTD PMID:29698620 NCBI chr12:9,207,986...9,230,038
Ensembl chr12:9,015,383...9,285,008
JBrowse link

Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19821
    role 19769
      application 19481
        anti-inflammatory agent 15831
          chrysophanol 30
            2-hydroxychrysophanol 2
            chrysophanol 8-O-beta-D-glucoside 0
Path 2
Term Annotations click to browse term
  CHEBI ontology 19821
    subatomic particle 19819
      composite particle 19819
        hadron 19819
          baryon 19819
            nucleon 19819
              atomic nucleus 19819
                atom 19819
                  main group element atom 19716
                    p-block element atom 19716
                      carbon group element atom 19640
                        carbon atom 19630
                          organic molecular entity 19630
                            organic group 18737
                              organic divalent group 18728
                                organodiyl group 18728
                                  carbonyl group 18675
                                    carbonyl compound 18675
                                      ketone 16923
                                        cyclic ketone 15391
                                          quinone 8379
                                            acenoquinone 7512
                                              anthraquinone 475
                                                hydroxyanthraquinones 465
                                                  dihydroxyanthraquinone 321
                                                    chrysazin 69
                                                      chrysophanol 30
                                                        2-hydroxychrysophanol 2
                                                        chrysophanol 8-O-beta-D-glucoside 0
paths to the root