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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 3:55,480,024...55,587,946
Ensembl chr 3:55,480,024...55,587,946
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 1:263,554,426...263,612,556
Ensembl chr 1:263,554,453...263,613,252
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 chr15:103,695,415...103,927,980
Ensembl chr15:103,696,557...103,927,592
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 6:54,963,990...55,001,806
Ensembl chr 6:54,963,990...55,001,464
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 6:137,218,398...137,239,970
Ensembl chr 6:137,218,376...137,236,258
JBrowse link
G Bak1 BCL2-antagonist/killer 1 increases expression ISO chrysophanic acid results in increased expression of BAK1 protein CTD PMID:30300626 NCBI chr20:5,609,620...5,618,899
Ensembl chr20:5,609,625...5,618,260
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 1:101,451,801...101,457,207
Ensembl chr 1:101,451,802...101,457,207
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 8:62,472,087...62,478,122
Ensembl chr 8:62,472,095...62,478,147
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 8:62,451,360...62,458,244
Ensembl chr 8:62,451,329...62,458,301
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 6:2,308,179...2,316,739
Ensembl chr 6:2,307,808...2,316,722
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 1:83,163,103...83,236,615
Ensembl chr 1:83,163,079...83,236,615
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 5:19,358,734...19,368,431
Ensembl chr 5:19,358,734...19,368,431
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 8:130,548,418...130,550,388
Ensembl chr 8:130,548,418...130,550,388
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 7:70,578,564...70,585,074
Ensembl chr 7:70,580,198...70,585,084
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 4:98,648,513...98,709,695
Ensembl chr 4:98,648,545...98,709,694
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 6:102,048,372...102,073,041
Ensembl chr 6:102,048,372...102,073,041
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 chr10:94,588,555...94,682,072
Ensembl chr10:94,588,555...94,681,914
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 chr11:88,203,863...88,273,301
Ensembl chr11:88,211,599...88,273,254
JBrowse link
G Mapk14 mitogen activated protein kinase 14 affects phosphorylation ISO chrysophanic acid affects the phosphorylation of MAPK14 protein CTD PMID:30300626 NCBI chr20:5,933,290...5,995,137
Ensembl chr20:5,933,303...5,995,137
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 1:198,192,773...198,198,975
Ensembl chr 1:198,192,773...198,198,975
JBrowse link
G Mapk8 mitogen-activated protein kinase 8 affects phosphorylation ISO chrysophanic acid affects the phosphorylation of MAPK8 protein CTD PMID:30300626 NCBI chr16:9,620,854...9,709,342
Ensembl chr16:9,625,177...9,709,347
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 3:124,880,698...124,884,570
Ensembl chr 3:124,880,698...124,884,570
JBrowse link
G Rps6 ribosomal protein S6 decreases phosphorylation ISO chrysophanic acid results in decreased phosphorylation of RPS6 protein CTD PMID:30300626 NCBI chr 5:105,197,821...105,200,681
Ensembl chr 5:105,197,857...105,200,148
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 chr10:73,824,200...73,865,503
Ensembl chr10:73,824,202...73,865,364
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 6:104,617,730...104,631,355
Ensembl chr 6:104,617,730...104,631,355
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 1:224,824,809...224,833,284
Ensembl chr 1:224,824,799...224,833,259
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 1:224,799,444...224,818,482
Ensembl chr 1:224,800,252...224,818,482
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 1:198,100,586...198,104,106
Ensembl chr 1:198,100,586...198,104,109
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 9:95,161,157...95,302,822
Ensembl chr 9:95,161,157...95,302,822
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 8:62,451,360...62,458,244
Ensembl chr 8:62,451,329...62,458,301
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
          chrysophanol 29
            2-hydroxychrysophanol 1
            chrysophanol 8-O-beta-D-glucoside 0
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
                                          quinone 8338
                                            acenoquinone 7497
                                              anthraquinone 469
                                                hydroxyanthraquinones 461
                                                  dihydroxyanthraquinone 320
                                                    chrysazin 68
                                                      chrysophanol 29
                                                        2-hydroxychrysophanol 1
                                                        chrysophanol 8-O-beta-D-glucoside 0
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RGD is funded by grant HL64541 from the National Heart, Lung, and Blood Institute on behalf of the NIH.