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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: 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 PMID:33438235 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 chr12:9,207,978...9,230,064
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
Ensembl chr 9:88,713,184...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 chr12:9,207,978...9,230,064
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 19880
    role 19850
      application 19695
        anti-inflammatory agent 16672
          chrysophanol 30
            2-hydroxychrysophanol 2
            chrysophanol 8-O-beta-D-glucoside 0
Path 2
Term Annotations click to browse term
  CHEBI ontology 19880
    subatomic particle 19878
      composite particle 19878
        hadron 19878
          baryon 19878
            nucleon 19878
              atomic nucleus 19878
                atom 19878
                  main group element atom 19817
                    p-block element atom 19817
                      carbon group element atom 19757
                        carbon atom 19754
                          organic molecular entity 19754
                            heteroorganic entity 19512
                              organochalcogen compound 19275
                                organooxygen compound 19191
                                  carbonyl compound 18914
                                    ketone 17263
                                      cyclic ketone 15911
                                        quinone 9903
                                          acenoquinone 7725
                                            anthraquinone 518
                                              hydroxyanthraquinones 506
                                                dihydroxyanthraquinone 354
                                                  chrysazin 73
                                                    chrysophanol 30
                                                      2-hydroxychrysophanol 2
                                                      chrysophanol 8-O-beta-D-glucoside 0
paths to the root