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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 3:74,424,620...74,520,646
Ensembl chr 3:74,424,979...74,520,581 		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 1:252,613,875...252,672,459
Ensembl chr 1:252,614,017...252,673,471 		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 chr15:101,948,387...102,182,912
Ensembl chr15:101,949,433...102,181,375 		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 6:57,961,423...57,998,901
Ensembl chr 6:57,961,423...57,998,901 		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 6:137,534,810...137,555,131
Ensembl chr 6:137,535,390...137,552,610 		JBrowse link
G Bak1 BCL2-antagonist/killer 1 increases expression ISO chrysophanic acid results in increased expression of BAK1 protein CTD PMID:30300626 NCBI chr20:5,102,334...5,111,615
Ensembl chr20:5,102,335...5,110,974 		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 1:105,076,472...105,081,906
Ensembl chr 1:105,076,473...105,086,429 		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 8:66,991,940...66,998,014
Ensembl chr 8:66,991,970...66,998,012 		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 8:66,971,261...66,978,149
Ensembl chr 8:66,971,261...66,978,149 		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 6:21,093,927...21,103,091
Ensembl chr 6:21,078,146...21,103,142 		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 1:90,780,468...90,859,852 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 chr12:14,321,771...14,343,886
Ensembl chr12:14,321,771...14,343,857 		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 5:24,174,505...24,184,202
Ensembl chr 5:24,174,505...24,184,202 		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 8:130,455,622...130,457,592
Ensembl chr 8:130,442,503...130,457,689 		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 7:65,001,695...65,006,517
Ensembl chr 7:65,005,501...65,006,509 		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 4:104,363,838...104,425,271
Ensembl chr 4:104,363,833...104,425,268 		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 6:103,405,880...103,430,549
Ensembl chr 6:103,405,788...103,431,649 		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 chr10:91,826,663...91,920,976
Ensembl chr10:91,830,428...91,920,791 		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 chr11:97,462,025...97,529,193
Ensembl chr11:97,462,025...97,527,825 		JBrowse link
G Mapk14 mitogen activated protein kinase 14 affects phosphorylation ISO chrysophanic acid affects the phosphorylation of MAPK14 protein CTD PMID:30300626 NCBI chr20:6,751,288...6,812,294
Ensembl chr20:6,751,357...6,812,294 		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 1:190,797,189...190,803,411
Ensembl chr 1:190,797,185...190,803,411 		JBrowse link
G Mapk8 mitogen-activated protein kinase 8 affects phosphorylation ISO chrysophanic acid affects the phosphorylation of MAPK8 protein CTD PMID:30300626 NCBI chr16:8,645,171...8,728,225
Ensembl chr16:8,645,198...8,728,427 		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 3:139,951,948...139,955,820
Ensembl chr 3:139,951,941...139,955,901 		JBrowse link
G Rps6 ribosomal protein S6 decreases phosphorylation ISO chrysophanic acid results in decreased phosphorylation of RPS6 protein CTD PMID:30300626 NCBI chr 5:106,417,680...106,420,540
Ensembl chr 5:106,417,680...106,420,566 		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 chr10:71,817,794...71,865,211
Ensembl chr10:71,815,614...71,865,238 		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 6:106,344,319...106,357,944
Ensembl chr 6:106,344,319...106,357,944 		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 1:214,951,493...214,960,317
Ensembl chr 1:214,951,867...214,960,311 		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 1:214,925,506...214,945,516
Ensembl chr 1:214,925,508...214,946,588 		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 1:190,702,592...190,706,112
Ensembl chr 1:190,702,592...190,706,131 		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 9:96,144,786...96,256,264
Ensembl chr 9:96,144,786...96,256,264 		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 8:66,971,261...66,978,149
Ensembl chr 8:66,971,261...66,978,149 		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 chr12:14,321,771...14,343,886
Ensembl chr12:14,321,771...14,343,857 		JBrowse link
Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 20841
    role 20801
      application 20602
        anti-inflammatory agent 16819
          chrysophanol 30
            2-hydroxychrysophanol 2
            chrysophanol 8-O-beta-D-glucoside 0
Path 2
Term Annotations click to browse term
  CHEBI ontology 20841
    subatomic particle 20839
      composite particle 20839
        hadron 20839
          baryon 20839
            nucleon 20839
              atomic nucleus 20839
                atom 20839
                  main group element atom 20762
                    p-block element atom 20786
                      carbon group element atom 20695
                        carbon atom 20690
                          organic molecular entity 20690
                            heteroorganic entity 20202
                              organochalcogen compound 19889
                                organooxygen compound 19791
                                  carbonyl compound 19426
                                    ketone 17444
                                      cyclic ketone 16033
                                        quinone 9929
                                          acenoquinone 7771
                                            anthraquinone 529
                                              hydroxyanthraquinones 517
                                                dihydroxyanthraquinone 354
                                                  chrysazin 73
                                                    chrysophanol 30
                                                      2-hydroxychrysophanol 2
                                                      chrysophanol 8-O-beta-D-glucoside 0
paths to the root