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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:9-cis-retinal
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Accession:CHEBI:78273 term browser browse the term
Definition:A retinal in which the double bond at position 9 has cis configuration, whilst the remaining acyclic double bonds have trans configuration.
Synonyms:related_synonym: (2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenal;   (9cis)-retinal;   9-C-retinal;   9-cis-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenal;   9-cis-7,11,13-trans-retinal;   9-cis-retinaldehyde;   9-cis-vitamin A aldehyde;   Formula=C20H28O;   InChI=1S/C20H28O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,15H,7,10,14H2,1-5H3/b9-6+,12-11+,16-8-,17-13+;   InChIKey=NCYCYZXNIZJOKI-MKOSUFFBSA-N;   SMILES=C/C(/C=C/C=C(/C)\\C=C\\C1=C(C)CCCC1(C)C)=C\\C=O;   isoretinene A
 xref: CAS:514-85-2;   HMDB:HMDB0006218;   KEGG:C16681;   LIPID_MAPS_instance:LMPR01090017
 xref_mesh: MESH:C031390
 xref: MetaCyc:CPD-13536;   PMID:10064560;   PMID:10389637;   PMID:11882655;   PMID:17003450;   PMID:20837787;   PMID:22090313;   PMID:4750425;   Reaxys:1914180



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9-cis-retinal term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G ADH1B alcohol dehydrogenase 1B (class I), beta polypeptide increases metabolic processing EXP ADH1B protein results in increased metabolism of 9-cis-retinal CTD PMID:17279314 NCBI chr 4:99,304,971...99,321,401
Ensembl chr 4:99,304,971...99,321,401
JBrowse link
G AKR1B10 aldo-keto reductase family 1 member B10 increases reduction EXP AKR1B10 protein results in increased reduction of 9-cis-retinal CTD PMID:21851338 NCBI chr 7:134,527,567...134,541,412
Ensembl chr 7:134,527,567...134,541,412
JBrowse link
G AKR1C1 aldo-keto reductase family 1 member C1 increases reduction EXP AKR1C1 protein results in increased reduction of 9-cis-retinal CTD PMID:21851338 NCBI chr10:4,963,415...4,983,283
Ensembl chr10:4,963,253...4,983,283
JBrowse link
G AKR1C3 aldo-keto reductase family 1 member C3 increases reduction EXP AKR1C3 protein mutant form results in increased reduction of 9-cis-retinal; AKR1C3 protein results in increased reduction of 9-cis-retinal CTD PMID:21851338 NCBI chr10:5,048,781...5,107,686
Ensembl chr10:5,035,354...5,107,686
JBrowse link
G AKR1C4 aldo-keto reductase family 1 member C4 increases reduction EXP AKR1C4 protein results in increased reduction of 9-cis-retinal CTD PMID:21851338 NCBI chr10:5,196,837...5,218,949
Ensembl chr10:5,195,462...5,218,949
JBrowse link
G ALDH1A1 aldehyde dehydrogenase 1 family member A1 affects oxidation
multiple interactions
ISO
EXP
ALDH1A1 protein affects the oxidation of 9-cis-retinal
ALDH1A1 mutant form inhibits the reaction [9-cis-retinal results in increased expression of MITF mRNA]; ALDH1A1 mutant form inhibits the reaction [9-cis-retinal results in increased expression of TYR mRNA]
Magnesium Chloride inhibits the reaction [ALDH1A1 protein affects the oxidation of 9-cis-retinal]; Magnesium inhibits the reaction [ALDH1A1 protein affects the oxidation of 9-cis-retinal]
CTD PMID:17167544 PMID:23489423 NCBI chr 9:72,900,671...72,953,053
Ensembl chr 9:72,900,671...73,080,442
JBrowse link
G CYP3A4 cytochrome P450 family 3 subfamily A member 4 multiple interactions
increases activity
EXP 1,4-bis(2-(3,5-dichloropyridyloxy))benzene promotes the reaction [9-cis-retinal promotes the reaction [[RXRA protein binds to NR1I3 protein] which binds to CYP3A4 promoter]]; 9-cis-retinal promotes the reaction [1,4-bis(2-(3,5-dichloropyridyloxy))benzene promotes the reaction [[RXRA protein binds to NR1I3 protein] which binds to CYP3A4 promoter]]; 9-cis-retinal promotes the reaction [[RXRA protein binds to NR1I2 protein] which results in increased expression of CYP3A4 mRNA]; 9-cis-retinal promotes the reaction [[RXRA protein binds to NR1I3 protein] which binds to CYP3A4 promoter]
9-cis-retinal results in increased activity of CYP3A4 protein
CTD PMID:16632523 PMID:19686701 NCBI chr 7:99,756,967...99,784,184
Ensembl chr 7:99,756,960...99,784,248
JBrowse link
G MITF melanocyte inducing transcription factor increases expression
multiple interactions
EXP 9-cis-retinal results in increased expression of MITF mRNA
ALDH1A1 mutant form inhibits the reaction [9-cis-retinal results in increased expression of MITF mRNA]
CTD PMID:23489423 NCBI chr 3:69,739,464...69,968,332
Ensembl chr 3:69,739,456...69,968,336
JBrowse link
G NR1I2 nuclear receptor subfamily 1 group I member 2 multiple interactions EXP 9-cis-retinal promotes the reaction [[RXRA protein binds to NR1I2 protein] which results in increased expression of CYP3A4 mRNA] CTD PMID:16632523 NCBI chr 3:119,782,101...119,818,487
Ensembl chr 3:119,780,484...119,818,487
JBrowse link
G NR1I3 nuclear receptor subfamily 1 group I member 3 multiple interactions EXP 1,4-bis(2-(3,5-dichloropyridyloxy))benzene promotes the reaction [9-cis-retinal promotes the reaction [[RXRA protein binds to NR1I3 protein] which binds to CYP3A4 promoter]]; 9-cis-retinal promotes the reaction [1,4-bis(2-(3,5-dichloropyridyloxy))benzene promotes the reaction [[RXRA protein binds to NR1I3 protein] which binds to CYP3A4 promoter]]; 9-cis-retinal promotes the reaction [[RXRA protein binds to NR1I3 protein] which binds to CYP3A4 promoter] CTD PMID:19686701 NCBI chr 1:161,229,669...161,238,203
Ensembl chr 1:161,229,666...161,238,244
JBrowse link
G RXRA retinoid X receptor alpha multiple interactions EXP 1,4-bis(2-(3,5-dichloropyridyloxy))benzene promotes the reaction [9-cis-retinal promotes the reaction [[RXRA protein binds to NR1I3 protein] which binds to CYP3A4 promoter]]; 9-cis-retinal promotes the reaction [1,4-bis(2-(3,5-dichloropyridyloxy))benzene promotes the reaction [[RXRA protein binds to NR1I3 protein] which binds to CYP3A4 promoter]]; 9-cis-retinal promotes the reaction [[RXRA protein binds to NR1I2 protein] which results in increased expression of CYP3A4 mRNA]; 9-cis-retinal promotes the reaction [[RXRA protein binds to NR1I3 protein] which binds to CYP3A4 promoter] CTD PMID:16632523 PMID:19686701 NCBI chr 9:134,326,455...134,440,585
Ensembl chr 9:134,317,098...134,440,585
JBrowse link
G TYR tyrosinase increases expression
multiple interactions
EXP 9-cis-retinal results in increased expression of TYR mRNA
ALDH1A1 mutant form inhibits the reaction [9-cis-retinal results in increased expression of TYR mRNA]
CTD PMID:23489423 NCBI chr11:89,177,875...89,295,759
Ensembl chr11:89,177,875...89,295,759
JBrowse link

Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 26040
    role 25956
      application 25180
        solvent 18735
          formic acid 10010
            formyl group 9972
              aldehyde 9972
                retinals 42
                  retinal 42
                    9-cis-retinal 12
Path 2
Term Annotations click to browse term
  CHEBI ontology 26040
    subatomic particle 26015
      composite particle 26015
        hadron 26015
          baryon 26015
            nucleon 26015
              atomic nucleus 26015
                atom 26015
                  main group element atom 25840
                    p-block element atom 25840
                      carbon group element atom 25441
                        carbon atom 25399
                          organic molecular entity 25399
                            organic group 23608
                              organic divalent group 23569
                                organodiyl group 23569
                                  carbonyl group 23563
                                    carbonyl compound 23563
                                      carboxylic acid 22717
                                        carboacyl group 20066
                                          univalent carboacyl group 20066
                                            formyl group 9972
                                              aldehyde 9972
                                                alpha,beta-unsaturated aldehyde 3171
                                                  enal 3171
                                                    retinal 42
                                                      9-cis-retinal 12
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