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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:retinal
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Accession:CHEBI:15035 term browser browse the term
Definition:An enal that consists of 3,7-dimethyl-9-nona-2,4,6,8-tetraenal (double bond geometry unspecified) carrying a 2,6,6-trimethylcyclohex-1-en-1-yl group at the 9-position.
Synonyms:exact_synonym: 3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenal
 related_synonym: 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;   InChIKey=NCYCYZXNIZJOKI-UHFFFAOYSA-N;   SMILES=[H]C(=O)C=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C
 xref: MetaCyc:Retinals;   Reaxys:2055098


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13-cis-retinal term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Cyp3a2 cytochrome P450, family 3, subfamily a, polypeptide 2 multiple interactions
increases activity
ISO 13-cis-retinal promotes the reaction [[RXRA protein binds to NR1I2 protein] which results in increased expression of CYP3A4 mRNA]
13-cis-retinal results in increased activity of CYP3A4 protein
CTD PMID:16632523 NCBI chr12:9,207,986...9,230,038
Ensembl chr12:9,015,383...9,285,008
JBrowse link
G Nr1i2 nuclear receptor subfamily 1, group I, member 2 multiple interactions ISO 13-cis-retinal promotes the reaction [[RXRA protein binds to NR1I2 protein] which results in increased expression of CYP3A4 mRNA] CTD PMID:16632523 NCBI chr11:62,460,213...62,496,665
Ensembl chr11:62,460,213...62,496,658
JBrowse link
G Rxra retinoid X receptor alpha multiple interactions ISO 13-cis-retinal promotes the reaction [[RXRA protein binds to NR1I2 protein] which results in increased expression of CYP3A4 mRNA] CTD PMID:16632523 NCBI chr 3:10,989,832...11,076,366
Ensembl chr 3:10,989,832...11,073,712
JBrowse link
9-cis-retinal term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Akr1b10 aldo-keto reductase family 1 member B10 increases reduction ISO AKR1B10 protein results in increased reduction of 9-cis-retinal CTD PMID:21851338 NCBI chr 4:63,038,459...63,060,336
Ensembl chr 4:63,040,169...63,053,852
JBrowse link
G Akr1c1 aldo-keto reductase family 1, member C1 increases reduction ISO AKR1C4 protein results in increased reduction of 9-cis-retinal CTD PMID:21851338 NCBI chr17:65,810,474...65,837,385
Ensembl chr17:65,810,475...65,837,326
JBrowse link
G Akr1c3 aldo-keto reductase family 1, member C3 increases reduction ISO 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 chr17:66,110,970...66,127,867
Ensembl chr17:66,110,963...66,127,873
JBrowse link
G Aldh1a1 aldehyde dehydrogenase 1 family, member A1 affects oxidation
multiple interactions
EXP
ISO
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 1:218,000,470...218,152,962
Ensembl chr 1:218,042,127...218,152,961
JBrowse link
G Cyp3a2 cytochrome P450, family 3, subfamily a, polypeptide 2 increases activity
multiple interactions
ISO 9-cis-retinal results in increased activity of CYP3A4 protein
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 chr12:9,207,986...9,230,038
Ensembl chr12:9,015,383...9,285,008
JBrowse link
G Mitf melanocyte inducing transcription factor increases expression
multiple interactions
ISO 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 4:130,409,020...130,621,145
Ensembl chr 4:130,409,217...130,621,145
JBrowse link
G Nr1i2 nuclear receptor subfamily 1, group I, member 2 multiple interactions ISO 9-cis-retinal promotes the reaction [[RXRA protein binds to NR1I2 protein] which results in increased expression of CYP3A4 mRNA] CTD PMID:16632523 NCBI chr11:62,460,213...62,496,665
Ensembl chr11:62,460,213...62,496,658
JBrowse link
G Nr1i3 nuclear receptor subfamily 1, group I, member 3 multiple interactions ISO 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 chr13:83,632,940...83,638,193
Ensembl chr13:83,632,899...83,637,906
JBrowse link
G RGD1564865 similar to 20-alpha-hydroxysteroid dehydrogenase increases reduction ISO AKR1C1 protein results in increased reduction of 9-cis-retinal CTD PMID:21851338 NCBI chr17:65,847,580...65,881,488
Ensembl chr17:65,835,634...65,881,488
JBrowse link
G Rxra retinoid X receptor alpha multiple interactions ISO 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 3:10,989,832...11,076,366
Ensembl chr 3:10,989,832...11,073,712
JBrowse link
G Tyr tyrosinase increases expression
multiple interactions
ISO 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 chr 1:141,115,036...141,210,207
Ensembl chr 1:141,115,036...141,210,207
JBrowse link
all-trans-4-oxoretinal term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Akr1b1 aldo-keto reductase family 1 member B increases reduction ISO AKR1B1 protein results in increased reduction of 4-oxoretinaldehyde CTD PMID:19014918 NCBI chr 4:62,932,033...62,946,126
Ensembl chr 4:62,932,031...62,946,157
JBrowse link
G Akr1b10 aldo-keto reductase family 1 member B10 increases reduction ISO AKR1B10 protein results in increased reduction of 4-oxoretinaldehyde CTD PMID:19014918 NCBI chr 4:63,038,459...63,060,336
Ensembl chr 4:63,040,169...63,053,852
JBrowse link
all-trans-retinal term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Abca4 ATP binding cassette subfamily A member 4 affects transport ISO ABCA4 protein affects the transport of Retinaldehyde CTD PMID:16968212 NCBI chr 2:210,164,813...210,302,069
Ensembl chr 2:210,164,813...210,302,069
JBrowse link
G Adh4 alcohol dehydrogenase 4 (class II), pi polypeptide increases metabolic processing EXP ADH4 protein results in increased metabolism of Retinaldehyde CTD PMID:17279314 NCBI chr 2:226,948,717...226,966,747 JBrowse link
G Akr1b1 aldo-keto reductase family 1 member B increases reduction ISO AKR1B1 protein results in increased reduction of Retinaldehyde CTD PMID:19014918 NCBI chr 4:62,932,033...62,946,126
Ensembl chr 4:62,932,031...62,946,157
JBrowse link
G Akr1b10 aldo-keto reductase family 1 member B10 increases reduction
increases metabolic processing
ISO AKR1B10 protein results in increased reduction of Retinaldehyde
AKR1B10 protein results in increased metabolism of Retinaldehyde
CTD PMID:19014918 PMID:21329680 NCBI chr 4:63,038,459...63,060,336
Ensembl chr 4:63,040,169...63,053,852
JBrowse link
G Akr1b7 aldo-keto reductase family 1, member B7 increases metabolic processing ISO AKR1B7 protein results in increased metabolism of Retinaldehyde CTD PMID:21329680 NCBI chr 4:63,053,560...63,100,934
Ensembl chr 4:63,076,800...63,089,502
JBrowse link
G Akr1c3 aldo-keto reductase family 1, member C3 increases reduction ISO AKR1C3 protein results in increased reduction of Retinaldehyde CTD PMID:23261716 NCBI chr17:66,110,970...66,127,867
Ensembl chr17:66,110,963...66,127,873
JBrowse link
G Alb albumin affects binding ISO Retinaldehyde binds to ALB protein CTD PMID:17217919 NCBI chr14:17,607,397...17,622,814
Ensembl chr14:17,607,381...17,622,836
JBrowse link
G Aldh1a1 aldehyde dehydrogenase 1 family, member A1 multiple interactions
affects oxidation
ISO
EXP
[ALDH1A1 protein co-treated with NAD] results in increased oxidation of Retinaldehyde; ALDH1A1 protein affects the metabolism of [RBP1 protein binds to Retinaldehyde]; ALDH1A1 protein binds to and results in increased oxidation of Retinaldehyde
ALDH1A1 protein affects the oxidation of Retinaldehyde
Magnesium Chloride inhibits the reaction [ALDH1A1 protein affects the oxidation of Retinaldehyde]; Magnesium inhibits the reaction [ALDH1A1 protein affects the oxidation of Retinaldehyde]
CTD PMID:10559215 PMID:17167544 PMID:23220587 NCBI chr 1:218,000,470...218,152,962
Ensembl chr 1:218,042,127...218,152,961
JBrowse link
G Aldh1a2 aldehyde dehydrogenase 1 family, member A2 multiple interactions EXP ALDH1A2 protein binds to and results in increased oxidation of Retinaldehyde CTD PMID:23220587 NCBI chr 8:71,877,850...71,957,107
Ensembl chr 8:71,877,850...71,957,107
JBrowse link
G Aldh1a3 aldehyde dehydrogenase 1 family, member A3 increases oxidation ISO ALDH1A3 protein results in increased oxidation of Retinaldehyde CTD PMID:17526768 NCBI chr 1:119,982,272...120,017,416
Ensembl chr 1:119,982,277...120,017,436
JBrowse link
G Aldh2 aldehyde dehydrogenase 2 family member multiple interactions
increases metabolic processing
ISO [ALDH2 protein co-treated with NAD] results in increased oxidation of Retinaldehyde
ALDH2 protein results in increased metabolism of Retinaldehyde
CTD PMID:10559215 PMID:11744614 NCBI chr12:34,949,549...34,982,527 JBrowse link
G Aldh3a1 aldehyde dehydrogenase 3 family, member A1 increases activity EXP Retinaldehyde results in increased activity of ALDH3A1 protein CTD PMID:17126819 NCBI chr10:45,892,993...45,902,680
Ensembl chr10:45,892,924...45,902,681
JBrowse link
G Areg amphiregulin increases expression ISO Retinaldehyde results in increased expression of AREG mRNA CTD PMID:16470170 NCBI chr14:16,972,185...16,981,443
Ensembl chr14:16,972,187...16,981,535
JBrowse link
G Atf4 activating transcription factor 4 increases expression ISO Retinaldehyde results in increased expression of ATF4 mRNA CTD PMID:25331497 NCBI chr 7:111,804,135...111,806,457
Ensembl chr 7:111,804,183...111,806,446
JBrowse link
G Btc betacellulin decreases expression ISO Retinaldehyde results in decreased expression of BTC mRNA CTD PMID:16470170 NCBI chr14:16,708,447...16,746,961
Ensembl chr14:16,707,982...16,747,049
JBrowse link
G Casp3 caspase 3 increases activity ISO Retinaldehyde results in increased activity of CASP3 protein CTD PMID:25331497 NCBI chr16:45,662,910...45,681,171
Ensembl chr16:45,662,910...45,684,648
JBrowse link
G Cyp26a1 cytochrome P450, family 26, subfamily a, polypeptide 1 multiple interactions
increases expression
ISO [Retinaldehyde co-treated with Dihydrotestosterone] results in increased expression of CYP26A1 mRNA
Retinaldehyde results in increased expression of CYP26A1 mRNA
CTD PMID:17526768 NCBI chr 1:235,471,368...235,475,204
Ensembl chr 1:235,471,298...235,475,204
JBrowse link
G Ddit3 DNA-damage inducible transcript 3 increases expression ISO Retinaldehyde results in increased expression of DDIT3 mRNA CTD PMID:25331497 NCBI chr 7:63,115,645...63,121,203
Ensembl chr 7:63,116,380...63,121,201
JBrowse link
G Dhrs4 dehydrogenase/reductase 4 increases reduction ISO DHRS4 protein results in increased reduction of Retinaldehyde CTD PMID:12680773 NCBI chr15:28,966,544...28,978,135
Ensembl chr15:28,966,553...28,978,127
JBrowse link
G Gclc glutamate-cysteine ligase, catalytic subunit increases expression ISO Retinaldehyde results in increased expression of GCLC mRNA CTD PMID:25331497 PMID:27751755 NCBI chr 8:78,629,899...78,668,547
Ensembl chr 8:78,630,127...78,668,544
JBrowse link
G Hbegf heparin-binding EGF-like growth factor increases expression ISO Retinaldehyde results in increased expression of HBEGF mRNA CTD PMID:16470170 NCBI chr18:28,106,284...28,116,167
Ensembl chr18:28,105,760...28,116,441
JBrowse link
G Hmox1 heme oxygenase 1 increases expression ISO Retinaldehyde results in increased expression of HMOX1 mRNA CTD PMID:25331497 PMID:27751755 NCBI chr19:13,466,287...13,474,082
Ensembl chr19:13,467,244...13,474,079
JBrowse link
G Hspa5 heat shock protein family A (Hsp70) member 5 increases expression ISO Retinaldehyde results in increased expression of HSPA5 protein CTD PMID:25331497 NCBI chr 3:18,055,507...18,059,969
Ensembl chr 3:18,055,405...18,059,891
JBrowse link
G Nfe2l2 nuclear factor, erythroid 2-like 2 increases expression ISO Retinaldehyde results in increased expression of NFE2L2 mRNA CTD PMID:25331497 PMID:27751755 NCBI chr 3:60,594,239...60,621,785
Ensembl chr 3:60,594,242...60,621,737
JBrowse link
G Parp1 poly (ADP-ribose) polymerase 1 increases cleavage ISO Retinaldehyde results in increased cleavage of PARP1 protein CTD PMID:25331497 NCBI chr13:92,307,593...92,339,406
Ensembl chr13:92,307,586...92,339,404
JBrowse link
G Ppargc1a PPARG coactivator 1 alpha increases expression ISO Retinaldehyde results in increased expression of PPARGC1A mRNA CTD PMID:23056435 NCBI chr14:58,860,752...59,516,525
Ensembl chr14:58,861,144...59,512,656
JBrowse link
G Ppp1r15a protein phosphatase 1, regulatory subunit 15A increases expression ISO Retinaldehyde results in increased expression of PPP1R15A mRNA CTD PMID:25331497 NCBI chr 1:96,000,053...96,003,128
Ensembl chr 1:96,000,058...96,003,171
JBrowse link
G Rbp1 retinol binding protein 1 multiple interactions ISO ALDH1A1 protein affects the metabolism of [RBP1 protein binds to Retinaldehyde] CTD PMID:10559215 NCBI chr 8:99,025,218...99,046,740
Ensembl chr 8:99,025,206...99,046,743
JBrowse link
G Rdh10 retinol dehydrogenase 10 increases chemical synthesis ISO RDH10 protein results in increased chemical synthesis of Retinaldehyde CTD PMID:17473173 NCBI chr 5:3,186,671...3,215,572
Ensembl chr 5:3,188,445...3,215,572
JBrowse link
G Rdh12 retinol dehydrogenase 12 increases metabolic processing ISO RDH12 protein results in increased metabolism of Retinaldehyde CTD PMID:16269441 NCBI chr 6:98,015,465...98,028,388
Ensembl chr 6:98,015,465...98,028,388
JBrowse link
G Rdh5 retinol dehydrogenase 5 increases chemical synthesis ISO RDH5 protein results in increased chemical synthesis of Retinaldehyde CTD PMID:16968212 NCBI chr 7:1,340,545...1,347,361 JBrowse link
G Rpe65 retinoid isomerohydrolase RPE65 increases chemical synthesis
increases metabolic processing
multiple interactions
ISO
EXP
RPE65 protein results in increased chemical synthesis of Retinaldehyde
RPE65 protein results in increased metabolism of Retinaldehyde
[13,17,21-trimethyldocosa-12,16,20-trien-11-one binds to and results in decreased activity of RPE65 protein] which results in decreased abundance of Retinaldehyde; [3,7,11-trimethyldodeca-2,6,10-trienoic acid hexadecylamide binds to and results in decreased activity of RPE65 protein] which results in decreased abundance of Retinaldehyde; [Isotretinoin binds to and results in decreased activity of RPE65 protein] which results in decreased abundance of Retinaldehyde
[13,17,21-trimethyldocosa-12,16,20-trien-11-one binds to and results in decreased activity of RPE65 protein] which results in decreased abundance of Retinaldehyde; [3,7,11-trimethyldodeca-2,6,10-trienoic acid hexadecylamide binds to and results in decreased activity of RPE65 protein] which results in decreased abundance of Retinaldehyde; [Isotretinoin binds to and results in decreased activity of RPE65 protein] which results in decreased abundance of Retinaldehyde; Retinaldehyde inhibits the reaction [RPE65 exon mutant form results in decreased uptake of Manganese]
CTD PMID:16026160 PMID:16411761 PMID:16828753 PMID:17251447 PMID:19060264 NCBI chr 2:248,766,497...248,798,403
Ensembl chr 2:248,766,612...248,798,403
JBrowse link
G Sdr16c5 short chain dehydrogenase/reductase family 16C, member 5 increases reduction
increases chemical synthesis
ISO SDR16C5 protein results in increased reduction of Retinaldehyde
SDR16C5 protein results in increased chemical synthesis of Retinaldehyde
CTD PMID:18926804 PMID:27793605 NCBI chr 5:17,018,813...17,043,974
Ensembl chr 5:17,018,813...17,040,970
JBrowse link

Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19812
    role 19761
      application 19471
        solvent 16635
          formic acid 8814
            formyl group 8786
              aldehyde 8786
                retinals 41
                  retinal 41
                    11-cis-retinal + 0
                    13-cis-retinal 3
                    9-cis-retinal 11
                    all-trans-retinal + 33
Path 2
Term Annotations click to browse term
  CHEBI ontology 19812
    subatomic particle 19811
      composite particle 19811
        hadron 19811
          baryon 19811
            nucleon 19811
              atomic nucleus 19811
                atom 19811
                  main group element atom 19708
                    p-block element atom 19708
                      carbon group element atom 19630
                        carbon atom 19620
                          organic molecular entity 19620
                            organic group 18728
                              organic divalent group 18719
                                organodiyl group 18719
                                  carbonyl group 18667
                                    carbonyl compound 18667
                                      carboxylic acid 18364
                                        carboacyl group 17482
                                          univalent carboacyl group 17482
                                            formyl group 8786
                                              aldehyde 8786
                                                alpha,beta-unsaturated aldehyde 2890
                                                  enal 2890
                                                    retinal 41
                                                      11-cis-retinal + 0
                                                      13-cis-retinal 3
                                                      9-cis-retinal 11
                                                      all-trans-retinal + 33
paths to the root