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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 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 chr11:65,022,100...65,058,546
Ensembl chr11:65,022,100...65,058,545
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 3:6,272,560...6,295,354
Ensembl chr 3:6,211,789...6,295,908
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 4:61,813,265...61,830,371
Ensembl chr 4:61,771,970...61,828,657
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 chr17:69,441,253...69,460,334
Ensembl chr17:69,441,223...69,460,321
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 chr17:69,761,126...69,778,021
Ensembl chr17:69,761,118...69,778,021
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 1:238,222,689...238,264,381
Ensembl chr 1:238,222,521...238,264,330
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 4:130,172,484...130,425,496
Ensembl chr 4:130,172,727...130,425,532
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 chr11:65,022,100...65,058,546
Ensembl chr11:65,022,100...65,058,545
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 chr13:89,585,072...89,591,278
Ensembl chr13:89,586,283...89,591,277
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 3:6,272,560...6,295,354
Ensembl chr 3:6,211,789...6,295,908
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 1:151,012,598...151,106,802
Ensembl chr 1:151,012,598...151,106,802
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 4:61,706,866...61,720,959
Ensembl chr 4:61,706,864...61,720,956
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 4:61,813,265...61,830,371
Ensembl chr 4:61,771,970...61,828,657
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 2:225,645,539...225,783,288
Ensembl chr 2:225,645,568...225,783,287
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 2:243,702,035...243,720,063
Ensembl chr 2:243,700,784...243,740,899
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 4:61,706,866...61,720,959
Ensembl chr 4:61,706,864...61,720,956
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 4:61,813,265...61,830,371
Ensembl chr 4:61,771,970...61,828,657
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 4:61,850,256...61,879,733
Ensembl chr 4:61,850,348...61,862,526
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 chr17:69,761,126...69,778,021
Ensembl chr17:69,761,118...69,778,021
JBrowse link
G Alb albumin affects binding ISO Retinaldehyde binds to ALB protein CTD PMID:17217919 NCBI chr14:19,176,275...19,191,793
Ensembl chr14:19,176,277...19,191,863
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 1:238,222,689...238,264,381
Ensembl chr 1:238,222,521...238,264,330
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 8:77,640,234...77,719,488
Ensembl chr 8:77,640,222...77,719,489
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 1:127,302,920...127,337,828
Ensembl chr 1:127,301,128...127,337,882
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 chr12:40,466,418...40,498,813
Ensembl chr12:40,466,495...40,498,752
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 chr10:47,490,168...47,499,855
Ensembl chr10:47,490,153...47,499,876
JBrowse link
G Areg amphiregulin increases expression ISO Retinaldehyde results in increased expression of AREG mRNA CTD PMID:16470170 NCBI chr14:18,521,921...18,531,179
Ensembl chr14:18,521,930...18,531,179
JBrowse link
G Atf4 activating transcription factor 4 increases expression ISO Retinaldehyde results in increased expression of ATF4 mRNA CTD PMID:25331497 NCBI chr 7:121,480,723...121,482,781
Ensembl chr 7:121,480,723...121,482,772
JBrowse link
G Btc betacellulin decreases expression ISO Retinaldehyde results in decreased expression of BTC mRNA CTD PMID:16470170 NCBI chr14:18,231,854...18,270,621
Ensembl chr14:18,231,860...18,272,484
JBrowse link
G Casp3 caspase 3 increases activity ISO Retinaldehyde results in increased activity of CASP3 protein CTD PMID:25331497 NCBI chr16:48,845,011...48,863,249
Ensembl chr16:48,845,012...48,863,204
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 1:256,382,861...256,386,729
Ensembl chr 1:256,382,791...256,386,729
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 7:70,578,564...70,585,074
Ensembl chr 7:70,580,198...70,585,084
JBrowse link
G Dhrs4 dehydrogenase/reductase 4 increases reduction ISO DHRS4 protein results in increased reduction of Retinaldehyde CTD PMID:12680773 NCBI chr15:34,155,043...34,167,073
Ensembl chr15:34,155,504...34,167,072
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 8:85,059,051...85,097,471
Ensembl chr 8:85,059,051...85,097,468
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 chr18:29,330,302...29,340,185
Ensembl chr18:29,329,764...29,340,403
JBrowse link
G Hmox1 heme oxygenase 1 increases expression ISO Retinaldehyde results in increased expression of HMOX1 mRNA CTD PMID:25331497, PMID:27751755 NCBI chr19:14,508,634...14,515,455
Ensembl chr19:14,508,616...14,515,456
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 3:13,838,304...13,842,763
Ensembl chr 3:13,838,304...13,842,762
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 3:62,497,568...62,525,146
Ensembl chr 3:62,497,571...62,524,996
JBrowse link
G Parp1 poly (ADP-ribose) polymerase 1 increases cleavage ISO Retinaldehyde results in increased cleavage of PARP1 protein CTD PMID:25331497 NCBI chr13:98,857,255...98,889,444
Ensembl chr13:98,857,177...98,889,716
JBrowse link
G Ppargc1a PPARG coactivator 1 alpha increases expression ISO Retinaldehyde results in increased expression of PPARGC1A mRNA CTD PMID:23056435 NCBI chr14:63,095,291...63,190,688
Ensembl chr14:63,095,720...63,187,009
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 1:101,511,899...101,515,043
Ensembl chr 1:101,511,901...101,514,974
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 8:106,449,321...106,470,842
Ensembl chr 8:106,449,321...106,470,842
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 5:2,605,265...2,631,905
Ensembl chr 5:2,603,505...2,632,030
JBrowse link
G Rdh12 retinol dehydrogenase 12 increases metabolic processing ISO RDH12 protein results in increased metabolism of Retinaldehyde CTD PMID:16269441 NCBI chr 6:102,392,828...102,405,750
Ensembl chr 6:102,392,828...102,405,750
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 7:3,335,681...3,342,573
Ensembl chr 7:3,335,742...3,342,491
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 2:266,141,581...266,169,197
Ensembl chr 2:266,141,581...266,169,197
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 5:16,904,926...16,930,111
Ensembl chr 5:16,904,926...16,930,075
JBrowse link

Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19816
    role 19764
      application 19426
        solvent 16489
          formic acid 7885
            formyl group 7851
              aldehyde 7851
                retinals 39
                  retinal 39
                    11-cis-retinal + 0
                    13-cis-retinal 2
                    9-cis-retinal 9
                    all-trans-retinal + 33
Path 2
Term Annotations click to browse term
  CHEBI ontology 19816
    subatomic particle 19814
      composite particle 19814
        hadron 19814
          baryon 19814
            nucleon 19814
              atomic nucleus 19814
                atom 19814
                  main group element atom 19702
                    p-block element atom 19702
                      carbon group element atom 19608
                        carbon atom 19597
                          organic molecular entity 19597
                            organic group 18537
                              organic divalent group 18530
                                organodiyl group 18530
                                  carbonyl group 18436
                                    carbonyl compound 18436
                                      carboxylic acid 18114
                                        carboacyl group 17372
                                          univalent carboacyl group 17372
                                            formyl group 7851
                                              aldehyde 7851
                                                alpha,beta-unsaturated aldehyde 1300
                                                  enal 1300
                                                    retinal 39
                                                      11-cis-retinal + 0
                                                      13-cis-retinal 2
                                                      9-cis-retinal 9
                                                      all-trans-retinal + 33
paths to the root

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