Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C20H28O |
| Molecular Weight | 284.4357 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 4 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(/C=C\C=C(C)\C=C\C1=C(C)CCCC1(C)C)=C\C=O
InChI
InChIKey=NCYCYZXNIZJOKI-IOUUIBBYSA-N
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+
| Molecular Formula | C20H28O |
| Molecular Weight | 284.4357 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 4 |
| Optical Activity | NONE |
Retinal, All-trans is one of the forms of vitamin A. It is an isomer of 11-cis-retinal, transductor of light into the neural signals. Retinal, All-trans is converted to retinoic acid in vivo by the action of retinal dehydrogenase. Retinal, All-trans is associated with one of the two isoforms of cellular retinol-binding proteins (CRBP-I and CRBP-II). These proteins play important roles in retinoid biology and regulation of the metabolism of retinol and retinal.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: P09455 Gene ID: 5947.0 Gene Symbol: RBP1 Target Organism: Homo sapiens (Human) |
0.06 nM [Kd] | ||
Target ID: P50120 Gene ID: 5948.0 Gene Symbol: RBP2 Target Organism: Homo sapiens (Human) |
0.13 nM [Kd] | ||
Target ID: CHEMBL3577 |
|||
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
PubMed
| Title | Date | PubMed |
|---|---|---|
| Involvement of endoplasmic reticulum stress in all-trans-retinal-induced retinal pigment epithelium degeneration. | 2015-01 |
|
| New enzymatic assay for the AKR1C enzymes. | 2013-02-25 |
|
| Retinoic acid biosynthesis catalyzed by retinal dehydrogenases relies on a rate-limiting conformational transition associated with substrate recognition. | 2013-02-25 |
|
| Aldo-keto reductases in retinoid metabolism: search for substrate specificity and inhibitor selectivity. | 2013-02-25 |
|
| Prevention of paraquat-induced apoptosis in human neuronal SH-SY5Y cells by lipocalin-type prostaglandin D synthase. | 2012-01 |
|
| A cardiac-specific robotized cellular assay identified families of human ligands as inducers of PGC-1α expression and mitochondrial biogenesis. | 2012 |
|
| Human and rodent aldo-keto reductases from the AKR1B subfamily and their specificity with retinaldehyde. | 2011-05-30 |
|
| Quantitative mapping of ion channel regulation by visual cycle activity in rodent photoreceptors in vivo. | 2009-04 |
|
| Aldo-keto reductases from the AKR1B subfamily: retinoid specificity and control of cellular retinoic acid levels. | 2009-03-16 |
|
| Biochemical characterization of human epidermal retinol dehydrogenase 2. | 2009-03-16 |
|
| Evidence for RPE65-independent vision in the cone-dominated zebrafish retina. | 2007-10 |
|
| Androgen regulation of aldehyde dehydrogenase 1A3 (ALDH1A3) in the androgen-responsive human prostate cancer cell line LNCaP. | 2007-06 |
|
| RDH10 is essential for synthesis of embryonic retinoic acid and is required for limb, craniofacial, and organ development. | 2007-05-01 |
|
| Dissection of the pathway required for generation of vitamin A and for Drosophila phototransduction. | 2007-04-23 |
|
| Interactions of human serum albumin with retinoic acid, retinal and retinyl acetate. | 2007-03-15 |
|
| Involvement of alcohol and aldehyde dehydrogenase activities on hepatic retinoid metabolism and its possible participation in the progression of rat liver regeneration. | 2007-02-15 |
|
| How a small change in retinal leads to G-protein activation: initial events suggested by molecular dynamics calculations. | 2007-02-15 |
|
| Alcohol dehydrogenase 2 is a major hepatic enzyme for human retinol metabolism. | 2007-02 |
|
| RPE65 is essential for the function of cone photoreceptors in NRL-deficient mice. | 2007-02 |
|
| Diseases caused by defects in the visual cycle: retinoids as potential therapeutic agents. | 2007 |
|
| PPARgamma controls CD1d expression by turning on retinoic acid synthesis in developing human dendritic cells. | 2006-10-02 |
|
| Kinetic properties of chimeric class I aldehyde dehydrogenases for retinal isomers. | 2006-10 |
|
| Impacts of two point mutations of RPE65 from Leber's congenital amaurosis on the stability, subcellular localization and isomerohydrolase activity of RPE65. | 2006-07-24 |
|
| Differential binding to glycotopes among the layers of three mammalian retinal neurons by man-containing N-linked glycan, T(alpha) (Galbeta1-3GalNAcalpha1-), Tn (GalNAcalpha1-Ser/Thr) and I (beta)/II (beta) (Galbeta1-3/4GlcNAcbeta-) reactive lectins. | 2006-05 |
|
| Retinoid-induced epidermal hyperplasia is mediated by epidermal growth factor receptor activation via specific induction of its ligands heparin-binding EGF and amphiregulin in human skin in vivo. | 2006-04 |
|
| Scaffold proteins and the regeneration of visual pigments. | 2006-03-24 |
|
| Small molecule RPE65 antagonists limit the visual cycle and prevent lipofuscin formation. | 2006-01-24 |
|
| Cloning of the bovine beta-carotene-15,15'-oxygenase and expression in gonadal tissues. | 2006-01 |
|
| Retinal degeneration associated with RDH12 mutations results from decreased 11-cis retinal synthesis due to disruption of the visual cycle. | 2005-12-15 |
|
| Retinoid metabolism during development of liver cirrhosis. | 2005-11-15 |
|
| Mole quantity of RPE65 and its productivity in the generation of 11-cis-retinal from retinyl esters in the living mouse eye. | 2005-07-26 |
|
| Retinal prosthesis. | 2005 |
|
| Pathomechanisms of cystoid macular edema. | 2004-12-08 |
|
| Critical role of transmembrane segment zinc binding in the structure and function of rhodopsin. | 2004-08-20 |
|
| Serum antibodies to retinal antigens in lung cancer and sarcoidosis. | 2004 |
|
| Platelets accumulate in the diabetic retinal vasculature following endothelial death and suppress blood-retinal barrier breakdown. | 2003-07 |
|
| Reduction of all-trans-retinal in the mouse liver peroxisome fraction by the short-chain dehydrogenase/reductase RRD: induction by the PPAR alpha ligand clofibrate. | 2003-04-15 |
|
| Heparin-induced antiheparin-platelet antibody associated with retinal venous thrombosis. | 2003-03 |
|
| All-trans-retinal shuts down rod cyclic nucleotide-gated ion channels: a novel role for photoreceptor retinoids in the response to bright light? | 2002-06-11 |
|
| Effects of aldehyde dehydrogenase-2 genetic polymorphisms on metabolism of structurally different aldehydes in human liver. | 2002-01 |
|
| Changes of astrocytes in retinal ageing and age-related macular degeneration. | 2001-11 |
|
| Metabolism of retinaldehyde and other aldehydes in soluble extracts of human liver and kidney. | 1999-11-19 |
|
| Structural and functional characterization of recombinant human cellular retinaldehyde-binding protein. | 1998-03 |
|
| Active site-directed inactivation of constitutively active mutants of rhodopsin. | 1994-03-04 |
|
| Antigenic cross-reactivity between human T lymphotropic virus type I (HTLV-I) and retinal antigens recognized by T cells. | 1994-03 |
|
| The blood-brain interface. | 1990 |
|
| Glioblastoma associated with multiple sclerosis: coincidence or induction? | 1989 |
|
| Retinal arteriolar occlusions following amniotic fluid embolism. | 1984-12 |
|
| Screening for new compounds with antiherpes activity. | 1984-10 |
|
| Virucidal activity of retinal. | 1979-09 |
Patents
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 22:06:09 GMT 2025
by
admin
on
Mon Mar 31 22:06:09 GMT 2025
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| Record UNII |
91058V6HCH
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| Record Status |
Validated (UNII)
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| Record Version |
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BINDER->LIGAND |
