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-OVSJKPMPSA-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+
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 |
|---|---|---|
| Occurrence of 11-cis-retinal-binding protein restricted to the retina. | 1977 Aug |
|
| Virucidal activity of retinal. | 1979 Sep |
|
| Screening for new compounds with antiherpes activity. | 1984 Oct |
|
| Determination of retinyl esters and retinol in serum or plasma by normal-phase liquid chromatography: method and applications. | 1986 Jan |
|
| The blood-brain interface. | 1990 |
|
| Antigenic cross-reactivity between human T lymphotropic virus type I (HTLV-I) and retinal antigens recognized by T cells. | 1994 Mar |
|
| Active site-directed inactivation of constitutively active mutants of rhodopsin. | 1994 Mar 4 |
|
| Structural and functional characterization of recombinant human cellular retinaldehyde-binding protein. | 1998 Mar |
|
| Metabolism of retinaldehyde and other aldehydes in soluble extracts of human liver and kidney. | 1999 Nov 19 |
|
| Effects of aldehyde dehydrogenase-2 genetic polymorphisms on metabolism of structurally different aldehydes in human liver. | 2002 Jan |
|
| 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 Apr 15 |
|
| Platelets accumulate in the diabetic retinal vasculature following endothelial death and suppress blood-retinal barrier breakdown. | 2003 Jul |
|
| Heparin-induced antiheparin-platelet antibody associated with retinal venous thrombosis. | 2003 Mar |
|
| Pathomechanisms of cystoid macular edema. | 2004 Sep-Oct |
|
| Retinal degeneration associated with RDH12 mutations results from decreased 11-cis retinal synthesis due to disruption of the visual cycle. | 2005 Dec 15 |
|
| Retinoid metabolism during development of liver cirrhosis. | 2005 Nov 15 |
|
| 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 Apr |
|
| Impacts of two point mutations of RPE65 from Leber's congenital amaurosis on the stability, subcellular localization and isomerohydrolase activity of RPE65. | 2006 Jul 24 |
|
| Kinetic properties of chimeric class I aldehyde dehydrogenases for retinal isomers. | 2006 Oct |
|
| PPARgamma controls CD1d expression by turning on retinoic acid synthesis in developing human dendritic cells. | 2006 Oct 2 |
|
| Dissection of the pathway required for generation of vitamin A and for Drosophila phototransduction. | 2007 Apr 23 |
|
| Alcohol dehydrogenase 2 is a major hepatic enzyme for human retinol metabolism. | 2007 Feb |
|
| RPE65 is essential for the function of cone photoreceptors in NRL-deficient mice. | 2007 Feb |
|
| How a small change in retinal leads to G-protein activation: initial events suggested by molecular dynamics calculations. | 2007 Feb 15 |
|
| Androgen regulation of aldehyde dehydrogenase 1A3 (ALDH1A3) in the androgen-responsive human prostate cancer cell line LNCaP. | 2007 Jun |
|
| Interactions of human serum albumin with retinoic acid, retinal and retinyl acetate. | 2007 Mar 15 |
|
| RDH10 is essential for synthesis of embryonic retinoic acid and is required for limb, craniofacial, and organ development. | 2007 May 1 |
|
| Evidence for RPE65-independent vision in the cone-dominated zebrafish retina. | 2007 Oct |
|
| Quantitative mapping of ion channel regulation by visual cycle activity in rodent photoreceptors in vivo. | 2009 Apr |
|
| Aldo-keto reductases from the AKR1B subfamily: retinoid specificity and control of cellular retinoic acid levels. | 2009 Mar 16 |
|
| Biochemical characterization of human epidermal retinol dehydrogenase 2. | 2009 Mar 16 |
|
| Human and rodent aldo-keto reductases from the AKR1B subfamily and their specificity with retinaldehyde. | 2011 May 30 |
|
| A cardiac-specific robotized cellular assay identified families of human ligands as inducers of PGC-1α expression and mitochondrial biogenesis. | 2012 |
|
| New enzymatic assay for the AKR1C enzymes. | 2013 Feb 25 |
|
| Retinoic acid biosynthesis catalyzed by retinal dehydrogenases relies on a rate-limiting conformational transition associated with substrate recognition. | 2013 Feb 25 |
|
| Aldo-keto reductases in retinoid metabolism: search for substrate specificity and inhibitor selectivity. | 2013 Feb 25 |
Patents
| Name | Type | Language | ||
|---|---|---|---|---|
|
Common Name | English | ||
|
Official Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English |
| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
|
NCI_THESAURUS |
C68299
Created by
admin on Fri Dec 15 15:14:50 GMT 2023 , Edited by admin on Fri Dec 15 15:14:50 GMT 2023
|
||
|
LOINC |
87673-0
Created by
admin on Fri Dec 15 15:14:50 GMT 2023 , Edited by admin on Fri Dec 15 15:14:50 GMT 2023
|
||
|
LOINC |
2920-7
Created by
admin on Fri Dec 15 15:14:50 GMT 2023 , Edited by admin on Fri Dec 15 15:14:50 GMT 2023
|
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
45487
Created by
admin on Fri Dec 15 15:14:50 GMT 2023 , Edited by admin on Fri Dec 15 15:14:50 GMT 2023
|
PRIMARY | |||
|
RETINAL
Created by
admin on Fri Dec 15 15:14:50 GMT 2023 , Edited by admin on Fri Dec 15 15:14:50 GMT 2023
|
PRIMARY | |||
|
626581
Created by
admin on Fri Dec 15 15:14:50 GMT 2023 , Edited by admin on Fri Dec 15 15:14:50 GMT 2023
|
PRIMARY | |||
|
m9557
Created by
admin on Fri Dec 15 15:14:50 GMT 2023 , Edited by admin on Fri Dec 15 15:14:50 GMT 2023
|
PRIMARY | Merck Index | ||
|
RR725D715M
Created by
admin on Fri Dec 15 15:14:50 GMT 2023 , Edited by admin on Fri Dec 15 15:14:50 GMT 2023
|
PRIMARY | |||
|
D012172
Created by
admin on Fri Dec 15 15:14:50 GMT 2023 , Edited by admin on Fri Dec 15 15:14:50 GMT 2023
|
PRIMARY | |||
|
2268087
Created by
admin on Fri Dec 15 15:14:50 GMT 2023 , Edited by admin on Fri Dec 15 15:14:50 GMT 2023
|
PRIMARY | |||
|
122757
Created by
admin on Fri Dec 15 15:14:50 GMT 2023 , Edited by admin on Fri Dec 15 15:14:50 GMT 2023
|
PRIMARY | |||
|
SUB182177
Created by
admin on Fri Dec 15 15:14:50 GMT 2023 , Edited by admin on Fri Dec 15 15:14:50 GMT 2023
|
PRIMARY | |||
|
204-135-8
Created by
admin on Fri Dec 15 15:14:50 GMT 2023 , Edited by admin on Fri Dec 15 15:14:50 GMT 2023
|
PRIMARY | |||
|
17898
Created by
admin on Fri Dec 15 15:14:50 GMT 2023 , Edited by admin on Fri Dec 15 15:14:50 GMT 2023
|
PRIMARY | |||
|
100000168570
Created by
admin on Fri Dec 15 15:14:50 GMT 2023 , Edited by admin on Fri Dec 15 15:14:50 GMT 2023
|
PRIMARY | |||
|
15035
Created by
admin on Fri Dec 15 15:14:50 GMT 2023 , Edited by admin on Fri Dec 15 15:14:50 GMT 2023
|
PRIMARY | |||
|
638015
Created by
admin on Fri Dec 15 15:14:50 GMT 2023 , Edited by admin on Fri Dec 15 15:14:50 GMT 2023
|
PRIMARY | |||
|
DTXSID5025998
Created by
admin on Fri Dec 15 15:14:50 GMT 2023 , Edited by admin on Fri Dec 15 15:14:50 GMT 2023
|
PRIMARY | |||
|
116-31-4
Created by
admin on Fri Dec 15 15:14:50 GMT 2023 , Edited by admin on Fri Dec 15 15:14:50 GMT 2023
|
PRIMARY | |||
|
RR725D715M
Created by
admin on Fri Dec 15 15:14:50 GMT 2023 , Edited by admin on Fri Dec 15 15:14:50 GMT 2023
|
PRIMARY | |||
|
C68300
Created by
admin on Fri Dec 15 15:14:50 GMT 2023 , Edited by admin on Fri Dec 15 15:14:50 GMT 2023
|
PRIMARY |
ACTIVE MOIETY
METABOLITE (PARENT)
