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 |
|---|---|---|
| Retinal arteriolar occlusions following amniotic fluid embolism. | 1984 Dec |
|
| Determination of retinyl esters and retinol in serum or plasma by normal-phase liquid chromatography: method and applications. | 1986 Jan |
|
| Glioblastoma associated with multiple sclerosis: coincidence or induction? | 1989 |
|
| The blood-brain interface. | 1990 |
|
| Structural and functional characterization of recombinant human cellular retinaldehyde-binding protein. | 1998 Mar |
|
| Effects of aldehyde dehydrogenase-2 genetic polymorphisms on metabolism of structurally different aldehydes in human liver. | 2002 Jan |
|
| All-trans-retinal shuts down rod cyclic nucleotide-gated ion channels: a novel role for photoreceptor retinoids in the response to bright light? | 2002 Jun 11 |
|
| Serum antibodies to retinal antigens in lung cancer and sarcoidosis. | 2004 |
|
| Pathomechanisms of cystoid macular edema. | 2004 Sep-Oct |
|
| Retinal prosthesis. | 2005 |
|
| Mole quantity of RPE65 and its productivity in the generation of 11-cis-retinal from retinyl esters in the living mouse eye. | 2005 Jul 26 |
|
| Cloning of the bovine beta-carotene-15,15'-oxygenase and expression in gonadal tissues. | 2006 Jan |
|
| Small molecule RPE65 antagonists limit the visual cycle and prevent lipofuscin formation. | 2006 Jan 24 |
|
| 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 |
|
| 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 May |
|
| Scaffold proteins and the regeneration of visual pigments. | 2006 Nov-Dec |
|
| 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 |
|
| RPE65 is essential for the function of cone photoreceptors in NRL-deficient mice. | 2007 Feb |
|
| Androgen regulation of aldehyde dehydrogenase 1A3 (ALDH1A3) in the androgen-responsive human prostate cancer cell line LNCaP. | 2007 Jun |
|
| RDH10 is essential for synthesis of embryonic retinoic acid and is required for limb, craniofacial, and organ development. | 2007 May 1 |
|
| Biochemical characterization of human epidermal retinol dehydrogenase 2. | 2009 Mar 16 |
|
| Prevention of paraquat-induced apoptosis in human neuronal SH-SY5Y cells by lipocalin-type prostaglandin D synthase. | 2012 Jan |
|
| 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 |
Patents
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 08:28:30 UTC 2023
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admin
on
Sat Dec 16 08:28:30 UTC 2023
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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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m9557
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16066
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DTXSID80415057
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BINDER->LIGAND |
