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Details

Stereochemistry ACHIRAL
Molecular Formula C20H28O
Molecular Weight 284.4357
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 4
Charge 0

SHOW SMILES / InChI
Structure of RETINAL, ALL-TRANS

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+

HIDE SMILES / InChI

Molecular Formula C20H28O
Molecular Weight 284.4357
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 4
Optical Activity NONE

Description

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

PubMed

PubMed

TitleDatePubMed
Occurrence of 11-cis-retinal-binding protein restricted to the retina.
1977 Aug
Virucidal activity of retinal.
1979 Sep
Retinal arteriolar occlusions following amniotic fluid embolism.
1984 Dec
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
Glioblastoma associated with multiple sclerosis: coincidence or induction?
1989
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
Changes of astrocytes in retinal ageing and age-related macular degeneration.
2001 Nov
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
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
Serum antibodies to retinal antigens in lung cancer and sarcoidosis.
2004
Critical role of transmembrane segment zinc binding in the structure and function of rhodopsin.
2004 Aug 20
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
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
Involvement of alcohol and aldehyde dehydrogenase activities on hepatic retinoid metabolism and its possible participation in the progression of rat liver regeneration.
2007 Feb 15
Interactions of human serum albumin with retinoic acid, retinal and retinyl acetate.
2007 Mar 15
Quantitative mapping of ion channel regulation by visual cycle activity in rodent photoreceptors in vivo.
2009 Apr
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
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
Involvement of endoplasmic reticulum stress in all-trans-retinal-induced retinal pigment epithelium degeneration.
2015 Jan
Patents
Substance Class Chemical
Created
by admin
on Tue Oct 22 05:34:20 UTC 2019
Edited
by admin
on Tue Oct 22 05:34:20 UTC 2019
Record UNII
RR725D715M
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
RETINAL, ALL-TRANS
Common Name English
RETINALDEHYD [WHO-DD]
Common Name English
RETINAL
INCI   MI  
INCI  
Official Name English
RETINAL [INCI]
Common Name English
NSC-626581
Code English
AXEROPHTHAL
Common Name English
TRANS-RETINAL
Common Name English
RETINAL TRANS-ISOMER
Common Name English
VITAMIN A ALDEHYDE
Common Name English
RETINAL [MI]
Common Name English
RETINALDEHYD
WHO-DD  
Common Name English
ALL-TRANS RETINAL
Common Name English
RETINALDEHYDE
MART.  
Common Name English
RETINALDEHYDE [MART.]
Common Name English
NSC-122757
Code English
ALL-E-RETINAL
Common Name English
ALL TRANS-RETINAL
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C68299
Created by admin on Tue Oct 22 05:34:21 UTC 2019 , Edited by admin on Tue Oct 22 05:34:21 UTC 2019
Code System Code Type Description
WIKIPEDIA
RETINAL
Created by admin on Tue Oct 22 05:34:21 UTC 2019 , Edited by admin on Tue Oct 22 05:34:21 UTC 2019
PRIMARY
MERCK INDEX
M9557
Created by admin on Tue Oct 22 05:34:21 UTC 2019 , Edited by admin on Tue Oct 22 05:34:21 UTC 2019
PRIMARY Merck Index
MESH
D012172
Created by admin on Tue Oct 22 05:34:21 UTC 2019 , Edited by admin on Tue Oct 22 05:34:21 UTC 2019
PRIMARY
EVMPD
SUB182177
Created by admin on Tue Oct 22 05:34:21 UTC 2019 , Edited by admin on Tue Oct 22 05:34:21 UTC 2019
PRIMARY
ECHA (EC/EINECS)
204-135-8
Created by admin on Tue Oct 22 05:34:21 UTC 2019 , Edited by admin on Tue Oct 22 05:34:21 UTC 2019
PRIMARY
PUBCHEM
638015
Created by admin on Tue Oct 22 05:34:21 UTC 2019 , Edited by admin on Tue Oct 22 05:34:21 UTC 2019
PRIMARY
EPA CompTox
116-31-4
Created by admin on Tue Oct 22 05:34:21 UTC 2019 , Edited by admin on Tue Oct 22 05:34:21 UTC 2019
PRIMARY
CAS
116-31-4
Created by admin on Tue Oct 22 05:34:21 UTC 2019 , Edited by admin on Tue Oct 22 05:34:21 UTC 2019
PRIMARY
NCI_THESAURUS
C68300
Created by admin on Tue Oct 22 05:34:21 UTC 2019 , Edited by admin on Tue Oct 22 05:34:21 UTC 2019
PRIMARY
Related Record Type Details
METABOLITE -> PARENT
Related Record Type Details
ACTIVE MOIETY