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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
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 No
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

Wald, G.
3
Sources: DOI: 10.1038/134065a0

Approval Year

2019
334
Targets

Targets

Primary TargetPharmacologyConditionPotency
Retinol-binding protein 1
3
Target ID: P09455
Gene ID: 5947.0
Gene Symbol: RBP1
Target Organism: Homo sapiens (Human)
Binding Agent
1064
 0.06 nM [Kd]
Retinol-binding protein 2
3
Target ID: P50120
Gene ID: 5948.0
Gene Symbol: RBP2
Target Organism: Homo sapiens (Human)
Binding Agent
1064
 0.13 nM [Kd]
Substrate
661
Substrate
661
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Retinal arteriolar occlusions following amniotic fluid embolism.
1984 Dec
Platelets accumulate in the diabetic retinal vasculature following endothelial death and suppress blood-retinal barrier breakdown.
2003 Jul
Critical role of transmembrane segment zinc binding in the structure and function of rhodopsin.
2004 Aug 20
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
Kinetic properties of chimeric class I aldehyde dehydrogenases for retinal isomers.
2006 Oct
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
Evidence for RPE65-independent vision in the cone-dominated zebrafish retina.
2007 Oct
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
Involvement of endoplasmic reticulum stress in all-trans-retinal-induced retinal pigment epithelium degeneration.
2015 Jan
Patents

Patents

04543417
3
07323589
3
US 3060229
3

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:14:50 UTC 2023
Edited
by admin
on Fri Dec 15 15:14:50 UTC 2023
Record UNII
RR725D715M
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
RETINAL, ALL-TRANS
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
Retinaldehyd [WHO-DD]
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 Fri Dec 15 15:14:50 UTC 2023 , Edited by admin on Fri Dec 15 15:14:50 UTC 2023
LOINC 87673-0
Created by admin on Fri Dec 15 15:14:50 UTC 2023 , Edited by admin on Fri Dec 15 15:14:50 UTC 2023
LOINC 2920-7
Created by admin on Fri Dec 15 15:14:50 UTC 2023 , Edited by admin on Fri Dec 15 15:14:50 UTC 2023
Code System Code Type Description
CHEBI
45487
Created by admin on Fri Dec 15 15:14:50 UTC 2023 , Edited by admin on Fri Dec 15 15:14:50 UTC 2023
PRIMARY
WIKIPEDIA
RETINAL
Created by admin on Fri Dec 15 15:14:50 UTC 2023 , Edited by admin on Fri Dec 15 15:14:50 UTC 2023
PRIMARY
NSC
626581
Created by admin on Fri Dec 15 15:14:50 UTC 2023 , Edited by admin on Fri Dec 15 15:14:50 UTC 2023
PRIMARY
MERCK INDEX
m9557
Created by admin on Fri Dec 15 15:14:50 UTC 2023 , Edited by admin on Fri Dec 15 15:14:50 UTC 2023
PRIMARY Merck Index
DAILYMED
RR725D715M
Created by admin on Fri Dec 15 15:14:50 UTC 2023 , Edited by admin on Fri Dec 15 15:14:50 UTC 2023
PRIMARY
MESH
D012172
Created by admin on Fri Dec 15 15:14:50 UTC 2023 , Edited by admin on Fri Dec 15 15:14:50 UTC 2023
PRIMARY
RXCUI
2268087
Created by admin on Fri Dec 15 15:14:50 UTC 2023 , Edited by admin on Fri Dec 15 15:14:50 UTC 2023
PRIMARY
NSC
122757
Created by admin on Fri Dec 15 15:14:50 UTC 2023 , Edited by admin on Fri Dec 15 15:14:50 UTC 2023
PRIMARY
EVMPD
SUB182177
Created by admin on Fri Dec 15 15:14:50 UTC 2023 , Edited by admin on Fri Dec 15 15:14:50 UTC 2023
PRIMARY
ECHA (EC/EINECS)
204-135-8
Created by admin on Fri Dec 15 15:14:50 UTC 2023 , Edited by admin on Fri Dec 15 15:14:50 UTC 2023
PRIMARY
CHEBI
17898
Created by admin on Fri Dec 15 15:14:50 UTC 2023 , Edited by admin on Fri Dec 15 15:14:50 UTC 2023
PRIMARY
SMS_ID
100000168570
Created by admin on Fri Dec 15 15:14:50 UTC 2023 , Edited by admin on Fri Dec 15 15:14:50 UTC 2023
PRIMARY
CHEBI
15035
Created by admin on Fri Dec 15 15:14:50 UTC 2023 , Edited by admin on Fri Dec 15 15:14:50 UTC 2023
PRIMARY
PUBCHEM
638015
Created by admin on Fri Dec 15 15:14:50 UTC 2023 , Edited by admin on Fri Dec 15 15:14:50 UTC 2023
PRIMARY
EPA CompTox
DTXSID5025998
Created by admin on Fri Dec 15 15:14:50 UTC 2023 , Edited by admin on Fri Dec 15 15:14:50 UTC 2023
PRIMARY
CAS
116-31-4
Created by admin on Fri Dec 15 15:14:50 UTC 2023 , Edited by admin on Fri Dec 15 15:14:50 UTC 2023
PRIMARY
FDA UNII
RR725D715M
Created by admin on Fri Dec 15 15:14:50 UTC 2023 , Edited by admin on Fri Dec 15 15:14:50 UTC 2023
PRIMARY
NCI_THESAURUS
C68300
Created by admin on Fri Dec 15 15:14:50 UTC 2023 , Edited by admin on Fri Dec 15 15:14:50 UTC 2023
PRIMARY
Related Record Type Details
Structure of TRETINOIN
METABOLITE -> PARENT
Related Record Type Details
Structure of RETINAL, ALL-TRANS
ACTIVE MOIETY
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