U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C20H28O
Molecular Weight 284.4365
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 4
Charge 0

SHOW SMILES / InChI
Structure of RETINAL, ALL-TRANS

SMILES

C/C(=C(/[H])\C(\[H])=C(/[H])\C(=C(/[H])\C=O)\C)/C(/[H])=C(\[H])/C1=C(C)CCCC1(C)C

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 284.4365
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

Sources: DOI: 10.1038/134065a0

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
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]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Screening for new compounds with antiherpes activity.
1984 Oct
The blood-brain interface.
1990
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
Changes of astrocytes in retinal ageing and age-related macular degeneration.
2001 Nov
Small molecule RPE65 antagonists limit the visual cycle and prevent lipofuscin formation.
2006 Jan 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
Diseases caused by defects in the visual cycle: retinoids as potential therapeutic agents.
2007
How a small change in retinal leads to G-protein activation: initial events suggested by molecular dynamics calculations.
2007 Feb 15
RDH10 is essential for synthesis of embryonic retinoic acid and is required for limb, craniofacial, and organ development.
2007 May 1
Human and rodent aldo-keto reductases from the AKR1B subfamily and their specificity with retinaldehyde.
2011 May 30
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Sat Jun 26 07:34:24 UTC 2021
Edited
by admin
on Sat Jun 26 07:34:24 UTC 2021
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 Sat Jun 26 07:34:24 UTC 2021 , Edited by admin on Sat Jun 26 07:34:24 UTC 2021
LOINC 87673-0
Created by admin on Sat Jun 26 07:34:24 UTC 2021 , Edited by admin on Sat Jun 26 07:34:24 UTC 2021
LOINC 2920-7
Created by admin on Sat Jun 26 07:34:24 UTC 2021 , Edited by admin on Sat Jun 26 07:34:24 UTC 2021
Code System Code Type Description
WIKIPEDIA
RETINAL
Created by admin on Sat Jun 26 07:34:24 UTC 2021 , Edited by admin on Sat Jun 26 07:34:24 UTC 2021
PRIMARY
MERCK INDEX
M9557
Created by admin on Sat Jun 26 07:34:24 UTC 2021 , Edited by admin on Sat Jun 26 07:34:24 UTC 2021
PRIMARY Merck Index
MESH
D012172
Created by admin on Sat Jun 26 07:34:24 UTC 2021 , Edited by admin on Sat Jun 26 07:34:24 UTC 2021
PRIMARY
RXCUI
2268087
Created by admin on Sat Jun 26 07:34:24 UTC 2021 , Edited by admin on Sat Jun 26 07:34:24 UTC 2021
PRIMARY
EVMPD
SUB182177
Created by admin on Sat Jun 26 07:34:24 UTC 2021 , Edited by admin on Sat Jun 26 07:34:24 UTC 2021
PRIMARY
ECHA (EC/EINECS)
204-135-8
Created by admin on Sat Jun 26 07:34:24 UTC 2021 , Edited by admin on Sat Jun 26 07:34:24 UTC 2021
PRIMARY
PUBCHEM
638015
Created by admin on Sat Jun 26 07:34:24 UTC 2021 , Edited by admin on Sat Jun 26 07:34:24 UTC 2021
PRIMARY
EPA CompTox
116-31-4
Created by admin on Sat Jun 26 07:34:24 UTC 2021 , Edited by admin on Sat Jun 26 07:34:24 UTC 2021
PRIMARY
CAS
116-31-4
Created by admin on Sat Jun 26 07:34:24 UTC 2021 , Edited by admin on Sat Jun 26 07:34:24 UTC 2021
PRIMARY
FDA UNII
RR725D715M
Created by admin on Sat Jun 26 07:34:24 UTC 2021 , Edited by admin on Sat Jun 26 07:34:24 UTC 2021
PRIMARY
NCI_THESAURUS
C68300
Created by admin on Sat Jun 26 07:34:24 UTC 2021 , Edited by admin on Sat Jun 26 07:34:24 UTC 2021
PRIMARY
Related Record Type Details
METABOLITE -> PARENT
Related Record Type Details
ACTIVE MOIETY