Details of the Drug

General Information of Drug (ID: DM6CEVB)

Drug Name
all-trans-retinal
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Drug Type
Small molecular drug
Structure
3D MOL is unavailable 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 284.4
Logarithm of the Partition Coefficient (xlogp) 6.2
Rotatable Bond Count (rotbonds) 5
Hydrogen Bond Donor Count (hbonddonor) 0
Hydrogen Bond Acceptor Count (hbondacc) 1
Chemical Identifiers
Formula
C20H28O
IUPAC Name
(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenal
Canonical SMILES
CC1=C(C(CCC1)(C)C)/C=C/C(=C/C=C/C(=C/C=O)/C)/C
InChI
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+
InChIKey
NCYCYZXNIZJOKI-OVSJKPMPSA-N
Cross-matching ID
PubChem CID
638015
ChEBI ID
CHEMBL81379
CAS Number
116-31-4
TTD ID
D05SOU
INTEDE ID
DR2032
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Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Cyclic nucleotide-gated channel alpha-2 (CNGA2) TT8SJGB CNGA2_HUMAN Inhibitor (gating inhibitor) [2]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Aldehyde dehydrogenase 1 (ALDH1)
Main DME 		DE2JP1Y AL1A1_HUMAN Substrate [3]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Albumin (ALB) OTVMM513 ALBU_HUMAN Protein Interaction/Cellular Processes [4]
Aldehyde dehydrogenase, mitochondrial (ALDH2) OTKJ9I3N ALDH2_HUMAN Regulation of Drug Effects [5]
Aldo-keto reductase family 1 member B1 (AKR1B1) OTRX72TH ALDR_HUMAN Biotransformations [6]
Aldo-keto reductase family 1 member B10 (AKR1B10) OTOA4HTH AK1BA_HUMAN Regulation of Drug Effects [7]
Aldo-keto reductase family 1 member C3 (AKR1C3) OTU2SXBA AK1C3_HUMAN Biotransformations [8]
All-trans-retinol dehydrogenase ADH1B (ADH1B) OTV3TB81 ADH1B_HUMAN Regulation of Drug Effects [9]
Cyclic AMP-dependent transcription factor ATF-4 (ATF4) OTRFV19J ATF4_HUMAN Gene/Protein Processing [10]
DNA damage-inducible transcript 3 protein (DDIT3) OTI8YKKE DDIT3_HUMAN Gene/Protein Processing [10]
Epidermal retinol dehydrogenase 2 (SDR16C5) OT7BJD1M RDHE2_HUMAN Biotransformations [11]
Peroxisome proliferator-activated receptor gamma coactivator 1-alpha (PPARGC1A) OTHCDQ22 PRGC1_HUMAN Gene/Protein Processing [12]
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References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 2350).
2 All-trans-retinal shuts down rod cyclic nucleotide-gated ion channels: a novel role for photoreceptor retinoids in the response to bright light Proc Natl Acad Sci U S A. 2002 Jun 11;99(12):8372-7.
3 Retinoic acid biosynthesis catalyzed by retinal dehydrogenases relies on a rate-limiting conformational transition associated with substrate recognition. Chem Biol Interact. 2013 Feb 25;202(1-3):78-84.
4 Interactions of human serum albumin with retinoic acid, retinal and retinyl acetate. Biochem Pharmacol. 2007 Mar 15;73(6):901-10. doi: 10.1016/j.bcp.2006.11.023. Epub 2006 Dec 2.
5 Effects of aldehyde dehydrogenase-2 genetic polymorphisms on metabolism of structurally different aldehydes in human liver. Drug Metab Dispos. 2002 Jan;30(1):69-73. doi: 10.1124/dmd.30.1.69.
6 Aldo-keto reductases from the AKR1B subfamily: retinoid specificity and control of cellular retinoic acid levels. Chem Biol Interact. 2009 Mar 16;178(1-3):171-7. doi: 10.1016/j.cbi.2008.10.027. Epub 2008 Oct 25.
7 Human and rodent aldo-keto reductases from the AKR1B subfamily and their specificity with retinaldehyde. Chem Biol Interact. 2011 May 30;191(1-3):199-205. doi: 10.1016/j.cbi.2011.02.007. Epub 2011 Feb 15.
8 New enzymatic assay for the AKR1C enzymes. Chem Biol Interact. 2013 Feb 25;202(1-3):204-9.
9 Alcohol dehydrogenase 2 is a major hepatic enzyme for human retinol metabolism. Cell Mol Life Sci. 2007 Feb;64(4):498-505. doi: 10.1007/s00018-007-6449-8.
10 Involvement of endoplasmic reticulum stress in all-trans-retinal-induced retinal pigment epithelium degeneration. Toxicol Sci. 2015 Jan;143(1):196-208. doi: 10.1093/toxsci/kfu223. Epub 2014 Oct 20.
11 Characterization of human short chain dehydrogenase/reductase SDR16C family members related to retinol dehydrogenase 10. Chem Biol Interact. 2017 Oct 1;276:88-94. doi: 10.1016/j.cbi.2016.10.019. Epub 2016 Oct 25.
12 A cardiac-specific robotized cellular assay identified families of human ligands as inducers of PGC-1 expression and mitochondrial biogenesis. PLoS One. 2012;7(10):e46753. doi: 10.1371/journal.pone.0046753. Epub 2012 Oct 3.