Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR2032)
Drug Name
All-trans-retinal
Synonyms
E-Retinal; RR725D715M; Retinal, all-trans-; Retinaldehyde (VAN); Retinene 1; Retinyl aldehyde; TOCOPHEROL, ALPHA; Vitamin A1 aldehyde; all-E-Retinal; all-trans-Retinal; all-trans-Retinaldehyde; all-trans-Retinene; all-trans-Vitamin A aldehyde; axerophthal; retinal; retinaldehyde; retinene; trans-Retinal; trans-Vitamin A aldehyde; vitamin A aldehyde; .alpha.-Retinene; 116-31-4; BRN 1914183; CHEBI:17898; EINECS 204-135-8; MFCD00001550; NCYCYZXNIZJOKI-OVSJKPMPSA-N; NSC 122757; NSC 626581; NSC626581; UNII-RR725D715M
Indication Discovery agent Investigative [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 284.4 Topological Polar Surface Area 17.1
Heavy Atom Count 21 Rotatable Bond Count 5
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 1
Cross-matching ID
PubChem CID
638015
PubChem SID
3136 ; 3666 ; 83356 ; 228445 ; 416401 ; 416402 ; 493006 ; 589152 ; 3157260 ; 8143959 ; 8704598 ; 10504630 ; 10524847 ; 12276012 ; 14775466 ; 17388687 ; 24702066 ; 24899355 ; 24899382 ; 43760279 ; 48424039 ; 48425697 ; 49854777 ; 53790090 ; 53812631 ; 57407725 ; 77047160 ; 91615887 ; 103282386 ; 103847254 ; 113528124 ; 113584862 ; 117624017 ; 117682346 ; 124890043 ; 124890044 ; 124890045 ; 124890046 ; 124890047 ; 126523991 ; 126637303 ; 134975373 ; 135651434 ; 137004766 ; 137005733 ; 142478968 ; 144208203 ; 162219414 ; 164806111 ; 175265990
ChEBI ID
CHEBI:17898
CAS Number
116-31-4
TTD Drug ID
D05SOU
Formula
C20H28O
Canonical SMILES
CC1=C(C(CCC1)(C)C)C=CC(=CC=CC(=CC=O)C)C
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
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
Retinol DM001733
445354
Unclear 1 [3] , [4]
Retinyl esters DM001734
25058155
Unclear 2 [3] , [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000143 All-trans-retinal Retinol Unclear Unclear [3], [4]
MR000142 Retinol Retinyl esters Unclear Dhrs3 [3], [4]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Aldehyde dehydrogenase 1 (ALDH1) DME0286 Homo sapiens
AL1A1_HUMAN
1.2.1.36
[2]
Short-chain dehydrogenase/reductase retSDR1 (DHRS3) DME0414 Homo sapiens
DHRS3_HUMAN
1.1.1.300
[3]
Experimental Enzyme Kinetic Data of This Drug
DME Name DME Info Kinetic Data Uniprot ID REF
Aldehyde dehydrogenase 1 (ALDH1) DME0286 Km = 0.0081 microM
AL1A1_HUMAN
[2]
References
1 The IUPHAR/BPS Guide to PHARMACOLOGY in 2020: extending immunopharmacology content and introducing the IUPHAR/MMV Guide to MALARIA PHARMACOLOGY. Nucleic Acids Res. 2020 Jan 8;48(D1):D1006-D1021. (Ligand id: 2350).
2 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.
3 Metabolism of retinaldehyde isomers in pregnant rats: 13-cis- and all-trans-retinaldehyde, but not 9-cis-retinaldehyde, yield very similar patterns of retinoid metabolites Drug Metab Dispos. 1999 Mar;27(3):317-21.
4 PNPLA2 mobilizes retinyl esters from retinosomes and promotes the generation of 11-cis-retinal in the visual cycle. Cell Rep. 2023 Feb 8;42(2):112091. doi: 10.1016/j.celrep.2023.112091.

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