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

General Information of Drug (ID: DR0014)
Drug Name
Nitrobenzaldehyde
Synonyms
Benzaldehyde, 4-nitro-; 4-Nitrobenzaldehyde; Benzaldehyde, p-nitro-; NX859P8MB0; p-Formylnitrobenzene; p-Nitrobenzaldehyde; p-nitro benzaldehyde; p-nitro-benzaldehyde; para-nitrobenzaldehyde; paranitrobenzaldehyde; 4-FORMYLNITROBENZENE; 4-Nitro-benzaldehyde; 4-Nitrobenzaldehydde; 4-Nitrobenzaldehyde, 99%; 4-nitro benzaldehyde; 4-nitrobenz aldehyde; 4-nitrobenzaldehyd; 4-nitrobenzaldehyde; 4-nitrobenzaldhyde; 555-16-8; AI3-52475; BXRFQSNOROATLV-UHFFFAOYSA-N; CCRIS 1675; CHEBI:66926; EINECS 209-084-5; MFCD00007346; NSC 6103; UNII-NX859P8MB0; XXH
Indication Discovery agent Investigative [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 151.12 Topological Polar Surface Area 62.9
Heavy Atom Count 11 Rotatable Bond Count 1
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
541
ChEBI ID
CHEBI:66926
CAS Number
555-16-8
Formula
C7H5NO3
Canonical SMILES
C1=CC(=CC=C1C=O)[N+](=O)[O-]
InChI
1S/C7H5NO3/c9-5-6-1-3-7(4-2-6)8(10)11/h1-5H
InChIKey
BXRFQSNOROATLV-UHFFFAOYSA-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
4-aminobenzaldehyde DM003987
11158
Reduction - Reduction 1 [5]
4-nitrobenzoate DM003983
4419940
Unclear 1 [6]
4-hydroxylaminobenzoate DM003984
11137507
Reduction - Reduction 2 [6]
Protocatechuate DM002607
72
Unclear 3 [6]
Nitrobenzaldehyde Metabolite M2 DM003986 N. A. Other reaction - Ring cleavage reaction 4 [6]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR004358 Nitrobenzaldehyde 4-nitrobenzoate Unclear Unclear [6]
MR004362 Nitrobenzaldehyde 4-aminobenzaldehyde Reduction - Reduction nfrA2 [5]
MR004359 4-nitrobenzoate 4-hydroxylaminobenzoate Reduction - Reduction Unclear [6]
MR004360 4-hydroxylaminobenzoate Protocatechuate Unclear Unclear [6]
MR004361 Protocatechuate Nitrobenzaldehyde Metabolite M2 Other reaction - Ring cleavage reaction Unclear [6]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Aldo-keto reductase 1A1 (AKR1A1) DME0098 Homo sapiens
AK1A1_HUMAN
1.1.1.2
[2]
Farnesol dehydrogenase (AKR1B15) DME0399 Homo sapiens
AK1BF_HUMAN
1.1.1.54
[3]
NADPH-dependent carbonyl reductase 3 (CBR3) DME0068 Homo sapiens
CBR3_HUMAN
1.1.1.184
[4]
Nitroreductase (NTR) DME1327 Enterococcus casseliflavus
A0A377KR04_ENTCA
1.5.1.39
[5]
Experimental Enzyme Kinetic Data of This Drug
DME Name DME Info Kinetic Data Uniprot ID REF
Aldo-keto reductase 1A1 (AKR1A1) DME0098 Km = 0.16 microM
AK1A1_HUMAN
[2]
NADPH-dependent carbonyl reductase 3 (CBR3) DME0068 Km = 0.13 microM
CBR3_HUMAN
[4]
References
1 A Publication of Reliable Methods for the Preparation of Organic Compounds.
2 The C-terminal loop of aldehyde reductase determines the substrate and inhibitor specificity. Biochemistry. 1996 Nov 12;35(45):14276-80.
3 Functional expression of novel human and murine AKR1B genes. Chem Biol Interact. 2011 May 30;191(1-3):177-84.
4 Different functions between human monomeric carbonyl reductase 3 and carbonyl reductase 1. Mol Cell Biochem. 2008 Aug;315(1-2):113-21.
5 ElNFS1, a nitroreductase gene from Enterobacter ludwigii, confers enhanced detoxification and phytoremediation of 4-nitrobenzaldehyde in rice
6 Biodegradation of 4-nitrotoluene by Pseudomonas sp. strain 4NT

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