4-Nitrocatechol (BioCAD00000004484)

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Metabolite Card

Formula: C6H5NO4 (155.0219)
SMILES: OC1=C(O)C=C(C=C1)[N+]([O-])=O

Synonyms [en]

4-nitrocatechol; 4-nitrobenzene-1,2-diol; 4-NITROPYROCATECHOL; 4-Nitrobenzcatechin; 1,2-Dihydroxy-4-nitrobenzene; p-Nitrocatechol

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

4-Nitrocatechol. 数据之源，洞见之始. SMRUCC genomics institute, a synthetic life researcher from China. https://biocad_registry.innovation.ac.cn/s/(-)-arctiin (retrieved 2026-01-03) (CAD Registry RN: BioCAD00000004484). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

4-Nitrocatechol is the by-product of the hydroxylation of 4-nitrophenol by the human cytochrome P450 (CYP) 2E1. This reaction is a useful metabolic marker for the presence of functional cytochrome P450 2E1 in mammalian cell microsomes. Hepatic and extrahepatic microsomal cytochrome P450 isozymes further catalyze the reduction of p-nitrocatechol into p-aminophenol (PMID: 8267647, 8214571, 8267647).

Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 3316-09-4
  • PubChem: 3505109
  • ChEBI: ChEBI:16318
  • HMDB: HMDB0002916
  • HMDB: HMDB02916
  • KEGG: C02235
  • BioCyc: CPD-158
  • NCBI MeSH: 4-nitrocatechol
  • DrugBank: DB03407
  • RefMet: RM0041308
  • MoNA: FiehnHILIC001002
  • MoNA: FiehnHILIC002538
  • MoNA: FiehnLib000867
  • MoNA: HMDB0002916_c_ms_102556
  • MoNA: HMDB0002916_c_ms_102557
  • MoNA: HMDB0002916_c_ms_99785
  • MoNA: HMDB0062694_c_ms_102556
  • MoNA: HMDB0062694_c_ms_102557
  • MoNA: HMDB0062694_c_ms_99785
  • Metlin: METLIN_58136
  • Coconut NaturalProduct: CNP0487366.0
  • Coconut NaturalProduct: CNP0593657.0

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R03023 1.14.13.29 4-nitrophenol,NADH:oxygen oxidoreductase (2-hydroxylating)
KEGG:R05265 1.14.-.- C02235 + C00007 + 3 C00080<=>C02814 + C00088 + C00001
BioCyc:4-NITROPHENOL-2-MONOOXYGENASE-RXN 1.14.13.29 P-NITROPHENOL + NADH + OXYGEN-MOLECULE + 2 PROTON --> CPD-158 + NAD + WATER
BioCyc:RXN-14162 1.14.13.29 P-NITROPHENOL + NADPH + OXYGEN-MOLECULE + 2 PROTON --> CPD-158 + NADP + WATER
BioCyc:RXN-11965 1.14.13.166 CPD-158 + OXYGEN-MOLECULE + NADH-P-OR-NOP --> HYDROXYBENZOQUINONE + NITRITE + WATER + NAD-P-OR-NOP + PROTON
BioCyc:RXN-16800 1.14.12.23 13-DINITROBENZENE + OXYGEN-MOLECULE + NADH --> CPD-158 + NITRITE + NAD
BioCyc:RXN-20165 3.1.6.1 CPD-21754 + WATER --> CPD-158 + SULFATE + PROTON
BioCyc:RXN-16801 1.14.12.23 CPD-18112 + OXYGEN-MOLECULE + NADH --> CPD-158 + NITRITE + NAD
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Organism Source

Taxonomy Source

  1. Homo sapiens [ncbi taxid: 9606]

Pathway Synthetic

pathway id name
BioCyc:META_PWY-5488 4-nitrophenol degradation II
View All Pathways