4-Hydroxylamino-2,6-dinitrotoluene (BioCAD00000004391)

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Metabolite Card

Formula: C7H7N3O5 (213.0386)
SMILES: CC1=C(C=C(NO)C=C1[N+]([O-])=O)[N+]([O-])=O

Synonyms [en]

4-hydroxylamino-2,6-dinitrotoluene; 4-Hadnt; N-(4-Methyl-3,5-dinitrophenyl)hydroxylamine; Benzenamine; 5-dinitro-; 4-hydroxyamino-2

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

4-Hydroxylamino-2,6-dinitrotoluene. 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: BioCAD00000004391). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

4-hydroxylamino-2,6-dinitrotoluene, also known as 4-hadnt, is a member of the class of compounds known as dinitrotoluenes. Dinitrotoluenes are organic aromatic compounds containing a benzene that carries a single methyl group and exactly two nitro groups. 4-hydroxylamino-2,6-dinitrotoluene is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 4-hydroxylamino-2,6-dinitrotoluene can be found in a number of food items such as elderberry, pigeon pea, tea leaf willow, and tree fern, which makes 4-hydroxylamino-2,6-dinitrotoluene a potential biomarker for the consumption of these food products.

Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 59283-75-9
  • PubChem: 5375469
  • ChEBI: ChEBI:20408
  • HMDB: HMDB0304181
  • KEGG: C16392
  • BioCyc: CPD-10457
  • NCBI MeSH: 4-hydroxylamino-2,6-dinitrotoluene
  • Metlin: METLIN_71180
  • Coconut NaturalProduct: CNP0583565.0

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R08014 1.-.-.- C16391 + 2 C00005 + 2 C00080<=>C16392 + 2 C00006 + C00001
KEGG:R08015 1.7.1.- C16392 + 2 C00005 + 2 C00080<=>C16402 + 2 C00006 + C00001
KEGG:R08017 1.-.-.- C16391 + 2 C00004 + 2 C00080<=>C16392 + 2 C00003 + C00001
KEGG:R08018 1.7.1.- C16392 + C00004 + C00080<=>C16394 + C00003 + C00001
KEGG:R08019 1.7.1.- C16392 + C00005 + C00080<=>C16394 + C00006 + C00001
KEGG:R08020 4 C16392 + C00007<=>2 C16413 + 4 C00001
KEGG:R08037 2 C16392 + 2 C16393 + C00007<=>2 C16412 + 4 C00001
Rhea:RHEA:80096 2,4,6-trinitrotoluene + 2 NADH + 2 H+ => 4-hydroxylamino-2,6-dinitrotoluene + 2 NAD+ + H2O
Rhea:RHEA:80097 4-hydroxylamino-2,6-dinitrotoluene + 2 NAD+ + H2O => 2,4,6-trinitrotoluene + 2 NADH + 2 H+
Rhea:RHEA:80098 2,4,6-trinitrotoluene + 2 NADH + 2 H+ <=> 4-hydroxylamino-2,6-dinitrotoluene + 2 NAD+ + H2O
Rhea:RHEA:80104 2,4,6-trinitrotoluene + 2 NADPH + 2 H+ => 4-hydroxylamino-2,6-dinitrotoluene + 2 NADP+ + H2O
Rhea:RHEA:80105 4-hydroxylamino-2,6-dinitrotoluene + 2 NADP+ + H2O => 2,4,6-trinitrotoluene + 2 NADPH + 2 H+
Rhea:RHEA:80106 2,4,6-trinitrotoluene + 2 NADPH + 2 H+ <=> 4-hydroxylamino-2,6-dinitrotoluene + 2 NADP+ + H2O
Rhea:RHEA:80112 4-hydroxylamino-2,6-dinitrotoluene + NADPH + H+ => 4-amino-2,6-dinitrotoluene + NADP+ + H2O
Rhea:RHEA:80113 4-amino-2,6-dinitrotoluene + NADP+ + H2O => 4-hydroxylamino-2,6-dinitrotoluene + NADPH + H+
Rhea:RHEA:80114 4-hydroxylamino-2,6-dinitrotoluene + NADPH + H+ <=> 4-amino-2,6-dinitrotoluene + NADP+ + H2O
Rhea:RHEA:80116 4-hydroxylamino-2,6-dinitrotoluene + 2 NADPH + 2 H+ => 2,4-dihydroxylamino-6-nitrotoluene + 2 NADP+ + H2O
Rhea:RHEA:80117 2,4-dihydroxylamino-6-nitrotoluene + 2 NADP+ + H2O => 4-hydroxylamino-2,6-dinitrotoluene + 2 NADPH + 2 H+
Rhea:RHEA:80118 4-hydroxylamino-2,6-dinitrotoluene + 2 NADPH + 2 H+ <=> 2,4-dihydroxylamino-6-nitrotoluene + 2 NADP+ + H2O
Rhea:RHEA:80480 4-hydroxylamino-2,6-dinitrotoluene + UDP-α-D-glucose => 4-hydroxylamino-2,6-dinitrotoluene-O-β-D-glucoside + UDP + H+
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Organism Source

Taxonomy Source

Pathway Synthetic

pathway id name
BioCyc:ARA_PWY-6051 2,4,6-trinitrotoluene degradation
BioCyc:META_PWY-6051 2,4,6-trinitrotoluene degradation
PlantCyc:SPIRODELA_PWY-6051 2,4,6-trinitrotoluene degradation
PlantCyc:AHYPOCHONDRIACUS_PWY-6051 2,4,6-trinitrotoluene degradation
PlantCyc:BOLERACEA_OLERACEA_PWY-6051 2,4,6-trinitrotoluene degradation
PlantCyc:BREADWHEAT_PWY-6051 2,4,6-trinitrotoluene degradation
PlantCyc:CANNUUM_PWY-6051 2,4,6-trinitrotoluene degradation
PlantCyc:CARIETINUM_ICC4958_PWY-6051 2,4,6-trinitrotoluene degradation
PlantCyc:CRUBELLA_PWY-6051 2,4,6-trinitrotoluene degradation
PlantCyc:GRAIMONDII_PWY-6051 2,4,6-trinitrotoluene degradation
PlantCyc:KFEDTSCHENKOI_PWY-6051 2,4,6-trinitrotoluene degradation
PlantCyc:MGUTTATUS_PWY-6051 2,4,6-trinitrotoluene degradation
PlantCyc:LER_PWY-6051 2,4,6-trinitrotoluene degradation
PlantCyc:OGLABERRIMA_PWY-6051 2,4,6-trinitrotoluene degradation
PlantCyc:ORUFIPOGON_PWY-6051 2,4,6-trinitrotoluene degradation
PlantCyc:PHALLII_PWY-6051 2,4,6-trinitrotoluene degradation
PlantCyc:PLANT_PWY-6051 2,4,6-trinitrotoluene degradation
PlantCyc:RCHINENSIS_PWY-6051 2,4,6-trinitrotoluene degradation
PlantCyc:REDCLOVER_PWY-6051 2,4,6-trinitrotoluene degradation
PlantCyc:RMULTIFLORA_PWY-6051 2,4,6-trinitrotoluene degradation
View All Pathways