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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-06-18 17:47:59 UTC

Update Date

2023-02-21 17:30:08 UTC

HMDB ID

HMDB0060659

Secondary Accession Numbers

HMDB60659

Metabolite Identification

Common Name

1-Methyl-4-nitroimidazole

Description

1-Methyl-4-nitroimidazole is a metabolite of azathioprine. Azathioprine is a purine analogue immunosuppressive drug. It is used to prevent rejection following organ transplantation, and to treat a vast array of autoimmune diseases, including rheumatoid arthritis, pemphigus, inflammatory bowel disease, multiple sclerosis, autoimmune hepatitis, atopic dermatitis, myasthenia gravis, neuromyelitis optica or Devic's disease, restrictive lung disease, and others. (Wikipedia)

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₄H₅N₃O₂

Average Molecular Weight

127.1014

Monoisotopic Molecular Weight

127.038176419

IUPAC Name

1-methyl-4-nitro-1H-imidazole

Traditional Name

1-methyl-4-nitroimidazole

CAS Registry Number

Not Available

SMILES

CN1C=NC(=C1)[N+]([O-])=O

InChI Identifier

InChI=1S/C4H5N3O2/c1-6-2-4(5-3-6)7(8)9/h2-3H,1H3

InChI Key

HSCOLDQJZRZQMV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as nitroimidazoles. Nitroimidazoles are compounds containing an imidazole ring which bears a nitro group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azoles

Sub Class

Imidazoles

Direct Parent

Nitroimidazoles

Alternative Parents

Substituents

Nitroaromatic compound
Nitroimidazole
N-substituted imidazole
Imidolactam
Heteroaromatic compound
C-nitro compound
Organic nitro compound
Organic oxoazanium
Allyl-type 1,3-dipolar organic compound
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Azacycle
Organic nitrogen compound
Organonitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

C-nitro compound (CHEBI:80615 )
imidazoles (CHEBI:80615 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060659)

Organ

Liver (HMDB: HMDB0060659)
Kidney (HMDB: HMDB0060659)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060659)

Source

Endogenous

Endogenous (HMDB: HMDB0060659)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Azathioprine Action Pathway (PathBank: SMP0000427)

Metabolic pathway

Azathioprine Metabolism Pathway (PathBank: SMP0000645)

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	3.14 g/L	ALOGPS
logP	-0.23	ALOGPS
logP	0.61	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Basic)	-0.34	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	63.64 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	31.55 m³·mol⁻¹	ChemAxon
Polarizability	11.09 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	125.857	31661259
DarkChem	[M-H]-	122.884	31661259
DeepCCS	[M+H]+	124.11	30932474
DeepCCS	[M-H]-	121.129	30932474
DeepCCS	[M-2H]-	158.336	30932474
DeepCCS	[M+Na]+	132.809	30932474
AllCCS	[M+H]+	127.4	32859911
AllCCS	[M+H-H2O]+	122.8	32859911
AllCCS	[M+NH4]+	131.8	32859911
AllCCS	[M+Na]+	133.0	32859911
AllCCS	[M-H]-	121.4	32859911
AllCCS	[M+Na-2H]-	123.5	32859911
AllCCS	[M+HCOO]-	125.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1-Methyl-4-nitroimidazole	CN1C=NC(=C1)[N+]([O-])=O	1875.5	Standard polar	33892256
1-Methyl-4-nitroimidazole	CN1C=NC(=C1)[N+]([O-])=O	1162.6	Standard non polar	33892256
1-Methyl-4-nitroimidazole	CN1C=NC(=C1)[N+]([O-])=O	1476.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 1-Methyl-4-nitroimidazole GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-9500000000-5572508a2c2c51823d13	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-Methyl-4-nitroimidazole GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Methyl-4-nitroimidazole 10V, Positive-QTOF	splash10-004i-1900000000-d877350c3caef4c84344	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Methyl-4-nitroimidazole 20V, Positive-QTOF	splash10-0il0-4900000000-c8ce22a6a8141005a467	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Methyl-4-nitroimidazole 40V, Positive-QTOF	splash10-0a59-9100000000-40b7719a2cb99667331d	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Methyl-4-nitroimidazole 10V, Negative-QTOF	splash10-004i-0900000000-bf396a90d19c67b3089a	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Methyl-4-nitroimidazole 20V, Negative-QTOF	splash10-0002-9000000000-088fbb049b50fa302286	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Methyl-4-nitroimidazole 40V, Negative-QTOF	splash10-0ul1-9000000000-6cc95eb36814b01901d4	2017-10-06	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Name	SMPDB/PathBank	KEGG
Azathioprine Action Pathway		Not Available
Azathioprine Metabolism Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C16621

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

18209

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for 1-Methyl-4-nitroimidazole (HMDB0060659)

MOL for HMDB0060659 (1-Methyl-4-nitroimidazole)

3D MOL for HMDB0060659 (1-Methyl-4-nitroimidazole)

3D SDF for HMDB0060659 (1-Methyl-4-nitroimidazole)

3D-SDF for HMDB0060659 (1-Methyl-4-nitroimidazole)

PDB for HMDB0060659 (1-Methyl-4-nitroimidazole)

3D PDB for HMDB0060659 (1-Methyl-4-nitroimidazole)

SMILES for HMDB0060659 (1-Methyl-4-nitroimidazole)

INCHI for HMDB0060659 (1-Methyl-4-nitroimidazole)

Structure for HMDB0060659 (1-Methyl-4-nitroimidazole)

3D Structure for HMDB0060659 (1-Methyl-4-nitroimidazole)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra