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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 23:17:55 UTC

Update Date

2021-09-26 22:55:13 UTC

HMDB ID

HMDB0246267

Secondary Accession Numbers

None

Metabolite Identification

Common Name

4-Azabenzimidazole

Description

4-Azabenzimidazole, also known as 1-deazapurine or 3,4-diazaindole, belongs to the class of organic compounds known as imidazopyridines. These are organic polycyclic compounds containing an imidazole ring fused to a pyridine ring. Imidazole is 5-membered ring consisting of three carbon atoms, and two nitrogen centers at the 1- and 3-positions. Pyridine is a 6-membered ring consisting of five carbon atoms and one nitrogen center. Based on a literature review a significant number of articles have been published on 4-Azabenzimidazole. This compound has been identified in human blood as reported by (PMID: 31557052 ). 4-azabenzimidazole is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 4-Azabenzimidazole is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1-Deazapurine	ChEBI
3,4-Diazaindole	ChEBI
3H-Imidazo[4,5-b]pyridine	ChEBI
7-Azabenzimidazole	ChEBI
Azabenzimidazole	ChEBI
Pyrido(2,3-D)imidazole	ChEBI
1H-Imidazo(4,5-b)pyridine	HMDB

Chemical Formula

C₆H₅N₃

Average Molecular Weight

119.127

Monoisotopic Molecular Weight

119.048347173

IUPAC Name

1H-imidazo[4,5-b]pyridine

Traditional Name

3H-imidazo[4,5-b]pyridine

CAS Registry Number

Not Available

SMILES

N1C=NC2=C1C=CC=N2

InChI Identifier

InChI=1S/C6H5N3/c1-2-5-6(7-3-1)9-4-8-5/h1-4H,(H,7,8,9)

InChI Key

GAMYYCRTACQSBR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as imidazopyridines. These are organic polycyclic compounds containing an imidazole ring fused to a pyridine ring. Imidazole is 5-membered ring consisting of three carbon atoms, and two nitrogen centers at the 1- and 3-positions. Pyridine is a 6-membered ring consisting of five carbon atoms and one nitrogen center.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Imidazopyridines

Sub Class

Not Available

Direct Parent

Imidazopyridines

Alternative Parents

Substituents

Imidazopyridine
Pyridine
Heteroaromatic compound
Imidazole
Azole
Azacycle
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

imidazopyridine (CHEBI:59952 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

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
logP	0.58	ALOGPS
logP	0.37	ChemAxon
logS	-0.43	ALOGPS
pKa (Strongest Acidic)	10.57	ChemAxon
pKa (Strongest Basic)	3.54	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	41.57 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	34.38 m³·mol⁻¹	ChemAxon
Polarizability	11.57 Å³	ChemAxon
Number of Rings	2	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
DeepCCS	[M+H]+	120.968	30932474
DeepCCS	[M-H]-	117.874	30932474
DeepCCS	[M-2H]-	154.527	30932474
DeepCCS	[M+Na]+	129.503	30932474
AllCCS	[M+H]+	122.9	32859911
AllCCS	[M+H-H2O]+	117.8	32859911
AllCCS	[M+NH4]+	127.6	32859911
AllCCS	[M+Na]+	129.0	32859911
AllCCS	[M-H]-	119.5	32859911
AllCCS	[M+Na-2H]-	121.0	32859911
AllCCS	[M+HCOO]-	122.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Azabenzimidazole	N1C=NC2=C1C=CC=N2	1959.6	Standard polar	33892256
4-Azabenzimidazole	N1C=NC2=C1C=CC=N2	1395.9	Standard non polar	33892256
4-Azabenzimidazole	N1C=NC2=C1C=CC=N2	1409.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Azabenzimidazole,1TMS,isomer #1	C[Si](C)(C)N1C=NC2=NC=CC=C21	1563.5	Semi standard non polar	33892256
4-Azabenzimidazole,1TMS,isomer #1	C[Si](C)(C)N1C=NC2=NC=CC=C21	1472.0	Standard non polar	33892256
4-Azabenzimidazole,1TMS,isomer #1	C[Si](C)(C)N1C=NC2=NC=CC=C21	2031.7	Standard polar	33892256
4-Azabenzimidazole,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C=NC2=NC=CC=C21	1800.5	Semi standard non polar	33892256
4-Azabenzimidazole,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C=NC2=NC=CC=C21	1676.4	Standard non polar	33892256
4-Azabenzimidazole,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C=NC2=NC=CC=C21	2144.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Azabenzimidazole GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-6900000000-56358c9fe320ff6beb5e	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Azabenzimidazole 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 - 4-Azabenzimidazole 10V, Positive-QTOF	splash10-00di-0900000000-ef10496369a91fe7fe11	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Azabenzimidazole 20V, Positive-QTOF	splash10-00di-0900000000-ef10496369a91fe7fe11	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Azabenzimidazole 40V, Positive-QTOF	splash10-00di-0900000000-ef10496369a91fe7fe11	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Azabenzimidazole 10V, Negative-QTOF	splash10-014i-0900000000-38ae963283fcac1f0a25	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Azabenzimidazole 20V, Negative-QTOF	splash10-014i-0900000000-38ae963283fcac1f0a25	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Azabenzimidazole 40V, Negative-QTOF	splash10-014i-4900000000-3db70a21e0270b07a70d	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	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

60828

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

67504

PDB ID

Not Available

ChEBI ID

59952

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for 4-Azabenzimidazole (HMDB0246267)

MOL for HMDB0246267 (4-Azabenzimidazole)

3D MOL for HMDB0246267 (4-Azabenzimidazole)

3D SDF for HMDB0246267 (4-Azabenzimidazole)

3D-SDF for HMDB0246267 (4-Azabenzimidazole)

PDB for HMDB0246267 (4-Azabenzimidazole)

3D PDB for HMDB0246267 (4-Azabenzimidazole)

SMILES for HMDB0246267 (4-Azabenzimidazole)

INCHI for HMDB0246267 (4-Azabenzimidazole)

Structure for HMDB0246267 (4-Azabenzimidazole)

3D Structure for HMDB0246267 (4-Azabenzimidazole)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra