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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:31:00 UTC

Update Date

2023-02-21 17:23:35 UTC

HMDB ID

HMDB0033755

Secondary Accession Numbers

HMDB33755

Metabolite Identification

Common Name

2-Butyl-1H-benzimidazole

Description

2-Butyl-1H-benzimidazole belongs to the class of organic compounds known as benzimidazoles. These are organic compounds containing a benzene ring fused to an imidazole ring (five member ring containing a nitrogen atom, 4 carbon atoms, and two double bonds). 2-Butyl-1H-benzimidazole has been detected, but not quantified in, eggs. This could make 2-butyl-1H-benzimidazole a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 2-Butyl-1H-benzimidazole.

Structure

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

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -3.400   5.510   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.630   4.176   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.090   4.176   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.320   2.843   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       2.126   1.597   0.000  0.00  0.00           N+0
HETATM   13  N   UNK     0       2.126   4.089   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    8                                                       
CONECT    4    5    6                                                       
CONECT    5    4    7                                                       
CONECT    6    4    9                                                       
CONECT    7    5   10                                                       
CONECT    8    3   11                                                       
CONECT    9    6   10   12                                                  
CONECT   10    7    9   13                                                  
CONECT   11    8   12   13                                                  
CONECT   12    9   11                                                       
CONECT   13   10   11                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

COMPND    HMDB0033755
HETATM    1  C1  UNL     1       4.122   1.139  -0.238  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.682  -0.255   0.131  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.209  -0.369   0.352  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.408   0.009  -0.878  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.060  -0.119  -0.613  1.00  0.00           C  
HETATM    6  N1  UNL     1      -0.830  -1.215  -0.802  1.00  0.00           N  
HETATM    7  C6  UNL     1      -2.100  -0.950  -0.452  1.00  0.00           C  
HETATM    8  C7  UNL     1      -3.283  -1.641  -0.426  1.00  0.00           C  
HETATM    9  C8  UNL     1      -4.466  -1.095  -0.005  1.00  0.00           C  
HETATM   10  C9  UNL     1      -4.507   0.219   0.422  1.00  0.00           C  
HETATM   11  C10 UNL     1      -3.336   0.940   0.408  1.00  0.00           C  
HETATM   12  C11 UNL     1      -2.153   0.379  -0.018  1.00  0.00           C  
HETATM   13  N2  UNL     1      -0.890   0.825  -0.138  1.00  0.00           N  
HETATM   14  H1  UNL     1       3.577   1.921   0.325  1.00  0.00           H  
HETATM   15  H2  UNL     1       4.081   1.305  -1.345  1.00  0.00           H  
HETATM   16  H3  UNL     1       5.199   1.220   0.030  1.00  0.00           H  
HETATM   17  H4  UNL     1       4.045  -0.925  -0.694  1.00  0.00           H  
HETATM   18  H5  UNL     1       4.237  -0.560   1.028  1.00  0.00           H  
HETATM   19  H6  UNL     1       1.932   0.211   1.237  1.00  0.00           H  
HETATM   20  H7  UNL     1       1.985  -1.432   0.578  1.00  0.00           H  
HETATM   21  H8  UNL     1       1.650   1.014  -1.244  1.00  0.00           H  
HETATM   22  H9  UNL     1       1.650  -0.711  -1.683  1.00  0.00           H  
HETATM   23  H10 UNL     1      -3.302  -2.675  -0.752  1.00  0.00           H  
HETATM   24  H11 UNL     1      -5.401  -1.645   0.015  1.00  0.00           H  
HETATM   25  H12 UNL     1      -5.450   0.645   0.755  1.00  0.00           H  
HETATM   26  H13 UNL     1      -3.388   1.962   0.745  1.00  0.00           H  
HETATM   27  H14 UNL     1      -0.609   1.802   0.114  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3   17   18
CONECT    3    4   19   20
CONECT    4    5   21   22
CONECT    5    6    6   13
CONECT    6    7
CONECT    7    8    8   12
CONECT    8    9   23
CONECT    9   10   10   24
CONECT   10   11   25
CONECT   11   12   12   26
CONECT   12   13
CONECT   13   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Butyl-benzimidazole	HMDB
2-Butylbenzimidazole	HMDB

Chemical Formula

C₁₁H₁₄N₂

Average Molecular Weight

174.2423

Monoisotopic Molecular Weight

174.115698458

IUPAC Name

2-butyl-1H-1,3-benzodiazole

Traditional Name

2-butyl-1H-1,3-benzodiazole

CAS Registry Number

5851-44-5

SMILES

CCCCC1=NC2=CC=CC=C2N1

InChI Identifier

InChI=1S/C11H14N2/c1-2-3-8-11-12-9-6-4-5-7-10(9)13-11/h4-7H,2-3,8H2,1H3,(H,12,13)

InChI Key

HITWHALOZBMLHY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzimidazoles. These are organic compounds containing a benzene ring fused to an imidazole ring (five member ring containing a nitrogen atom, 4 carbon atoms, and two double bonds).

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzimidazoles

Sub Class

Not Available

Direct Parent

Benzimidazoles

Alternative Parents

Substituents

Benzimidazole
Benzenoid
Heteroaromatic compound
Imidazole
Azole
Azacycle
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0033755)
Cell membrane (HMDB: HMDB0033755)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033755)

Source

Exogenous

Exogenous (HMDB: HMDB0033755)

Food

Food (HMDB: HMDB0033755)

Egg

Eggs (FooDB: FOOD00619)

Endogenous

Animal

Animal (HMDB: HMDB0033755)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0033755)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	153 - 154 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	97.43 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.52 g/L	ALOGPS
logP	3.63	ALOGPS
logP	2.97	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	12.55	ChemAxon
pKa (Strongest Basic)	6.18	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	28.68 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	53.24 m³·mol⁻¹	ChemAxon
Polarizability	20.9 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	139.631	31661259
DarkChem	[M-H]-	140.977	31661259
DeepCCS	[M+H]+	136.474	30932474
DeepCCS	[M-H]-	132.615	30932474
DeepCCS	[M-2H]-	169.797	30932474
DeepCCS	[M+Na]+	145.373	30932474
AllCCS	[M+H]+	139.9	32859911
AllCCS	[M+H-H2O]+	135.7	32859911
AllCCS	[M+NH4]+	143.9	32859911
AllCCS	[M+Na]+	145.1	32859911
AllCCS	[M-H]-	143.4	32859911
AllCCS	[M+Na-2H]-	144.0	32859911
AllCCS	[M+HCOO]-	144.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Butyl-1H-benzimidazole	CCCCC1=NC2=CC=CC=C2N1	2460.4	Standard polar	33892256
2-Butyl-1H-benzimidazole	CCCCC1=NC2=CC=CC=C2N1	1680.8	Standard non polar	33892256
2-Butyl-1H-benzimidazole	CCCCC1=NC2=CC=CC=C2N1	1770.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Butyl-1H-benzimidazole,1TMS,isomer #1	CCCCC1=NC2=CC=CC=C2N1[Si](C)(C)C	1800.3	Semi standard non polar	33892256
2-Butyl-1H-benzimidazole,1TMS,isomer #1	CCCCC1=NC2=CC=CC=C2N1[Si](C)(C)C	1685.5	Standard non polar	33892256
2-Butyl-1H-benzimidazole,1TBDMS,isomer #1	CCCCC1=NC2=CC=CC=C2N1[Si](C)(C)C(C)(C)C	2040.5	Semi standard non polar	33892256
2-Butyl-1H-benzimidazole,1TBDMS,isomer #1	CCCCC1=NC2=CC=CC=C2N1[Si](C)(C)C(C)(C)C	1908.5	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Butyl-1H-benzimidazole GC-MS (Non-derivatized) - 70eV, Positive	splash10-003u-5900000000-ce9d41781d5704f8b142	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Butyl-1H-benzimidazole GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Butyl-1H-benzimidazole 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 - 2-Butyl-1H-benzimidazole 10V, Positive-QTOF	splash10-004i-0900000000-2ccce8f31236c7eeeb32	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Butyl-1H-benzimidazole 20V, Positive-QTOF	splash10-004i-1900000000-1d5bab2eeea32baeaceb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Butyl-1H-benzimidazole 40V, Positive-QTOF	splash10-0006-9400000000-2d1e208453d84dd437ff	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Butyl-1H-benzimidazole 10V, Negative-QTOF	splash10-00di-0900000000-fb0fe25e0ee3500a92ec	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Butyl-1H-benzimidazole 20V, Negative-QTOF	splash10-00di-0900000000-cff929a3272926bd21ac	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Butyl-1H-benzimidazole 40V, Negative-QTOF	splash10-05qa-3900000000-6ebfea0f91e5b0a29475	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Butyl-1H-benzimidazole 10V, Negative-QTOF	splash10-00di-0900000000-7bf47db63971154d9fbc	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Butyl-1H-benzimidazole 20V, Negative-QTOF	splash10-00di-0900000000-0f751bc9034138c0205a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Butyl-1H-benzimidazole 40V, Negative-QTOF	splash10-00kf-7900000000-6fae2cfe91a157d556da	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Butyl-1H-benzimidazole 10V, Positive-QTOF	splash10-004i-0900000000-ca91ad942a98700cc47b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Butyl-1H-benzimidazole 20V, Positive-QTOF	splash10-004i-0900000000-6558276a478d05886849	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Butyl-1H-benzimidazole 40V, Positive-QTOF	splash10-001i-6900000000-4159d5c687816b8aa51c	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+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

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

FDB011890

KNApSAcK ID

Not Available

Chemspider ID

20781

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

22122

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1838201

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 2-Butyl-1H-benzimidazole (HMDB0033755)

MOL for HMDB0033755 (2-Butyl-1H-benzimidazole)

3D MOL for HMDB0033755 (2-Butyl-1H-benzimidazole)

3D SDF for HMDB0033755 (2-Butyl-1H-benzimidazole)

3D-SDF for HMDB0033755 (2-Butyl-1H-benzimidazole)

PDB for HMDB0033755 (2-Butyl-1H-benzimidazole)

3D PDB for HMDB0033755 (2-Butyl-1H-benzimidazole)

SMILES for HMDB0033755 (2-Butyl-1H-benzimidazole)

INCHI for HMDB0033755 (2-Butyl-1H-benzimidazole)

Structure for HMDB0033755 (2-Butyl-1H-benzimidazole)

3D Structure for HMDB0033755 (2-Butyl-1H-benzimidazole)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra