Showing Compound Imidazole (FDB012307)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:06 UTC

Update date

2019-11-26 03:06:33 UTC

Primary ID

FDB012307

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Imidazole

Description

Isolated from the seeds of Lens culinaris (lentil)and is also present in the seeds of other legumes: Macrotyloma uniflorum (horse gram), Psophocarpus tetragonolobus (winged bean), Vigna radiata (mung bean) Imidazole is a 5-membered planar ring, which is soluble in water and other polar solvents. It exists in two equivalent tautomeric forms because the hydrogen atom can be located on either of the two nitrogen atoms. Imidazole is a highly polar compound, as evidenced by a calculated dipole of 3.61D, and is entirely soluble in water. The compound is classified as aromatic due to the presence of a sextet of ?-electrons, consisting of a pair of electrons from the protonated nitrogen atom and one from each of the remaining four atoms of the ring.; Imidazole is a heterocyclic aromatic organic compound. It is further classified as an alkaloid. Imidazole refers to the parent compound C3H4N2, while imidazoles are a class of heterocycles with similar ring structure but varying substituents. This ring system is present in important biological building blocks such as histidine and histamine. Imidazole can act as a base and as a weak acid. Imidazole exists in two tautomeric forms with the hydrogen atom moving between the two nitrogens. Many drugs contain an imidazole ring, such as antifungal drugs and nitroimidazole. Imidazole is a 5 membered planar ring which is soluble in water and polar solvents. Imidazole is a base and an excellent nucleophile. It reacts at the NH nitrogen, attacking alkylating and acylating compounds. It is not particularly susceptible to electrophilic attacks at the carbon atoms, and most of these reactions are substitutions that keep the aromaticity intact. One can see from the resonance structure that the carbon-2 is the carbon most likely to have a nucleophile attack it, but in general nucleophilic substitutions are difficult with imidazole. Imidazole is incorporated into many important biological molecules. The most obvious is the amino acid histidine, which has an imidazole side chain. histidine is present in many proteins and enzymes and plays a vital part in the structure and binding functions of hemoglobin.; Imidazole is an organic compound with the formula C3H4N2. This aromatic heterocyclic is classified as an alkaloid. Imidazole refers to the parent compound whereas imidazoles are a class of heterocycles with similar ring structure but varying substituents. This ring system is present in important biological building blocks such as histidine, and the related hormone histamine. Imidazole can serve as a base and as a weak acid. Many drugs contain an imidazole ring, such as antifungal drugs and nitroimidazole.; Imidazole is incorporated into many important biological molecules. The most pervasive is the amino acid histidine, which has an imidazole side chain. Histidine is present in many proteins and enzymes and plays a vital part in the structure and binding functions of hemoglobin. Histidine can be decarboxylated to histamine, which is also a common biological compound. It is a component of the toxin that causes urticaria, which is another name for allergic hives. The relationship between histidine and histamine are shown below:; This is a general method which is able to give good yields for substituted imidazoles. It is essentially an adaptation of the Debus method called the Debus-Radziszewski imidazole synthesis. The starting materials are substituted glyoxal, aldehyde, amine, and ammonia or an ammonium salt. Imidazole is found in pulses.

CAS Number

288-32-4

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
1,3-Diaza-2,4-cyclopentadiene	ChEBI
1,3-Diazole	ChEBI
Glyoxaline	ChEBI
Him	ChEBI
IMD	ChEBI
Imidazol	ChEBI
Iminazole	ChEBI
Miazole	ChEBI
N,N'-1,2-ethenediylmethanimidamide	ChEBI
N,N'-vinyleneformamidine	ChEBI
Pyrro[b]monazole	ChEBI
1H-Imidazole	HMDB
Glyoxalin	HMDB
Imutex	HMDB
Pyrro(b)monazole	HMDB
{Pyrro[b]monazole}	HMDB
Imidazole acetate	HMDB
Imidazole monophosphonate	HMDB
Imidazole sodium	HMDB
Imidazolium chloride	HMDB
Al-imidazole	HMDB
Imidazole citrate	HMDB
Cu-imidazole	HMDB
Imidazole conjugate monoacid	HMDB
Imidazole monohydrochloride	HMDB
Imidazole	ChEBI
1,3-Diaza-2,4-cyclopentadiene-	biospider
1467-16-9 (mono-hydrochloride)	biospider
1H-Imidazole (9CI)	biospider
Formamidine, n,n'-vinylene-	biospider
Glioksal	biospider
HIM	biospider
Imidazole (8CI)	biospider
Imidazole-ring	biospider
Methanimidamide, N,N'-1, 2-ethenediyl-	biospider
Methanimidamide, N,N'-1,2-ethenediyl-	biospider
N,n'-vinyleneformamidine	biospider

Predicted Properties

Property	Value	Source
Water Solubility	538 g/L	ALOGPS
logP	-0.21	ALOGPS
logP	-0.15	ChemAxon
logS	0.9	ALOGPS
pKa (Strongest Acidic)	13.4	ChemAxon
pKa (Strongest Basic)	6.97	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	28.68 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	19.01 m³·mol⁻¹	ChemAxon
Polarizability	6.56 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C3H4N2

IUPAC name

1H-imidazole

InChI Identifier

InChI=1S/C3H4N2/c1-2-5-3-4-1/h1-3H,(H,4,5)

InChI Key

RAXXELZNTBOGNW-UHFFFAOYSA-N

Isomeric SMILES

N1C=CN=C1

Average Molecular Weight

68.0773

Monoisotopic Molecular Weight

68.037448138

Classification

Description

Belongs to the class of organic compounds known as imidazoles. Imidazoles are compounds containing an imidazole ring, which is an aromatic five-member ring with two nitrogen atoms at positions 1 and 3, and three carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azoles

Sub Class

Imidazoles

Direct Parent

Imidazoles

Alternative Parents

Substituents

Heteroaromatic compound
Imidazole
Azacycle
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

mancude organic heteromonocyclic parent (CHEBI:16069 )
monocyclic heteroarene (CHEBI:16069 )
imidazole (CHEBI:16069 )
an aromatic compound (IMIDAZOLE-RING )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Plant:

Fabaceae

Biological location:

Cell and elements:

Cell:

Nerve cell

Element:

Platelet

Organ and components:

Endocrine gland:

Tissue and substructures:

Subcellular:

Cytoplasm

Biofluid and excreta:

Urine

Role

Industrial application:

Drug

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 52.93%; H 5.92%; N 41.15%	DFC
Melting Point	Mp 88-90°	DFC
Boiling Point	Bp 255°	DFC
Experimental Water Solubility	Not Available
Experimental logP	-0.08	HANSCH,C ET AL. (1995)
Experimental pKa	pKa2 14.52 (25°,acidic)	DFC
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Imidazole, non-derivatized, GC-MS Spectrum	splash10-014l-9000000000-e6b2b7faf77dcf80d593	Spectrum
GC-MS	Imidazole, non-derivatized, GC-MS Spectrum	splash10-014l-9000000000-e6b2b7faf77dcf80d593	Spectrum
Predicted GC-MS	Imidazole, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-014i-9000000000-ba9a75409716dbd6ae14	Spectrum
Predicted GC-MS	Imidazole, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-014l-9000000000-2ca95342014cfc85bb74	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-014i-9000000000-7d24c7b22fb67b2a5b76	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-014l-9000000000-f50f9a9c83174e9c149f	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive	splash10-014l-9000000000-e6b2b7faf77dcf80d593	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-014i-9000000000-76b001eeacbb900271fa	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-014i-9000000000-5398a23c5b95419a1e5b	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-014i-9000000000-ad715dac27bd6d79523d	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-014i-9000000000-9dad13fc804c087084a8	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-014i-9000000000-36c1868da6ae549e0d51	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-014i-9000000000-76b001eeacbb900271fa	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-014i-9000000000-5398a23c5b95419a1e5b	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-014i-9000000000-ad715dac27bd6d79523d	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-014i-9000000000-9dad13fc804c087084a8	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-014l-9000000000-36c1868da6ae549e0d51	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-014i-9000000000-0b1bce58fb1f7bcc7093	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-014l-9000000000-1e75707c493cc0d66885	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-9000000000-b3d4133417298a44a53b	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-9000000000-ec4b53ab61f0e52b88c1	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-eff641f0ad5995348cb6	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-9000000000-e5fe87bd22a87dc81aaf	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-9000000000-e5fe87bd22a87dc81aaf	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-984396e105296a5464dd	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-9000000000-985af79883cf80d0af6b	2017-07-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-9000000000-d6f5b271615f8e978a66	2017-07-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014l-9000000000-4f888ed0233af45d54e5	2017-07-25	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Methanol, experimental)	Spectrum
2D NMR	[¹H, ¹H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 400 MHz, H₂O, experimental)	Spectrum