ChemFOnt: Showing chemical card for Imidazolepropionic acid (CFc000001531)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:46:11 UTC

Chemfont ID

CFc000001531

Molecule Identification

Common Name

Imidazolepropionic acid

Definition

Imidazolepropionic acid, also known as deaminohistidine or 4-imidazolylpropionate (ImP), belongs to the class of organic compounds known as imidazolyl carboxylic acids and derivatives. These are organic compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an imidazole ring. ImP is a metabolite of histidine and it is formed from histidine via a urocanate intermediate in gut microbiota by the enzyme urocanate reductase (urdA). ImP is a very strong basic compound (based on its pKa). ImP is a product of histidine metabolism which may involve oxidation or transamination. This compound is found in the urine of rats loaded with histidine (PMID: 6021220 ). ImP (100 µM) decreases protein levels of insulin receptor substrate 1 (IRS-1), IRS-2, and phosphorylated Akt and increases levels of the mTORC1 activation marker phosphorylated p70 ribosomal S6 kinase enzyme (p70S6K) in primary mouse hepatocytes. It induces deficits in glucose tolerance in germ-free and conventionally raised mice when administered at doses of 500 and 100 µg/animal, respectively. It has also been found to prevent reductions in blood glucose levels induced by Metformin - a first-line therapy for type 2 diabetes - in mice (PMID: 33208748 , PMID: 32783890 , PMID: 30401435 ). Microbiota-host-diet interactions are known to contribute to the development of metabolic diseases and ImP is a known such microbially produced metabolic derivative histidine that impairs the mechanism of glucose. Specifically, ImP is found to be elevated in serum of individuals with pre-diabetes and diabetes (PMID: 33208748 ). Those with type 2 diabetes are shown to have significantly increased levels of serum ImP [0.028 μM (0.016–0.059) median and interquartile range; n = 140] compared to subjects with prediabetes [0.028 μM (0.017–0.049) median and interquartile range; n = 654] or normal glucose tolerance [0.020 μM (0.013–0.033) median and interquartile range; n = 359] (PMID: 33208748 ). ImP is also found to be elevated in serum of individuals with cardiovascular disease (CVD) (PMID: 33208748 ). ImP levels were significantly increased in CVD individuals [0.037 μM (0.021–0.069) median and interquartile range; n = 390] compared to individuals without CVD [0.025 μM (0.015–0.048) median and interquartile range; n = 1568] (P < 0.001, linear regression after adjustment for age, gender, BMI, ethnicity, diabetes status, and creatinine clearance) (PMID: 33208748 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1H-Imidazole-4-propanoic acid	ChEBI
3-(1H-Imidazol-4-yl)propionic acid	ChEBI
3-(Imidazol-4-yl)propanoic acid	ChEBI
3-(Imidazol-4-yl)propionic acid	ChEBI
4-Imidazolylpropanoic acid	ChEBI
4-Imidazolylpropionic acid	ChEBI
Deaminohistidine	ChEBI
Imidazolylpropionic acid	ChEBI
3-(1H-Imidazol-4-yl)propanoate	Kegg
1H-Imidazole-4-propanoate	Generator
3-(1H-Imidazol-4-yl)propionate	Generator
3-(Imidazol-4-yl)propanoate	Generator
3-(Imidazol-4-yl)propionate	Generator
4-Imidazolylpropanoate	Generator
4-Imidazolylpropionate	Generator
Imidazolylpropionate	Generator
3-(1H-Imidazol-4-yl)propanoic acid	Generator
Imidazolepropionate	Generator
3-(1H-Imidazol-4-yl)-propionate	HMDB
3-(1H-Imidazol-4-yl)-propionic acid	HMDB
5-Imidazolepropionate	HMDB
5-Imidazolepropionic acid	HMDB, MeSH
deamino-Histidine	HMDB
URO	HMDB
Imidazole propionate	MeSH, HMDB
Dihydrourocanate	Generator, HMDB
1H-Imidazole-4(5)-propanoate	Generator, HMDB
1H-Imidazole-4-propionic acid	HMDB
3-(1H-4-Imidazolyl)propanoic acid	HMDB
3-(1H-4-Imidazolyl)propionic acid	HMDB
3-(4-Imidazolyl)propanoic acid	HMDB
3-(4-Imidazolyl)propionic acid	HMDB
3-(Imidazol-4(5)-yl)propanoic acid	HMDB
3-(Imidazol-4(5)-yl)propionic acid	HMDB
5-(2-Carboxyethyl) imidazole	HMDB
Dihydrourocanic acid	HMDB
Dihydrourocanoic acid	HMDB
Imidazole-4(5)-propanoic acid	HMDB
Imidazole-4(5)-propionic acid	HMDB
Imidazole-4-propanoic acid	HMDB
Imidazole-4-propionic acid	HMDB
Imidazolylpropanoic acid	HMDB
beta-(5-Imidazolyl)propanoic acid	HMDB
beta-(5-Imidazolyl)propionic acid	HMDB
beta-Imidazolyl-4(5)-propanoic acid	HMDB
beta-Imidazolyl-4(5)-propionic acid	HMDB
β-(5-Imidazolyl)propanoic acid	HMDB
β-(5-Imidazolyl)propionic acid	HMDB
β-Imidazolyl-4(5)-propanoic acid	HMDB
β-Imidazolyl-4(5)-propionic acid	HMDB

Chemical Formula

C₆H₈N₂O₂

Average Molecular Weight

140.1399

Monoisotopic Molecular Weight

140.05857751

IUPAC Name

3-(1H-imidazol-5-yl)propanoic acid

Traditional Name

5-imidazolepropionic acid

CAS Registry Number

1074-59-5

SMILES

OC(=O)CCC1=CNC=N1

InChI Identifier

InChI=1S/C6H8N2O2/c9-6(10)2-1-5-3-7-4-8-5/h3-4H,1-2H2,(H,7,8)(H,9,10)

InChI Key

ZCKYOWGFRHAZIQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as imidazolyl carboxylic acids and derivatives. These are organic compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an imidazole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azoles

Sub Class

Imidazoles

Direct Parent

Imidazolyl carboxylic acids and derivatives

Alternative Parents

Substituents

Imidazolyl carboxylic acid derivative
Heteroaromatic compound
Azacycle
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

imidazolyl carboxylic acid (CHEBI:73087 )

Functional Ontology

Physiological effect

Health effect

Observation

Supragingival Plaque (HMDB: HMDB0002271)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0002271)
Saliva (PMID: 31026179)

Organ

Placenta (HMDB: HMDB0002271)

Excreta

Biofluid or Excreta

Feces (PMID: 27275383)

Source

Endogenous

Endogenous (HMDB: HMDB0002271)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Biomarker

Pregnancy (HMDB: HMDB0002271)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	45.9 g/L	ALOGPS
logP	-0.09	ALOGPS
logP	-1.1	ChemAxon
logS	-0.48	ALOGPS
pKa (Strongest Acidic)	4.04	ChemAxon
pKa (Strongest Basic)	6.77	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	65.98 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	34.95 m³·mol⁻¹	ChemAxon
Polarizability	13.59 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

External Links

HMDB ID

HMDB0002271

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6585

PubChem Compound

70630

PDB ID

Not Available

ChEBI ID

73087

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Akabori, Shiro. Synthesis of imidazole derivatives from a-amino acids. I. A new synthesis of desaminohistidine and a contribution to the knowledge of the constitution of ergothioneine. Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen (1933), 66B 151-8.

Showing chemical card for Imidazolepropionic acid (CFc000001531)

MOL for CFc000001531 (Imidazolepropionic acid)

3D MOL for CFc000001531 (Imidazolepropionic acid)

3D SDF for CFc000001531 (Imidazolepropionic acid)

3D-SDF for CFc000001531 (Imidazolepropionic acid)

PDB for CFc000001531 (Imidazolepropionic acid)

3D PDB for CFc000001531 (Imidazolepropionic acid)

SMILES for CFc000001531 (Imidazolepropionic acid)

INCHI for CFc000001531 (Imidazolepropionic acid)

Structure for CFc000001531 (Imidazolepropionic acid)

3D Structure for CFc000001531 (Imidazolepropionic acid)