MiMeDB: Showing metabocard for Imidazolepropionic acid (MMDBc0000412)

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Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:37:11 UTC

Update Date

2024-04-30 19:32:18 UTC

Metabolite ID

MMDBc0000412

Metabolite Identification

Common Name

Imidazolepropionic acid

Description

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 3D MOL SDF 3D SDF PDB 3D 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

Molecular Formula

C₆H₈N₂O₂

Average Mass

140.1399

Monoisotopic Mass

140.05857751

IUPAC Name

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

Traditional Name

5-imidazolepropionic acid

CAS Registry Number

Not Available

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

Functional Ontology

Physical Properties

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-000y-9200000000-8af7c94edf62d10d7905	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00dj-9200000000-466ffc1c8385b5811677	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - CE-QTOF-MS system (Agilent 7100 CE + 6550 QTOF) 20V, Positive	splash10-0006-0900000000-593be5cf10aba06261f0	2019-03-07	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-006x-1900000000-f813e755bd0c33989b99	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-006t-9700000000-fc60958d4ee5d49335ca	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gb9-9000000000-c8f93079184c6ee4b5d8	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-2900000000-684a7e6823977a73c2b4	2016-08-04	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000j-6900000000-3f4fc2398941bf5c7395	2016-08-04	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05mo-9100000000-49b8e29531a2099a80ce	2016-08-04	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000b-9400000000-f2cb4a7574ec2ba4ce92	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014j-9100000000-8e37d715ddc9ef376bf7	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014l-9000000000-2ee2f80749be6e61f757	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00dl-5900000000-bb071711eca6657a6d91	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9100000000-4bbf16992517da7c64f6	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014l-9000000000-fe8160b6c4b3de352e44	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum

Biological Properties

Human Proteins and Enzymes

Human Pathways

Metabolic Reactions

Health Effects and Bioactivity

Microbial Sources

Exposure Sources

Host Biospecimen and Location

External Links

References

Showing metabocard for Imidazolepropionic acid (MMDBc0000412)

MOL for #<Metabolite:0x00007fd5cc1ab9a0>

3D MOL for #<Metabolite:0x00007fd5cc1ab9a0>

3D SDF for #<Metabolite:0x00007fd5cc1ab9a0>

3D-SDF for #<Metabolite:0x00007fd5cc1ab9a0>

PDB for #<Metabolite:0x00007fd5cc1ab9a0>

3D PDB for #<Metabolite:0x00007fd5cc1ab9a0>

SMILES for #<Metabolite:0x00007fd5cc1ab9a0>

INCHI for #<Metabolite:0x00007fd5cc1ab9a0>

Structure for #<Metabolite:0x00007fd5cc1ab9a0>

3D Structure for #<Metabolite:0x00007fd5cc1ab9a0>