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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2006-05-22 14:17:45 UTC

Update Date

2023-02-21 17:16:18 UTC

HMDB ID

HMDB0002271

Secondary Accession Numbers

HMDB02271

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

View in JSmol View NMR Assignments View Stereo Labels

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 )

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

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	206 - 208 °C	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
Water Solubility	43.9 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	131.404	31661259
DarkChem	[M-H]-	125.222	31661259
DeepCCS	[M+H]+	126.678	30932474
DeepCCS	[M-H]-	123.545	30932474
DeepCCS	[M-2H]-	160.568	30932474
DeepCCS	[M+Na]+	135.502	30932474
AllCCS	[M+H]+	130.5	32859911
AllCCS	[M+H-H2O]+	126.0	32859911
AllCCS	[M+NH4]+	134.7	32859911
AllCCS	[M+Na]+	135.9	32859911
AllCCS	[M-H]-	127.3	32859911
AllCCS	[M+Na-2H]-	129.0	32859911
AllCCS	[M+HCOO]-	130.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Imidazolepropionic acid	OC(=O)CCC1=CNC=N1	2714.5	Standard polar	33892256
Imidazolepropionic acid	OC(=O)CCC1=CNC=N1	1348.4	Standard non polar	33892256
Imidazolepropionic acid	OC(=O)CCC1=CNC=N1	1657.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Imidazolepropionic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)CCC1=C[NH]C=N1	1490.0	Semi standard non polar	33892256
Imidazolepropionic acid,1TMS,isomer #2	C[Si](C)(C)N1C=NC(CCC(=O)O)=C1	1742.5	Semi standard non polar	33892256
Imidazolepropionic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)CCC1=CN([Si](C)(C)C)C=N1	1744.1	Semi standard non polar	33892256
Imidazolepropionic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)CCC1=CN([Si](C)(C)C)C=N1	1639.0	Standard non polar	33892256
Imidazolepropionic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)CCC1=CN([Si](C)(C)C)C=N1	1997.9	Standard polar	33892256
Imidazolepropionic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCC1=C[NH]C=N1	1726.6	Semi standard non polar	33892256
Imidazolepropionic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C=NC(CCC(=O)O)=C1	2008.0	Semi standard non polar	33892256
Imidazolepropionic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCC1=CN([Si](C)(C)C(C)(C)C)C=N1	2223.6	Semi standard non polar	33892256
Imidazolepropionic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCC1=CN([Si](C)(C)C(C)(C)C)C=N1	2081.6	Standard non polar	33892256
Imidazolepropionic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCC1=CN([Si](C)(C)C(C)(C)C)C=N1	2166.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Imidazolepropionic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-000y-9200000000-8af7c94edf62d10d7905	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Imidazolepropionic acid GC-MS (1 TMS) - 70eV, Positive	splash10-00dj-9200000000-466ffc1c8385b5811677	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Imidazolepropionic acid 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Imidazolepropionic acid CE-QTOF-MS system (Agilent 7100 CE + 6550 QTOF) 20V, Positive-QTOF	splash10-0006-0900000000-593be5cf10aba06261f0	2019-03-07	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imidazolepropionic acid 10V, Positive-QTOF	splash10-006x-1900000000-f813e755bd0c33989b99	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imidazolepropionic acid 20V, Positive-QTOF	splash10-006t-9700000000-fc60958d4ee5d49335ca	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imidazolepropionic acid 40V, Positive-QTOF	splash10-0gb9-9000000000-c8f93079184c6ee4b5d8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imidazolepropionic acid 10V, Negative-QTOF	splash10-000i-2900000000-684a7e6823977a73c2b4	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imidazolepropionic acid 20V, Negative-QTOF	splash10-000j-6900000000-3f4fc2398941bf5c7395	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imidazolepropionic acid 40V, Negative-QTOF	splash10-05mo-9100000000-49b8e29531a2099a80ce	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imidazolepropionic acid 10V, Negative-QTOF	splash10-000b-9400000000-f2cb4a7574ec2ba4ce92	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imidazolepropionic acid 20V, Negative-QTOF	splash10-014j-9100000000-8e37d715ddc9ef376bf7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imidazolepropionic acid 40V, Negative-QTOF	splash10-014l-9000000000-2ee2f80749be6e61f757	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imidazolepropionic acid 10V, Positive-QTOF	splash10-00dl-5900000000-bb071711eca6657a6d91	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imidazolepropionic acid 20V, Positive-QTOF	splash10-0002-9100000000-4bbf16992517da7c64f6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imidazolepropionic acid 40V, Positive-QTOF	splash10-014l-9000000000-fe8160b6c4b3de352e44	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	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]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Feces
Saliva
Urine

Tissue Locations

Placenta

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	27015276	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	25037050	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Supragingival Plaque	31026179	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

Associated Disorders and Diseases

Disease References

Colorectal cancer
Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ] Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ] Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
Supragingival Plaque
Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]

Associated OMIM IDs

114500 (Colorectal cancer)

External Links

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

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

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.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Block WD, Westhoff MH, Steele BF: Histidine metabolism in the human adult: histidine blood tolerance, and the effect of continued free L-histidine ingestion on the concentration of imidazole compounds in blood and urine. J Nutr. 1967 Feb;91(2):189-94. [PubMed:6021220 ]
Antener I, Verwilghen AM, Van Geert C, Mauron J: Biochemical study of malnutrition. Part VI: Histidine and its metabolites. Int J Vitam Nutr Res. 1983;53(2):199-209. [PubMed:6136484 ]
SEN NP, McGEER PL, PAUL RM: Imidazolepropionic acid as a urinary metabolite of L-histidine. Biochem Biophys Res Commun. 1962 Oct 17;9:257-61. [PubMed:13987921 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Showing metabocard for Imidazolepropionic acid (HMDB0002271)

MOL for HMDB0002271 (Imidazolepropionic acid)

3D MOL for HMDB0002271 (Imidazolepropionic acid)

3D SDF for HMDB0002271 (Imidazolepropionic acid)

3D-SDF for HMDB0002271 (Imidazolepropionic acid)

PDB for HMDB0002271 (Imidazolepropionic acid)

3D PDB for HMDB0002271 (Imidazolepropionic acid)

SMILES for HMDB0002271 (Imidazolepropionic acid)

INCHI for HMDB0002271 (Imidazolepropionic acid)

Structure for HMDB0002271 (Imidazolepropionic acid)

3D Structure for HMDB0002271 (Imidazolepropionic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra