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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2017-03-23 04:25:14 UTC
Update Date2022-03-07 03:17:56 UTC
HMDB IDHMDB0062562
Secondary Accession Numbers
  • HMDB62562
Metabolite Identification
Common NameTrans-urocanate
Descriptionurocanic acid, also known as urocanate, 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. An alpha,beta-unsaturated monocarboxylic acid that is prop-2-enoic acid substituted by a 1H-imidazol-4-yl group at position 3. urocanic acid is a very strong basic compound (based on its pKa).
Structure
Data?1563866329
Synonyms
ValueSource
3-(1H-Imidazol-4-yl)-2-propenoic acidChEBI
3-Imidazol-4-ylacrylic acidChEBI
3-(1H-Imidazol-4-yl)-2-propenoateGenerator
3-Imidazol-4-ylacrylateGenerator
UrocanateGenerator
trans-Urocanic acidGenerator
Chemical FormulaC6H6N2O2
Average Molecular Weight138.126
Monoisotopic Molecular Weight138.042927441
IUPAC Name3-(1H-imidazol-5-yl)prop-2-enoic acid
Traditional Nameurocanic acid
CAS Registry NumberNot Available
SMILES
OC(=O)C=CC1=CN=CN1
InChI Identifier
InChI=1S/C6H6N2O2/c9-6(10)2-1-5-3-7-4-8-5/h1-4H,(H,7,8)(H,9,10)
InChI KeyLOIYMIARKYCTBW-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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzoles
Sub ClassImidazoles
Direct ParentImidazolyl 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 FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility255 g/lALOGPS
LogP-0.16ALOGPS
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP0ALOGPS
logP-0.86ChemAxon
logS-0.82ALOGPS
pKa (Strongest Acidic)3.91ChemAxon
pKa (Strongest Basic)6.83ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area65.98 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity35.89 m³·mol⁻¹ChemAxon
Polarizability12.8 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+131.02731661259
DarkChem[M-H]-123.85431661259
DeepCCS[M+H]+126.56130932474
DeepCCS[M-H]-123.33530932474
DeepCCS[M-2H]-160.50330932474
DeepCCS[M+Na]+135.62830932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Trans-urocanateOC(=O)C=CC1=CN=CN12784.0Standard polar33892256
Trans-urocanateOC(=O)C=CC1=CN=CN11873.8Standard non polar33892256
Trans-urocanateOC(=O)C=CC1=CN=CN11783.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Trans-urocanate,1TMS,isomer #1C[Si](C)(C)OC(=O)C=CC1=CN=C[NH]11716.6Semi standard non polar33892256
Trans-urocanate,1TMS,isomer #2C[Si](C)(C)N1C=NC=C1C=CC(=O)O1844.7Semi standard non polar33892256
Trans-urocanate,2TMS,isomer #1C[Si](C)(C)OC(=O)C=CC1=CN=CN1[Si](C)(C)C1840.6Semi standard non polar33892256
Trans-urocanate,2TMS,isomer #1C[Si](C)(C)OC(=O)C=CC1=CN=CN1[Si](C)(C)C1851.2Standard non polar33892256
Trans-urocanate,2TMS,isomer #1C[Si](C)(C)OC(=O)C=CC1=CN=CN1[Si](C)(C)C2093.5Standard polar33892256
Trans-urocanate,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C=CC1=CN=C[NH]11971.5Semi standard non polar33892256
Trans-urocanate,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C=NC=C1C=CC(=O)O2075.8Semi standard non polar33892256
Trans-urocanate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C=CC1=CN=CN1[Si](C)(C)C(C)(C)C2330.8Semi standard non polar33892256
Trans-urocanate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C=CC1=CN=CN1[Si](C)(C)C(C)(C)C2256.4Standard non polar33892256
Trans-urocanate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C=CC1=CN=CN1[Si](C)(C)C(C)(C)C2279.0Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Trans-urocanate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Trans-urocanate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trans-urocanate 10V, Positive-QTOFsplash10-00di-0900000000-84f41e622422f6694e482019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trans-urocanate 20V, Positive-QTOFsplash10-006x-7900000000-35f4781a887c4ee85b952019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trans-urocanate 40V, Positive-QTOFsplash10-0f96-9000000000-2dddf68bdc9cd729aac22019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trans-urocanate 10V, Negative-QTOFsplash10-000i-1900000000-97582b33fae8aefd78112019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trans-urocanate 20V, Negative-QTOFsplash10-00ku-3900000000-4c30c1a99fa8de8a35222019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trans-urocanate 40V, Negative-QTOFsplash10-00kf-9200000000-377ee8a62816e7531acd2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trans-urocanate 10V, Positive-QTOFsplash10-00di-0900000000-8a1dddb6aabb5fb9243f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trans-urocanate 20V, Positive-QTOFsplash10-006x-9700000000-caeb8bd53eb25b9ce23b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trans-urocanate 40V, Positive-QTOFsplash10-00kf-9000000000-d7b02bc4401175bbfed32021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trans-urocanate 10V, Negative-QTOFsplash10-0006-9100000000-058e97cab302e3106c142021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trans-urocanate 20V, Negative-QTOFsplash10-00kf-9000000000-08715a8e8b2dbb40dead2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trans-urocanate 40V, Negative-QTOFsplash10-014l-9000000000-6f3eeca7a7e40dd721e62021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MaleAttachment loss  details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MaleMissing teeth details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MalePeriodontal Probing Depth details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. 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 ]
  2. 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 ]
Attachment loss
  1. 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 ]
Missing teeth
  1. 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 ]
Periodontal Probing Depth
  1. 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
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDUROCANATE
BiGG IDNot Available
Wikipedia LinkUrocanic_acid
METLIN IDNot Available
PubChem Compound1178
PDB IDNot Available
ChEBI ID27248
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available