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Showing Compound Imidazoleacrylic acid (FDB007506)

Record Information
Version1.0
Creation date2010-04-08 22:07:38 UTC
Update date2019-11-26 03:01:41 UTC
Primary IDFDB007506
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameImidazoleacrylic acid
DescriptionTrans-urocanic acid, also known as 4-imidazoleacrylic acid or urocanate, belongs to imidazolyl carboxylic acids and derivatives class of compounds. Those are organic compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an imidazole ring. Trans-urocanic acid is soluble (in water) and a weakly acidic compound (based on its pKa). Trans-urocanic acid can be found in mung bean, which makes trans-urocanic acid a potential biomarker for the consumption of this food product. Trans-urocanic acid can be found primarily in most biofluids, including sweat, feces, blood, and urine, as well as in human liver and skin tissues. Trans-urocanic acid exists in all living organisms, ranging from bacteria to humans. In humans, trans-urocanic acid is involved in the histidine metabolism. Trans-urocanic acid is also involved in a couple of metabolic disorders, which include ammonia recycling and histidinemia.
CAS Number3465-72-3
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility42.5 g/LALOGPS
logP0.22ALOGPS
logP-1ChemAxon
logS-0.51ALOGPS
pKa (Strongest Acidic)3.85ChemAxon
pKa (Strongest Basic)6.13ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area65.98 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity35.57 m³·mol⁻¹ChemAxon
Polarizability13.1 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC6H6N2O2
IUPAC name(2E)-3-(1H-imidazol-4-yl)prop-2-enoic acid
InChI IdentifierInChI=1S/C6H6N2O2/c9-6(10)2-1-5-3-7-4-8-5/h1-4H,(H,7,8)(H,9,10)/b2-1+
InChI KeyLOIYMIARKYCTBW-OWOJBTEDSA-N
Isomeric SMILESOC(=O)\C=C\C1=CNC=N1
Average Molecular Weight138.124
Monoisotopic Molecular Weight138.042927446
Classification
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

Route of exposure:

Source:

Biological location:

Role

Biological role:

Industrial application:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSImidazoleacrylic acid, 2 TMS, GC-MS Spectrumsplash10-014m-1930000000-25b091170cc3ea73bcf7Spectrum
GC-MSImidazoleacrylic acid, non-derivatized, GC-MS Spectrumsplash10-00l5-1930000000-5c3c875338a517d52729Spectrum
GC-MSImidazoleacrylic acid, 2 TMS, GC-MS Spectrumsplash10-00di-9410000000-b58e1b2cdd5c12a6ba24Spectrum
GC-MSImidazoleacrylic acid, 2 TMS, GC-MS Spectrumsplash10-0159-3950000000-433e50271e182f8408fdSpectrum
GC-MSImidazoleacrylic acid, non-derivatized, GC-MS Spectrumsplash10-000f-9200000000-cb7f9025a0f6adf740c1Spectrum
GC-MSImidazoleacrylic acid, non-derivatized, GC-MS Spectrumsplash10-014m-1930000000-25b091170cc3ea73bcf7Spectrum
GC-MSImidazoleacrylic acid, non-derivatized, GC-MS Spectrumsplash10-00l5-1930000000-5c3c875338a517d52729Spectrum
GC-MSImidazoleacrylic acid, non-derivatized, GC-MS Spectrumsplash10-00di-9410000000-b58e1b2cdd5c12a6ba24Spectrum
GC-MSImidazoleacrylic acid, non-derivatized, GC-MS Spectrumsplash10-0159-3950000000-433e50271e182f8408fdSpectrum
GC-MSImidazoleacrylic acid, non-derivatized, GC-MS Spectrumsplash10-014m-1930000000-3815ef1f1f386e091dc3Spectrum
GC-MSImidazoleacrylic acid, non-derivatized, GC-MS Spectrumsplash10-00dm-2900000000-aaefc749352097679e8fSpectrum
Predicted GC-MSImidazoleacrylic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000f-9500000000-7f0462e0ef244d2118a8Spectrum
Predicted GC-MSImidazoleacrylic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-6910000000-b1e081746388d0700ce0Spectrum
Predicted GC-MSImidazoleacrylic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSImidazoleacrylic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSImidazoleacrylic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSImidazoleacrylic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-3900000000-8c1c060d06c1ce3fb5f72012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00kf-9000000000-ae9de21d4642045fb96c2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014l-9000000000-8e6978d7f104386d2e822012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-000f-9200000000-cb7f9025a0f6adf740c12012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-000i-1900000000-c628b05706544cb1ebdc2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0006-9300000000-bc4c631410a5cbb3c2f52012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0006-9000000000-ccac569cbc78a632da482012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-9000000000-a22c861e4f2551a3f5822012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-00kf-9000000000-37421b473ba575d307fd2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-00du-5900000000-29dc15087c785a19c0ee2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0006-9200000000-1cc9b0a66b83ca383ebd2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-1900000000-c628b05706544cb1ebdc2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9300000000-bc4c631410a5cbb3c2f52017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-ccac569cbc78a632da482017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-a22c861e4f2551a3f5822017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00kf-9000000000-37421b473ba575d307fd2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0006-9200000000-1cc9b0a66b83ca383ebd2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00du-5900000000-29dc15087c785a19c0ee2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-853f5ec98c651c09e3db2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0079-1900000000-dac4165382f541a26a032017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0076-8900000000-6da8eb6b76055856b7142017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9000000000-ab76de8a8f1873f63de62017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-1900000000-173e1f32b118424e132d2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000l-5900000000-b1ebc285fc95a34dc7b12017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9200000000-66f717c0018108bc77692017-07-26View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDIMIDAZOLEACRYLIC-ACID
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).