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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-11-09 23:13:18 UTC
HMDB IDHMDB0000301
Secondary Accession Numbers
  • HMDB0002280
  • HMDB00301
  • HMDB0034174
  • HMDB02280
  • HMDB34174
Metabolite Identification
Common NameUrocanic acid
DescriptionUrocanic acid (CAS: 104-98-3) is a breakdown (deamination) product of histidine. In the liver, urocanic acid is an intermediate in the conversion of histidine to glutamic acid, whereas, in the epidermis, it accumulates and may be both a UV protectant and an immunoregulator. Urocanic acid (UA) exists as a trans isomer (t-UA, approximately 30 mg/cm2) in the uppermost layer of the skin (stratum corneum). t-UA is formed as the cells of the second layer of the skin become metabolically inactive. During this process, proteins and membranes degrade, histidine is released, and histidase (histidine ammonia lyase) catalyzes the deamination of histidine to form t-UA. t-UA accumulates in the epidermis until removal by either the monthly skin renewal cycle or sweat. Upon absorption of UV light, the naturally occurring t-UA isomerizes to its cis form, c-UA. Because DNA lesions (e.g., pyrimidine dimers) in the lower epidermis can result from UV-B absorption, initial research proposed that t-UA acted as a natural sunscreen absorbing UV-B in the stratum corneum before the damaging rays could penetrate into lower epidermal zones. Researchers have found that c-UA also suppresses contact hypersensitivity and delayed hypersensitivity, reduces the Langerhans cell count in the epidermis, prolongs skin-graft survival time, and affects natural killer cell activity. (E)-Urocanic acid is found in mushrooms. It has been isolated from Coprinus atramentarius (common ink cap) and Phallus impudicus (common stinkhorn).
Structure
Data?1582752121
Synonyms
ValueSource
(2E)-3-(1H-Imidazol-4-yl)acrylic acidChEBI
(e)-3-(1H-Imidazol-4-yl)-2-propenoic acidChEBI
(2E)-3-(1H-Imidazol-4-yl)acrylateGenerator
(e)-3-(1H-Imidazol-4-yl)-2-propenoateGenerator
UrocanateGenerator
3-(1H-Imidazol-4-yl)-2-propenoateHMDB
3-(1H-Imidazol-4-yl)-2-propenoic acidHMDB
3-(1H-Imidazol-4-yl)acrylateHMDB
3-(1H-Imidazol-4-yl)acrylic acidHMDB
3-(4-Imidazolyl)acrylateHMDB
3-(4-Imidazolyl)acrylic acidHMDB
5-ImidazoleacrylateHMDB
5-Imidazoleacrylic acidHMDB
Imidazole-4-acrylateHMDB
Imidazole-4-acrylic acidHMDB
Imidazoleacrylic acidHMDB
Acid, glyoxalinylacrylicHMDB
Acid, urocanicHMDB
Glyoxalinylacrylic acidHMDB
(2E)-3-(1H-Imidazol-5-yl)-2-propenoic acidHMDB
(e)-3-(4-Imidazolyl)acrylic acidHMDB
(e)-3-(Imidazol-4-yl)-2-propenoic acidHMDB
(e)-Urocanic acidHMDB
trans-Urocanic acidHMDB
Chemical FormulaC6H6N2O2
Average Molecular Weight138.124
Monoisotopic Molecular Weight138.042927446
IUPAC Name(2E)-3-(1H-imidazol-4-yl)prop-2-enoic acid
Traditional Nametrans-urocanic acid
CAS Registry Number3465-72-3
SMILES
OC(=O)\C=C\C1=CNC=N1
InChI Identifier
InChI=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
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
Physiological effect

Adverse health effect

Disposition

Biological location

Source

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point225 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.5 mg/mL at 17 °CNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-MetCCS_train_neg118.77830932474
[M+H]+MetCCS_train_pos134.11130932474
[M-H]-Not Available121.6http://allccs.zhulab.cn/database/detail?ID=AllCCS00000321
[M+H]+Not Available135.5http://allccs.zhulab.cn/database/detail?ID=AllCCS00000321
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+129.63632859911
AllCCS[M-H]-125.21232859911
DeepCCS[M+H]+125.81430932474
DeepCCS[M-H]-122.38230932474
DeepCCS[M-2H]-159.62630932474
DeepCCS[M+Na]+134.88630932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Urocanic acidOC(=O)\C=C\C1=CNC=N12784.0Standard polar33892256
Urocanic acidOC(=O)\C=C\C1=CNC=N11873.8Standard non polar33892256
Urocanic acidOC(=O)\C=C\C1=CNC=N11783.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Urocanic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)/C=C/C1=C[NH]C=N11716.6Semi standard non polar33892256
Urocanic acid,1TMS,isomer #2C[Si](C)(C)N1C=NC(/C=C/C(=O)O)=C11919.6Semi standard non polar33892256
Urocanic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)/C=C/C1=CN([Si](C)(C)C)C=N11901.1Semi standard non polar33892256
Urocanic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)/C=C/C1=CN([Si](C)(C)C)C=N11901.4Standard non polar33892256
Urocanic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)/C=C/C1=CN([Si](C)(C)C)C=N12061.7Standard polar33892256
Urocanic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)/C=C/C1=C[NH]C=N11971.5Semi standard non polar33892256
Urocanic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C=NC(/C=C/C(=O)O)=C12140.8Semi standard non polar33892256
Urocanic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)/C=C/C1=CN([Si](C)(C)C(C)(C)C)C=N12384.0Semi standard non polar33892256
Urocanic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)/C=C/C1=CN([Si](C)(C)C(C)(C)C)C=N12296.4Standard non polar33892256
Urocanic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)/C=C/C1=CN([Si](C)(C)C(C)(C)C)C=N12221.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Urocanic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-014m-1930000000-25b091170cc3ea73bcf72014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Urocanic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-00l5-1930000000-5c3c875338a517d527292014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Urocanic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-00di-9410000000-b58e1b2cdd5c12a6ba242014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Urocanic acid GC-MS (2 TMS)splash10-0159-3950000000-433e50271e182f8408fd2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Urocanic acid EI-B (Non-derivatized)splash10-000f-9200000000-cb7f9025a0f6adf740c12017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Urocanic acid GC-EI-TOF (Non-derivatized)splash10-014m-1930000000-25b091170cc3ea73bcf72017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Urocanic acid GC-EI-TOF (Non-derivatized)splash10-00l5-1930000000-5c3c875338a517d527292017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Urocanic acid GC-EI-TOF (Non-derivatized)splash10-00di-9410000000-b58e1b2cdd5c12a6ba242017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Urocanic acid GC-MS (Non-derivatized)splash10-0159-3950000000-433e50271e182f8408fd2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Urocanic acid GC-EI-TOF (Non-derivatized)splash10-014m-1930000000-3815ef1f1f386e091dc32017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Urocanic acid GC-EI-TOF (Non-derivatized)splash10-00dm-2900000000-aaefc749352097679e8f2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Urocanic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-000f-9500000000-7f0462e0ef244d2118a82017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Urocanic acid GC-MS (1 TMS) - 70eV, Positivesplash10-00di-6910000000-b1e081746388d0700ce02017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Urocanic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Urocanic acid GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Urocanic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Urocanic acid GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Urocanic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-00di-3900000000-8c1c060d06c1ce3fb5f72012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Urocanic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-00kf-9000000000-ae9de21d4642045fb96c2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Urocanic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-014l-9000000000-8e6978d7f104386d2e822012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Urocanic acid EI-B (HITACHI M-80) , Positive-QTOFsplash10-000f-9200000000-cb7f9025a0f6adf740c12012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Urocanic acid LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOFsplash10-000i-1900000000-c628b05706544cb1ebdc2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Urocanic acid LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOFsplash10-0006-9300000000-bc4c631410a5cbb3c2f52012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Urocanic acid LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOFsplash10-0006-9000000000-ccac569cbc78a632da482012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Urocanic acid LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOFsplash10-0006-9000000000-a22c861e4f2551a3f5822012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Urocanic acid LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOFsplash10-00kf-9000000000-37421b473ba575d307fd2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Urocanic acid LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOFsplash10-00du-5900000000-29dc15087c785a19c0ee2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Urocanic acid LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOFsplash10-0006-9200000000-1cc9b0a66b83ca383ebd2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Urocanic acid LC-ESI-QQ , negative-QTOFsplash10-000i-1900000000-c628b05706544cb1ebdc2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Urocanic acid LC-ESI-QQ , negative-QTOFsplash10-0006-9300000000-bc4c631410a5cbb3c2f52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Urocanic acid LC-ESI-QQ , negative-QTOFsplash10-0006-9000000000-ccac569cbc78a632da482017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Urocanic acid LC-ESI-QQ , negative-QTOFsplash10-0006-9000000000-a22c861e4f2551a3f5822017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Urocanic acid LC-ESI-QQ , negative-QTOFsplash10-00kf-9000000000-37421b473ba575d307fd2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Urocanic acid LC-ESI-QTOF , negative-QTOFsplash10-0006-9200000000-1cc9b0a66b83ca383ebd2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Urocanic acid LC-ESI-QTOF , positive-QTOFsplash10-00du-5900000000-29dc15087c785a19c0ee2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Urocanic acid 20V, Negative-QTOFsplash10-0006-9000000000-853f5ec98c651c09e3db2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Urocanic acid 10V, Positive-QTOFsplash10-0079-1900000000-dac4165382f541a26a032017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Urocanic acid 20V, Positive-QTOFsplash10-0076-8900000000-6da8eb6b76055856b7142017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Urocanic acid 40V, Positive-QTOFsplash10-014i-9000000000-ab76de8a8f1873f63de62017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Urocanic acid 10V, Negative-QTOFsplash10-000i-1900000000-173e1f32b118424e132d2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Urocanic acid 20V, Negative-QTOFsplash10-000l-5900000000-b1ebc285fc95a34dc7b12017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Urocanic acid 40V, Negative-QTOFsplash10-00kf-9200000000-66f717c0018108bc77692017-07-26Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Quadrupole Ion Trap, ESI-, Adduct: [M-H]-)2022-02-11FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
  • Sweat
  • Urine
Tissue Locations
  • Epidermis
  • Liver
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.43 +/- 0.33 uMAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)FemaleNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified643 nmol/g wet fecesAdult (>18 years old)Not Specified
Normal
details
FecesDetected and Quantified660 nmol/g wet fecesAdult (>18 years old)Not Specified
Normal
details
FecesDetected and Quantified790 nmol/g wet fecesAdult (>18 years old)Not Specified
Normal
details
SalivaDetected and Quantified5.49 +/- 5.14 uMAdult (>18 years old)Male
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified5.78 +/- 13.1 uMAdult (>18 years old)Both
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified6.13 +/- 16.3 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.942 +/- 1.54 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified7.25 +/- 12.7 uMAdult (>18 years old)Both
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified1.04 +/- 2.19 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified1.23 +/- 1.70 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified1.49 +/- 1.98 uMAdult (>18 years old)Both
Normal
    • Sugimoto et al. (...
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SweatDetected and Quantified< 10 uMAdult (60 years old)Male
Normal
details
SweatDetected and Quantified< 10 uMAdult (40 years old)Male
Normal
details
SweatDetected but not QuantifiedNot QuantifiedAdult BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified<1000 umol/mmol creatinineAdolescent (13-18 years old)Not SpecifiedNormal details
UrineDetected and Quantified0.29 (0.0-0.78) umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
details
UrineDetected and Quantified0.87-1.5 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified0.68-1.2 umol/mmol creatinineAdult (>18 years old)MaleNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
UrineDetected and Quantified6.872 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
details
UrineDetected and Quantified158-202 umol/mmol creatinineAdolescent (13-18 years old)Not SpecifiedUrocanase deficiency details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. 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 ]
Eosinophilic esophagitis
  1. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Urocanase deficiency
  1. Espinos C, Pineda M, Martinez-Rubio D, Lupo V, Ormazabal A, Vilaseca MA, Spaapen LJ, Palau F, Artuch R: Mutations in the urocanase gene UROC1 are associated with urocanic aciduria. J Med Genet. 2009 Jun;46(6):407-11. doi: 10.1136/jmg.2008.060632. Epub 2009 Mar 19. [PubMed:19304569 ]
Associated OMIM IDs
DrugBank IDDB01971
Phenol Explorer Compound IDNot Available
FooDB IDFDB007506
KNApSAcK IDNot Available
Chemspider ID643824
KEGG Compound IDC00785
BioCyc IDNot Available
BiGG ID35990
Wikipedia LinkUrocanic_acid
METLIN ID298
PubChem Compound736715
PDB IDNot Available
ChEBI ID30817
Food Biomarker OntologyNot Available
VMH IDURCAN
MarkerDB IDMDB00000140
Good Scents IDNot Available
References
Synthesis ReferenceYamamoto, Kozo; Sato, Tadashi; Tosa, Tetsuya; Chibata, Ichiro. Continuous production of urocanic acid by immobilized Achromobacter liquidum cells. Biotechnology and Bioengineering (1974), 16(12), 1601-10.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Sastry CM, Whitmore SE, Breysse PN, Morison WL, Strickland PT: The effect of clinical UVA/B exposures on urinary urocanic acid isomer levels in individuals with caucasian type (II/III) skin types. Dermatol Online J. 2005 Dec 1;11(3):1. [PubMed:16409897 ]
  2. Hug DH, Hunter JK, Dunkerson DD: The potential role for urocanic acid and sunlight in the immune suppression associated with protein malnutrition. J Photochem Photobiol B. 1998 Jul 10;44(2):117-23. [PubMed:9757593 ]
  3. Snellman E, Jansen CT, Laihia JK, Milan T, Koulu L, Leszczynski K, Pasanen P: Urocanic acid concentration and photoisomerization in Caucasian skin phototypes. Photochem Photobiol. 1997 May;65(5):862-5. [PubMed:9155258 ]
  4. Schwarz W, Langer K, Haag A: High-performance liquid chromatographic determination of (Z)-and (E)-urocanic acid in human skin. J Chromatogr. 1984 Sep 14;310(1):188-92. [PubMed:6501514 ]
  5. Hermann K, Abeck D: Determination of histidine and urocanic acid isomers in the human skin by high-performance capillary electrophoresis. J Chromatogr B Biomed Sci Appl. 2000 Nov 10;749(1):41-7. [PubMed:11129077 ]
  6. Kinuta M, Kinuta K, Yamada H, Abe T, Yoshida Y, Araki K, Li SA, Otsuka A, Nakanishi A, Moriyama Y, Takei K: Formation of S-[2-carboxy-1-(1H-imidazol-4-yl) ethyl]glutathione, a new metabolite of L-histidine, from cis-urocanic acid and glutathione by the action of glutathione S-transferase. Electrophoresis. 2003 Sep;24(18):3212-8. [PubMed:14518047 ]
  7. Yokoya S, Tokuhiro E, Suwa S, Maesaka H: Measurement of the skin urocanic acid content in normal and histidinemic infants. Eur J Pediatr. 1983 Sep;140(4):330-2. [PubMed:6628454 ]
  8. Morrison H: Photochemistry and photobiology of urocanic acid. Photodermatol. 1985 Jun;2(3):158-65. [PubMed:3895185 ]
  9. Oesterwitz H, Gruner S, Diezel W, Schneider W: Inhibition of rat heart allograft rejection by a PUVA treatment of the graft recipient. Role of cisurocanic acid. Transpl Int. 1990 May;3(1):8-11. [PubMed:2369484 ]
  10. 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 ]
  11. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

General function:
Involved in histidine ammonia-lyase activity
Specific function:
Not Available
Gene Name:
HAL
Uniprot ID:
P42357
Molecular weight:
49122.09
Reactions
L-Histidine → Urocanic acid + Ammoniadetails
General function:
Involved in urocanate hydratase activity
Specific function:
Not Available
Gene Name:
UROC1
Uniprot ID:
Q96N76
Molecular weight:
80911.275
Reactions
4-Imidazolone-5-propionic acid → Urocanic acid + Waterdetails