P. aeruginosa Metabolome Database: urocanate (PAMDB110182)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 12:54:54 PM

Metabolite ID

PAMDB110182

Identification

Name:

urocanate

Description:

A urocanate obtained by deprotonation of the carboxy group of trans-urocanic acid; major species at pH 7.3.

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

urocanic acid
trans-urocanate

Chemical Formula:

C₆H₅N₂O₂

Average Molecular Weight:

137.12

Monoisotopic Molecular Weight:

138.0429274472

InChI Key:

LOIYMIARKYCTBW-OWOJBTEDSA-M

InChI:

InChI=1S/C6H6N2O2/c9-6(10)2-1-5-3-7-4-8-5/h1-4H,(H,7,8)(H,9,10)/p-1/b2-1+

CAS number:

104-98-3

IUPAC Name:

(2E)-3-(1H-imidazol-4-yl)prop-2-enoate

Traditional IUPAC Name:

trans-urocanic acid

SMILES:

C1(NC=NC=1C=CC([O-])=O)

Chemical Taxonomy

Taxonomy Description

This compound 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

urocanic acid (CHEBI:30817 )

Physical Properties

State:

Solid

Charge:

-1

Melting point:

225 °C

Experimental Properties:

Property	Value	Reference
Melting Point	225 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1.5 mg/mL at 17 °C	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	42.5 mg/mL	ALOGPS
logP	0.22	ALOGPS
logP	-1	ChemAxon
logS	-0.51	ALOGPS
pKa (Strongest Acidic)	3.85	ChemAxon
pKa (Strongest Basic)	6.13	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	65.98 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	35.57 m³·mol^-1	ChemAxon
Polarizability	13.1 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Not Available

Reactions:

Pathways:

Ammonia Recycling pae00910
Histidine Metabolism pae00340

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-014m-1930000000-25b091170cc3ea73bcf7	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)	splash10-00l5-1930000000-5c3c875338a517d52729	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-00di-9410000000-b58e1b2cdd5c12a6ba24	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-0159-3950000000-433e50271e182f8408fd	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00di-3900000000-8c1c060d06c1ce3fb5f7	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00kf-9000000000-ae9de21d4642045fb96c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-014l-9000000000-8e6978d7f104386d2e82	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive	splash10-000f-9200000000-cb7f9025a0f6adf740c1	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-000i-1900000000-c628b05706544cb1ebdc	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0006-9300000000-bc4c631410a5cbb3c2f5	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0006-9000000000-ccac569cbc78a632da48	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0006-9000000000-a22c861e4f2551a3f582	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-00kf-9000000000-37421b473ba575d307fd	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-00du-5900000000-29dc15087c785a19c0ee	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0006-9200000000-1cc9b0a66b83ca383ebd	View in MoNA
1D NMR	1H NMR Spectrum	Not Available
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available

References

References:

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. [16409897 ]
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. [9757593 ]
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. [9155258 ]
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. [6501514 ]
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. [11129077 ]
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. [14518047 ]
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. [6628454 ]
Morrison H: Photochemistry and photobiology of urocanic acid. Photodermatol. 1985 Jun;2(3):158-65. [3895185 ]

Synthesis Reference:

Yamamoto, 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)

Links

External Links:

Resource	Link
CAS	104-98-3
ChEBI	17771
ChemSpider	4573734
HMDB	HMDB00301
KEGG	C00785
MetaboLights	MTBLC17771
PubChem	5460052

urocanate (PAMDB110182)

Structure for urocanate (PAMDB110182)