NP-MRD: Showing NP-Card for Urocanic acid (NP0000209)

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Record Information

Version

1.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2021-08-10 02:54:38 UTC

NP-MRD ID

NP0000209

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Urocanic acid

Description

Urocanic acid 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 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.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652306242117433D          

 16 16  0  0  0  0            999 V2000
    3.2505   -1.0815   -0.3880 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7727    0.0730   -0.4068 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5877    1.1737   -0.5855 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3478    0.2927   -0.2417 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4821   -0.6996   -0.0640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9479   -0.4659    0.1008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8906   -1.4487    0.2876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1026   -0.8363    0.3988 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9294    0.4929    0.2857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5936    0.6998    0.1025 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6766    1.8223    0.1758 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9207    1.2836   -0.2556 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8987   -1.6962   -0.0484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7084   -2.5148    0.3377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6667    1.2859    0.3245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0976    1.6192   -0.0234 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10  6  1  0  0  0  0
  3 11  1  0  0  0  0
  4 12  1  0  0  0  0
  5 13  1  0  0  0  0
  7 14  1  0  0  0  0
  9 15  1  0  0  0  0
 10 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000209

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C(\[H])=C(/[H])C1=C([H])N=C([H])N1[H]

> <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_KEY>
LOIYMIARKYCTBW-OWOJBTEDSA-N

> <FORMULA>
C6H6N2O2

> <MOLECULAR_WEIGHT>
138.124

> <EXACT_MASS>
138.042927446

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
13.09524481706865

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-3-(1H-imidazol-4-yl)prop-2-enoic acid

> <ALOGPS_LOGP>
0.00

> <JCHEM_LOGP>
-1.0052561452921183

> <ALOGPS_LOGS>
-0.82

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.886392712824712

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.8470756665411976

> <JCHEM_PKA_STRONGEST_BASIC>
6.13318975489442

> <JCHEM_POLAR_SURFACE_AREA>
65.97999999999999

> <JCHEM_REFRACTIVITY>
35.5676

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.10e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
trans-urocanic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  O   UNK     0       3.251  -1.081  -0.388  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.773   0.073  -0.407  0.00  0.00           C+0
HETATM    3  O   UNK     0       3.588   1.174  -0.586  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.348   0.293  -0.242  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.482  -0.700  -0.064  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.948  -0.466   0.101  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.891  -1.449   0.288  0.00  0.00           C+0
HETATM    8  N   UNK     0      -3.103  -0.836   0.399  0.00  0.00           N+0
HETATM    9  C   UNK     0      -2.929   0.493   0.286  0.00  0.00           C+0
HETATM   10  N   UNK     0      -1.594   0.700   0.103  0.00  0.00           N+0
HETATM   11  H   UNK     0       3.677   1.822   0.176  0.00  0.00           H+0
HETATM   12  H   UNK     0       0.921   1.284  -0.256  0.00  0.00           H+0
HETATM   13  H   UNK     0       0.899  -1.696  -0.048  0.00  0.00           H+0
HETATM   14  H   UNK     0      -1.708  -2.515   0.338  0.00  0.00           H+0
HETATM   15  H   UNK     0      -3.667   1.286   0.325  0.00  0.00           H+0
HETATM   16  H   UNK     0      -1.098   1.619  -0.023  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2   11                                                       
CONECT    4    2    5   12                                                  
CONECT    5    4    6   13                                                  
CONECT    6    5    7   10                                                  
CONECT    7    6    8   14                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   15                                                  
CONECT   10    9    6   16                                                  
CONECT   11    3                                                            
CONECT   12    4                                                            
CONECT   13    5                                                            
CONECT   14    7                                                            
CONECT   15    9                                                            
CONECT   16   10                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

View in JSmol

Synonyms

Value	Source
(2E)-3-(1H-Imidazol-4-yl)acrylic acid	ChEBI
(e)-3-(1H-Imidazol-4-yl)-2-propenoic acid	ChEBI
(2E)-3-(1H-Imidazol-4-yl)acrylate	Generator
(e)-3-(1H-Imidazol-4-yl)-2-propenoate	Generator
Urocanate	Generator
3-(1H-Imidazol-4-yl)-2-propenoate	HMDB
3-(1H-Imidazol-4-yl)-2-propenoic acid	HMDB
3-(1H-Imidazol-4-yl)acrylate	HMDB
3-(1H-Imidazol-4-yl)acrylic acid	HMDB
3-(4-Imidazolyl)acrylate	HMDB
3-(4-Imidazolyl)acrylic acid	HMDB
5-Imidazoleacrylate	HMDB
5-Imidazoleacrylic acid	HMDB
Imidazole-4-acrylate	HMDB
Imidazole-4-acrylic acid	HMDB
Imidazoleacrylic acid	HMDB
Acid, glyoxalinylacrylic	HMDB
Acid, urocanic	HMDB
Glyoxalinylacrylic acid	HMDB
(2E)-3-(1H-Imidazol-5-yl)-2-propenoic acid	HMDB
(e)-3-(4-Imidazolyl)acrylic acid	HMDB
(e)-3-(Imidazol-4-yl)-2-propenoic acid	HMDB
(e)-Urocanic acid	HMDB
trans-Urocanic acid	HMDB

Chemical Formula

C₆H₆N₂O₂

Average Mass

138.1240 Da

Monoisotopic Mass

138.04293 Da

IUPAC Name

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

Traditional Name

trans-urocanic acid

CAS Registry Number

104-98-3

SMILES

[H]OC(=O)C(\[H])=C(/[H])C1=C([H])N=C([H])N1[H]

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 Key

LOIYMIARKYCTBW-OWOJBTEDSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Clostridium tetranomorphum	-	KNApSAcK
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Coprinopsis atramentaria	LOTUS Database	35616633
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Hippospongia communis	LOTUS Database	35616633
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB
Vigna radiata	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

Species Where Detected

Species Name	Source	Reference
Saccharomyces cerevisiae	KNApSAcK Database	22123792

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

urocanic acid (CHEBI:30817 )

Physical Properties

State

Solid

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 g/L	ALOGPS
logP	0	ALOGPS
logP	-1	ChemAxon
logS	-0.82	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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0000301

DrugBank ID

DB01971

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

30817

Good Scents ID

Not Available

References

General 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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:6628454 ]
Morrison H: Photochemistry and photobiology of urocanic acid. Photodermatol. 1985 Jun;2(3):158-65. [PubMed:3895185 ]

Showing NP-Card for Urocanic acid (NP0000209)

MOL for NP0000209 (Urocanic acid)

3D MOL for NP0000209 (Urocanic acid)

3D SDF for NP0000209 (Urocanic acid)

3D-SDF for NP0000209 (Urocanic acid)

PDB for NP0000209 (Urocanic acid)

3D PDB for NP0000209 (Urocanic acid)

SMILES for NP0000209 (Urocanic acid)

INCHI for NP0000209 (Urocanic acid)

Structure for NP0000209 (Urocanic acid)

3D Structure for NP0000209 (Urocanic acid)