Urocanic acid

Details

• Internal ID: 68573e04-6f51-4f73-9383-517b76e85355
• Taxonomy: Organoheterocyclic compounds > Azoles > Imidazoles > Substituted imidazoles > Imidazolyl carboxylic acids and derivatives
• IUPAC Name: (E)-3-(1H-imidazol-5-yl)prop-2-enoic acid
• SMILES (Canonical): C1=C(NC=N1)C=CC(=O)O
• SMILES (Isomeric): C1=C(NC=N1)/C=C/C(=O)O
• InChI: 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
• Popularity: 1,390 references in papers

Physical and Chemical Properties

• Molecular Formula: C₆H₆N₂O₂
• Molecular Weight: 138.12 g/mol
• Exact Mass: 138.042927438 g/mol
• Topological Polar Surface Area (TPSA): 66.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): 0.51
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• 104-98-3
• Urocaninic acid
• 3-(1H-Imidazol-4-yl)-2-propenoic acid
• (2E)-3-(1H-imidazol-4-yl)prop-2-enoic acid
• 2-Propenoic acid, 3-(1H-imidazol-4-yl)-
• G8D26XJJ3B
• NSC-66357
• 2-Propenoic acid, 3-(1H-imidazol-4-yl)-, (E)-
• CHEBI:27248
• DTXSID50859181
• Acid, Urocanic
• Glyoxalinylacrylic Acid
• Acid, Glyoxalinylacrylic
• 3-(1H-imidazol-5-yl)prop-2-enoic acid
• RefChem:901492
• DTXCID10809662
• 203-258-4
• 4-imidazoleacrylic acid
• trans-Urocanic acid
• 3465-72-3
• urocanate
• (E)-3-(1H-imidazol-5-yl)acrylic acid
• imidazoleacrylic acid
• 5-Imidazoleacrylic acid
• (2E)-3-(1H-IMIDAZOL-4-YL)ACRYLIC ACID
• (E)-3-(4-Imidazolyl)acrylic acid
• 3-Imidazol-4-ylacrylic acid
• 3-(4-Imidazolyl)acrylic acid
• MFCD00005203
• 3-(1H-imidazol-4-yl)acrylic acid
• Imidazole-4-acrylic acid
• (E)-3-(1H-imidazol-5-yl)prop-2-enoic acid
• (E)-Urocanic acid
• (E)-3-(1H-Imidazol-4-yl)-2-propenoic acid
• 4-IMIDAZOLE ACRYLIC ACID DIHYDRATE
• 2-Propenoic acid, 3-(1H-imidazol-4-yl)-, (2E)-
• MFCD01593677
• MLS000069482
• DTXSID5041148
• SMR000059098
• NSC 66357
• (2E)-3-imidazol-4-ylprop-2-enoic acid
• (E)-3-(imidazol-4-yl)propenoate
• (Z)-3-(3H-imidazol-4-yl)prop-2-enoic Acid
• (Z)-Urocanic acid;cis-UCA
• UNII-G8D26XJJ3B
• (2E)-3-(1H-Imidazole-4-yl)propenoic acid
• 3-(1H-Imidazol-5-yl)-2-propenoic acid; 4-Imidazoleacrylic acid; 5-Imidazoleacrylic acid; Urocaninic acid
• 5-Imidazoleacrylate
• Imidazole-4-acrylate
• 2-Propenoic acid, 3-(1H-imidazol-5-yl)-
• (E)-3-(1H-Imidazol-5-yl)-2-propenoic acid
• Opera_ID_26
• 3-(1H-imidazol-4-yl)prop-2-enoic acid
• UROCANIC ACID, CIS
• 3-(4-Imidazolyl)acrylate
• bmse000279
• Lopac0_001255
• SCHEMBL15417
• trans-4-imidazoleacrylic acid
• MLS001148240
• SCHEMBL338885
• UROCANIC ACID, TRANS-
• 4-Imidazoleacrylic acid, 99%
• orb1302586
• orb1692800
• 3-(1H-Imidazol-4-yl)acrylate
• CHEMBL1236602
• DTXCID3021148
• CHEBI:30817
• E-3-(4-imidazolyl)propenoic acid
• HMS2234N08
• HMS3263L12
• ALBB-025618
• NSC66357
• (E)-3-(5-Imidazolyl)acrylic Acid
• Tox21_202978
• Tox21_501255
• BBL027507
• MSK171303
• NSC407934
• s9449
• SBB006702
• STK735136
• (E)-3-(imidazol-4-yl)acrylic acid
• 3-(3H-Imidazol-4-yl)-acrylic acid
• 3-(1H-Imidazol-4-yl)-2-propenoate
• AKOS001745677
• AKOS005265082
• AKOS022488522
• (e)-3-(Imidazol-4-yl)propenoic acid
• CCG-205329
• DB01971
• FU29984
• HS-0075
• LP01255
• MSK001793-100W
• SDCCGSBI-0051222.P002
• (E)-3-(1H-imidazol-5-yl)acrylicacid
• IMIDAZOLE-4-ACRYLIC ACID, (E)-
• MSK001793-1000W
• NCGC00094495-01
• NCGC00094495-02
• NCGC00094495-03
• NCGC00094495-05
• NCGC00260524-01
• NCGC00261940-01
• CAS-104-98-3
• ST085933
• SY106830
• SY234874
• DB-222681
• HY-113008
• Urocanic acid Solution in Water, 100ug/mL
• CS-0059340
• EU-0101255
• I0002
• NS00014985
• 1H-ImidaZole-4-acrylic acid (Urocanic acid)
• 2-Propenoic acid, 3-(1H-imidazole-4-yl)-
• Urocanic acid Solution in Water, 1000ug/mL
• (E)-3-(1H-imidazol-4-yl)prop-2-enoic acid
• A11380
• C00785
• E72446
• EN300-343465
• Q30536
• U 7500
• (2E)-3-(1H-imidazol-5-yl)prop-2-enoic acid
• (E)-3-(IMIDAZOL-4-YL)-2-PROPENOIC ACID
• F795068
• Imidazole-4-propene-2-enoic acid [Urocanic acid]
• SR-01000076189
• SR-01000076189-1
• BRD-K52670952-003-01-4
• Q60998685
• 23A7DA77-EC02-46B9-AA22-514C2B2A62E9

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9960	99.60%
Caco-2	+	0.8499	84.99%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.4171	41.71%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9239	92.39%
OATP1B3 inhibitior	+	0.9508	95.08%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.9299	92.99%
P-glycoprotein inhibitior	-	0.9924	99.24%
P-glycoprotein substrate	-	0.9698	96.98%
CYP3A4 substrate	-	0.7447	74.47%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9032	90.32%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.9103	91.03%
CYP2C19 inhibition	-	0.9165	91.65%
CYP2D6 inhibition	-	0.9276	92.76%
CYP1A2 inhibition	-	0.9046	90.46%
CYP2C8 inhibition	-	0.8047	80.47%
CYP inhibitory promiscuity	-	0.9566	95.66%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8228	82.28%
Carcinogenicity (trinary)	Non-required	0.5870	58.70%
Eye corrosion	-	0.7433	74.33%
Eye irritation	+	0.9931	99.31%
Skin irritation	+	0.7501	75.01%
Skin corrosion	-	0.6454	64.54%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8492	84.92%
Micronuclear	+	0.7500	75.00%
Hepatotoxicity	+	0.5125	51.25%
skin sensitisation	-	0.9204	92.04%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	-	0.7125	71.25%
Nephrotoxicity	-	0.6830	68.30%
Acute Oral Toxicity (c)	III	0.4715	47.15%
Estrogen receptor binding	-	0.8523	85.23%
Androgen receptor binding	-	0.8513	85.13%
Thyroid receptor binding	-	0.8307	83.07%
Glucocorticoid receptor binding	-	0.8318	83.18%
Aromatase binding	-	0.7352	73.52%
PPAR gamma	-	0.6924	69.24%
Honey bee toxicity	-	0.8988	89.88%
Biodegradation	-	0.5500	55.00%
Crustacea aquatic toxicity	-	0.7900	79.00%
Fish aquatic toxicity	-	0.7176	71.76%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293237	P54132	Bloom syndrome protein	7.9 nM; 7.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	10000 nM	Potency	via CMAUP
CHEMBL5162	Q6W5P4	Neuropeptide S receptor	5011.9 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL221	P23219	Cyclooxygenase-1	84.48%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.95%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.78%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.37%	94.45%

Plants that contains it

• Astragalus oxyphysus
• Centaurea glastifolia
• Cuscuta reflexa
• Euphorbia marschalliana subsp. armena
• Galanthus nivalis
• Grindelia havardii
• Plantago depressa
• Polyscias scutellaria
• Prunus amygdalus
• Pyrus communis subsp. communis
• Senecio candollei

Cross-Links

• PubChem: 736715
• NPASS: NPC243319
• ChEMBL: CHEMBL1236602
• LOTUS: LTS0000414
• wikiData: Q60998685