CAS 104-98-3|CAS 7699-35-6|CAS 3465-72-3|trans-urocanic acid|(2E)-3-(1H-imidazol-4-yl)prop-2-enoic acid|(2e)-3-(1h-Imidazol-4-Yl)Acrylic Acid|(2E)-3-(3H-imidazol-4-yl)prop-2-enoic acid|(E)-3-(1H-Imi...

基本信息

化学结构

分子式

C₆H₆N₂O₂

分子量

138.12404

精确质量

138.04292744

电荷

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+

InChIKey

LOIYMIARKYCTBW-OWOJBTEDSA-N

Canonic Smiles

OC(=O)/C=C/c1c[nH]cn1

Isomeric Smiles

OC(=O)/C=C/c1c[nH]cn1

计算属性

JChem

LogD (pH = 7.4)

-2.25

LogD (pH = 5.5)

-1.08

Log P

-1.02

可自由旋转的化学键

质子供体

质子受体

里宾斯基五规则

true

Acid pKa

3.76

极化表面积

65.98

极化性

13.10

摩尔折射率

35.57

LOG S

-1.14

数据来源

名称和标识

IUPAC传统名

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

IUPAC标准名

(2E)-3-(1H-imidazol-4-yl)prop-2-enoic acid (2E)-3-(1H-imidazol-5-yl)prop-2-enoic acid 3-(1H-imidazol-4-yl)prop-2-enoic acid 3-(1H-imidazol-5-yl)prop-2-enoic acid

别名

(2e)-3-(1h-Imidazol-4-Yl)Acrylic Acid(E)-3-(1H-Imidazol-5-yl)-2-propenoic acidUROCANIC ACID4-咪唑丙烯酸3-(1H-imidazol-4-yl)acrylic acid尿刊酸3-(4-咪唑基)丙烯酸4-Imidazoleacrylic acid4-Imidazoleacrylic acid3-(4-Imidazolyl)acrylic acidUrocanic acid(E)-3-(1H-imidazol-4-yl)acrylic acidcis-Urocanic acidcis-3-(1H-imidazol-4-yl)-2-propenoic acidcis-UCA3-(1 H -Imidazol-4-yl)-2-propenoic acid; 4-Imidazoleacrylic acidUrocaninic acidUrocanic acidtrans-urocanic acid(2E)-3-(1H-imidazol-4-yl)acrylic acidtrans-urocanic acid(E)-3-(1H-imidazol-4-yl)-2-propenoic acidUrocanic acid3-(1H-imidazol-4-yl)-2-propenoic acidurocanic acid3-imidazol-4-ylacrylic acid

名称和标识

数据登录号

Beilstein号

81405814038128219

EC号

203-258-4

MDL号

MFCD00005203MFCD01593677MFCD11045310

CAS号

104-98-37699-35-63465-72-3

维基百科标题

数据登录号

化合物性质

理化性质

药理学性质

Gabaminergic

化合物性质

分子相关蛋白质

分子图谱

暂无数据

点击上传数据

描述信息

DrugBank

DB01971

Drug information: experimental

MP Biomedicals

02103221

Crystalline

05206291

MP Biomedicals Rare Chemical collection

Wikipedia

Urocanic_acid

Sigma Aldrich

859796

包装
25, 100 g in poly bottle
5 g in glass bottle

U6883

Biochem/physiol Actions
cis-Urocanic acid, a 5-HT agonist, is a product of uv isomerization of trans-urocanic acid in skin, which leads to immunosuppression via activation of 5-HT2A receptor.

ChEBI

CHEBI:30817

A urocanic acid in which the double bond of the carboxyethene moiety has E configuration.

CHEBI:27248

An alpha,beta-unsaturated monocarboxylic acid that is prop-2-enoic acid substituted by a 1H-imidazol-4-yl group at position 3. It is a metabolite of hidtidine.

描述信息

参考文献

PubChem文献

数据源提供

• List, F.H. et al., Hoppe Seyler's Z. Physiol. Chem., 1960, 319, 17, (isol)

• Baden, H. et al., Nature (London), 1966, 210, 732, (pmr)

• Svinning, T., Acta Cryst. B, 1979, 35, 2813, (cryst struct)

• Hanson, K.M. et al., J.A.C.S., 1997, 119, 2715, (spectra)

• Biochem. Prep., 1955, 4, 50, (synth)

• Gregoire, J. et al., Bull. Soc. Chim. Belg., 1958, 40, 767, (isol)

• Shibatari, T. et al., Appl. Microbiol., 1974, 27, 688, (biosynth)

• Aldrich Library of NMR Spectra, 2nd edn., 1983, 2, 492A, (nmr)

• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 621A, (ir)

• Edlbacher, S. et al., Hoppe Seyler's Z. Physiol. Chem., 1942, 276, 126; 1943, 279, 63, (isol, biosynth)

• Japan. Pat., 1961, 61 23 094; CA, 60, 2302, (isol)

• Ienaga, K. et al., J. Het. Chem., 1988, 25, 1037, (deriv)

参考文献

生物活性

PubChem BioAssay

生物活性

名称和标识

IUPAC传统名

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

IUPAC标准名

(2E)-3-(1H-imidazol-4-yl)prop-2-enoic acid (2E)-3-(1H-imidazol-5-yl)prop-2-enoic acid 3-(1H-imidazol-4-yl)prop-2-enoic acid 3-(1H-imidazol-5-yl)prop-2-enoic acid

别名

描述信息

DrugBank

DB01971

Drug information: experimental

MP Biomedicals

02103221

Crystalline

05206291

MP Biomedicals Rare Chemical collection

Wikipedia

Urocanic_acid

Sigma Aldrich

859796

包装
25, 100 g in poly bottle
5 g in glass bottle

U6883

Biochem/physiol Actions
cis-Urocanic acid, a 5-HT agonist, is a product of uv isomerization of trans-urocanic acid in skin, which leads to immunosuppression via activation of 5-HT2A receptor.

ChEBI

CHEBI:30817

A urocanic acid in which the double bond of the carboxyethene moiety has E configuration.

CHEBI:27248

An alpha,beta-unsaturated monocarboxylic acid that is prop-2-enoic acid substituted by a 1H-imidazol-4-yl group at position 3. It is a metabolite of hidtidine.

参考文献

PubChem文献

数据源提供

• List, F.H. et al., Hoppe Seyler's Z. Physiol. Chem., 1960, 319, 17, (isol)

• Baden, H. et al., Nature (London), 1966, 210, 732, (pmr)

• Svinning, T., Acta Cryst. B, 1979, 35, 2813, (cryst struct)

• Hanson, K.M. et al., J.A.C.S., 1997, 119, 2715, (spectra)

• Biochem. Prep., 1955, 4, 50, (synth)

• Gregoire, J. et al., Bull. Soc. Chim. Belg., 1958, 40, 767, (isol)

• Shibatari, T. et al., Appl. Microbiol., 1974, 27, 688, (biosynth)

• Aldrich Library of NMR Spectra, 2nd edn., 1983, 2, 492A, (nmr)

• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 621A, (ir)

• Edlbacher, S. et al., Hoppe Seyler's Z. Physiol. Chem., 1942, 276, 126; 1943, 279, 63, (isol, biosynth)

• Japan. Pat., 1961, 61 23 094; CA, 60, 2302, (isol)

• Ienaga, K. et al., J. Het. Chem., 1988, 25, 1037, (deriv)

生物活性

PubChem BioAssay

数据登录号

Beilstein号

81405814038128219

EC号

203-258-4

MDL号

MFCD00005203MFCD01593677MFCD11045310

CAS号

104-98-37699-35-63465-72-3

维基百科标题

化合物性质

理化性质

药理学性质

Gabaminergic

化合物信息

ID:1738