CAS 63177-57-1|methyl 3-(2,5-dihydroxyphenyl)prop-2-enoate|Methyl 2,5-dihydroxycinnamate|methyl 3-(2,5-dihydroxyphenyl)prop-2-enoate|ERBSTATIN ANALOG|methyl (2E)-3-(2,5-dihydroxyphenyl)prop-2-enoate...

General Information

Structure

Molecular Formula

C₁₀H₁₀O₄

Molecular Mass

194.184

Exact Mass

194.0579088

Charge

InChI

InChI=1S/C10H10O4/c1-14-10(13)5-2-7-6-8(11)3-4-9(7)12/h2-6,11-12H,1H3

InChIKey

BQCNSTFWSKOWMA-UHFFFAOYSA-N

Canonic Smiles

COC(=O)/C=C/c1cc(O)ccc1O

Isomeric Smiles

COC(=O)/C=C/c1c(O)ccc(O)c1

Calculated Properties

JChem

Acid pKa

9.48247

H Acceptors

H Donor

LogD (pH = 5.5)

1.908138

LogD (pH = 7.4)

1.9046254

Log P

1.908183

Molar Refractivity

51.7908

Polarizability

19.525108

Polar Surface Area

66.76

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Commercial Catalog

Academic Data

Data Source

Names and Identifiers

IUPAC name

methyl 3-(2,5-dihydroxyphenyl)prop-2-enoate methyl (2E)-3-(2,5-dihydroxyphenyl)prop-2-enoate

Synonyms

Methyl 2,5-dihydroxycinnamateERBSTATIN ANALOG2,5-Dihydroxycinnamic acid methyl esterErbstatin analogMethyl 2,5-Dihydroxycinnamate3-(2,5-Dihydroxyphenyl)-2-propenoic Acid Methyl Ester

IUPAC Traditional name

methyl 3-(2,5-dihydroxyphenyl)prop-2-enoate methyl (2E)-3-(2,5-dihydroxyphenyl)prop-2-enoate

Names and Identifiers

Registration numbers

CAS Number

MDL Number

PubChem SID

PubChem CID

Registration numbers

Properties

Product Information

Certificate of Analysis

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Purity

>98%

≥95%

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

Sigma Aldrich

D2667

Biochem/physiol Actions
Inhibitor of EGF receptor-associated tyrosine kinase.
Caution
Photosensitive.
Linkage
Stable analog of erbstatin.

MP Biomedicals

02158813

Purity: >98%
Erbstatin is a novel inhibitor of the EGF receptor associated tyrosine kinase¹ . It is an unstable compound and is completely inactivated in serum in 30 minutes. Methyl 2,5-dihydroxycinnamate is a stable erbstatin analog retaining activity after a 60 minute incubation. It inhibits EGF receptor associated tyrosine kinase in vitro (IC₅₀ =0.77 μM)² . Inhibition is competitive with substrate and noncompetitive with ATP.

TRC

M302700

A stable Erbstatin analogue that inhibits tyrosine kinase. Shown to delay the S-phase induction by epidermal growth factor in quiescent normal rat kidney cells, without affecting the total amount of DNA synthesis.

Molecule Details

References

PubChem Literature

From Data Sources

• Imoto, M., et al., Biochem. Int. , 15 : 989 (1987).

• Umezawa, K., et al., FEBS Lett. , 260 : 198 (1990).

• Zheng, J., et al.: Br. J. Pharmacol., 130, 1115 (2000)

• Reznick, R., et al.: J. Physiol., 574, 33 (2000)

• Zhou, G., et al.: J. Clin. Invest., 108, 1167 (2000)

References

Bioactivity

PubChem BioAssay

Bioactivity

Data Source

Commercial Catalog

Academic Data

Names and Identifiers

IUPAC name

methyl 3-(2,5-dihydroxyphenyl)prop-2-enoate methyl (2E)-3-(2,5-dihydroxyphenyl)prop-2-enoate

Synonyms

Methyl 2,5-dihydroxycinnamateERBSTATIN ANALOG2,5-Dihydroxycinnamic acid methyl esterErbstatin analogMethyl 2,5-Dihydroxycinnamate3-(2,5-Dihydroxyphenyl)-2-propenoic Acid Methyl Ester

IUPAC Traditional name

methyl 3-(2,5-dihydroxyphenyl)prop-2-enoate methyl (2E)-3-(2,5-dihydroxyphenyl)prop-2-enoate

Registration numbers

CAS Number

MDL Number

PubChem SID

PubChem CID

Molecule Details