化合物信息

ID:151

基本信息

化学结构

分子式

C₁₉H₁₂O₆

分子量

336.29498

精确质量

336.0633881

电荷

InChI

InChI=1S/C19H12O6/c20-16-10-5-1-3-7-14(10)24-18(22)12(16)9-13-17(21)11-6-2-4-8-15(11)25-19(13)23/h1-8,22-23H,9H2

InChIKey

KSKRYQVHJQRUNC-UHFFFAOYSA-N

Canonic Smiles

Oc1oc2ccccc2c(=O)c1Cc1c(O)oc2c(c1=O)cccc2

Isomeric Smiles

o1c(O)c(Cc2c(=O)c3c(oc2O)cccc3)c(=O)c2c1cccc2

计算属性

JChem

Acid pKa

-17.33553

质子受体

质子供体

LogD (pH = 5.5)

-0.050125293

LogD (pH = 7.4)

-0.050130893

Log P

-0.19872934

摩尔折射率

107.4442

极化性

33.5989

极化表面积

93.06

可自由旋转的化学键

里宾斯基五规则

true

ALOGPS 2.1

Log P

2.06

LOG S

-3.72

溶解度

6.39e-02 g/l

数据来源

学术数据

数据来源

名称和标识

别名

DicumarolDicoumarinBis-HydroxycoumarinBHCDicoumarolBishydroxycoumarin

IUPAC标准名

2-hydroxy-3-[(2-hydroxy-4-oxo-4H-chromen-3-yl)methyl]-4H-chromen-4-one

商标名

MelitoxinDicoumalDikumarolCumaDicumarineTemparinCumidAntitrombosinTrombosanDicumanKumoranDicumaol RBaracouminAcavylAcadylDufaloneDicumol

IUPAC传统名

dicumarol

名称和标识

数据登录号

PubChem SID

160963614

PubChem CID

54676038

CAS号

66-76-2

数据登录号

化合物性质

理化性质

溶解度

128 mg/L

疏水性(logP)

3.1

化合物性质

分子相关蛋白质

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分子图谱

暂无数据

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描述信息

DrugBank

DB00266

Drug Groups

approved

Description

An oral anticoagulant that interferes with the metabolism of vitamin K. It is also used in biochemical experiments as an inhibitor of reductases. [PubChem]

Indication

For decreasing blood clotting. Often used along with heparin for treatment of deep vein thrombosis.

Pharmacology

Dicumarol is an coumarin-like compound found in sweet clover. It is used as an oral anticoagulant and acts by inhibiting the hepatic synthesis of vitamin K-dependent coagulation factors (prothrombin and factors VII, IX, and X). It is also used in biochemical experiments as an inhibitor of reductases.

Toxicity

LD₅₀=233 mg/kg (orally in mice); LD₅₀=250 mg/kg (orally in rats)

Affected Organisms

Humans and other mammals

References

• Cullen JJ, Hinkhouse MM, Grady M, Gaut AW, Liu J, Zhang YP, Weydert CJ, Domann FE, Oberley LW: Dicumarol inhibition of NADPH:quinone oxidoreductase induces growth inhibition of pancreatic cancer via a superoxide-mediated mechanism. Cancer Res. 2003 Sep 1;63(17):5513-20. [Pubmed]

• Mironov AA, Colanzi A, Polishchuk RS, Beznoussenko GV, Mironov AA Jr, Fusella A, Di Tullio G, Silletta MG, Corda D, De Matteis MA, Luini A: Dicumarol, an inhibitor of ADP-ribosylation of CtBP3/BARS, fragments golgi non-compact tubular zones and inhibits intra-golgi transport. Eur J Cell Biol. 2004 Jul;83(6):263-79. [Pubmed]

• Abdelmohsen K, Stuhlmann D, Daubrawa F, Klotz LO: Dicumarol is a potent reversible inhibitor of gap junctional intercellular communication. Arch Biochem Biophys. 2005 Feb 15;434(2):241-7. [Pubmed]

• Thanos CG, Liu Z, Reineke J, Edwards E, Mathiowitz E: Improving relative bioavailability of dicumarol by reducing particle size and adding the adhesive poly(fumaric-co-sebacic) anhydride. Pharm Res. 2003 Jul;20(7):1093-100. [Pubmed]

External Links

• [Wikipedia]

描述信息

参考文献

PubChem文献

数据源提供

• Abdelmohsen K, Stuhlmann D, Daubrawa F, Klotz LO: Dicumarol is a potent reversible inhibitor of gap junctional intercellular communication. Arch Biochem Biophys. 2005 Feb 15;434(2):241-7. Pubmed

参考文献

生物活性

PubChem BioAssay

生物活性

导航

基本信息

计算属性

• RDKit

• JChem

• ALOGPS 2.1

数据来源

• 学术数据

名称和标识

• 别名

• IUPAC标准名

• 商标名

• IUPAC传统名

数据登录号

• PubChem SID

• PubChem CID

• CAS号

• 理化性质

• DrugBank

• PubChem文献

• 数据源提供

生物活性

• PubChem BioAssay

别名

DicumarolDicoumarinBis-HydroxycoumarinBHCDicoumarolBishydroxycoumarin

IUPAC标准名

2-hydroxy-3-[(2-hydroxy-4-oxo-4H-chromen-3-yl)methyl]-4H-chromen-4-one

商标名

MelitoxinDicoumalDikumarolCumaDicumarineTemparinCumidAntitrombosinTrombosanDicumanKumoranDicumaol RBaracouminAcavylAcadylDufaloneDicumol

IUPAC传统名

dicumarol

PubChem SID

160963614

PubChem CID

54676038

理化性质

溶解度

128 mg/L

疏水性(logP)

3.1

DrugBank

DB00266

Drug Groups

approved

Description

An oral anticoagulant that interferes with the metabolism of vitamin K. It is also used in biochemical experiments as an inhibitor of reductases. [PubChem]

Indication

For decreasing blood clotting. Often used along with heparin for treatment of deep vein thrombosis.

Pharmacology

Toxicity

LD₅₀=233 mg/kg (orally in mice); LD₅₀=250 mg/kg (orally in rats)

Affected Organisms

Humans and other mammals

References

External Links

• [Wikipedia]

数据源提供

• Abdelmohsen K, Stuhlmann D, Daubrawa F, Klotz LO: Dicumarol is a potent reversible inhibitor of gap junctional intercellular communication. Arch Biochem Biophys. 2005 Feb 15;434(2):241-7. Pubmed