Toddalolactone - 10mM in DMSO , CAS No.483-90-9

CAS: 483-90-9 Cat. No.: T424199 Molecular Weight: 308.33 PubChem CID: 160485

GRADE & PURITY 10mM in DMSO

Synonyms

2H-1-Benzopyran-2-one, 6-(2,3-dihydroxy-3-methylbutyl)-5,7-dimethoxy- | 6-[(2R)-2,3-dihydroxy-3-methylbutyl]-5,7-dimethoxychromen-2-one | CCG-267560 | Toddalolactone | (+)-Toddalolactone | MS-24465 | AC-34493 | s9194 | DTXSID00197484 | AKOS000277888 | HY-

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

Information

Toddalolactone Toddalolactone, a natural coumarin, inhibits the activity of recombinant human Plasminogen activator inhibitor-1 (PAI-1) in a dose-dependent manner, yielding an IC50 value of 37.31 ± 3.23 μM.

Targets

PAI-1 37.31 μM

In vitro

Toddalolactone inhibits the binding between PAI-1 and uPA, and therefore prevented the formation of the PAI-1/uPA complex.

In vivo

Intraperitoneal injection of toddalolactone in mice significantly prolonged tail bleeding and reduced arterial thrombus weight in a FeCl3-induced thrombosis model. Moreover, the hydroxyproline level in the plasma and the degree of liver fibrosis in mice were decreased after intraperitoneal injection of toddalolactone in CCl4-induced mouse liver fibrosis model.

Specifications

Synonyms

2H-1-Benzopyran-2-one, 6-(2, 3-dihydroxy-3-methylbutyl)-5, 7-dimethoxy- | 6-[(2R)-2, 3-dihydroxy-3-methylbutyl]-5, 7-dimethoxychromen-2-one | CCG-267560 | Toddalolactone | (+)-Toddalolactone | MS-24465 | AC-34493 | s9194 | DTXSID00197484 | AKOS000277888 | HY-

Specifications & Purity

10mM in DMSO

Biochemical and Physiological Mechanisms

Toddalolactone, a natural coumarin, inhibits the activity of recombinant human Plasminogen activator inhibitor-1 (PAI-1) in a dose-dependent manner, yielding an IC50 value of 37.31 ± 3.23 μM.

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

This product requires cold chain shipping. Ground and other economy services are not available.

Product Properties

• ALogP: 1.655
• HBD Count: 1
• Rotatable Bond: 5

Names and Identifiers

• Pubchem Sid: 528771919
• Canonical Smiles: CC(C)(C(CC1=C(C=C2C(=C1OC)C=CC(=O)O2)OC)O)O
• IUPAC Name: 6-[(2R)-2,3-dihydroxy-3-methylbutyl]-5,7-dimethoxychromen-2-one
• InChIKey: GLWPLQBQHWYKRK-CYBMUJFWSA-N
• INCHI: 1S/C16H20O6/c1-16(2,19)13(17)7-10-11(20-3)8-12-9(15(10)21-4)5-6-14(18)22-12/h5-6,8,13,17,19H,7H2,1-4H3/t13-/m1/s1
• Isomeric SMILES: CC(C)([C@@H](CC1=C(C=C2C(=C1OC)C=CC(=O)O2)OC)O)O
• PubChem CID: 160485
• Molecular Weight: 308.33

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Class Coumarins and derivatives

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Class: Coumarins and derivatives
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Coumarins and derivatives
• Alternative Parents: 1-benzopyrans Anisoles Pyranones and derivatives Alkyl aryl ethers Tertiary alcohols Heteroaromatic compounds Secondary alcohols Lactones 1,2-diols Oxacyclic compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Coumarin - Benzopyran - 1-benzopyran - Anisole - Alkyl aryl ether - Pyranone - Pyran - Benzenoid - Tertiary alcohol - Heteroaromatic compound - Secondary alcohol - 1,2-diol - Lactone - Oxacycle - Ether - Organoheterocyclic compound - Organooxygen compound - Hydrocarbon derivative - Organic oxide - Organic oxygen compound - Alcohol - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one).
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Mechanisms of Action

Chemical and Physical Properties

• DMSO(mg / mL) Max Solubility: 61
• DMSO(mM) Max Solubility: 197.842286615742
• Molecular Weight: 308.330 g/mol
• XLogP3: 1.400
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 308.126 Da
• Monoisotopic Mass: 308.126 Da
• Topological Polar Surface Area: 85.200 Ų
• Heavy Atom Count: 22
• Formal Charge: 0
• Complexity: 432.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1