Salviolone , CAS No.119400-86-1

CAS: 119400-86-1 Cat. No.: S651322 Molecular Weight: 268.35 PubChem CID: 10355691

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Overview

Salviolone is a natural diterpenoid derivative that can against melanoma cells. Salviolone exhibits a pleiotropic effect against melanoma by hampering cell cycle progression, STAT3 signaling, and malignant phenotype of A375 melanoma cells.

In Vitro

Salviolone (5-60 μM; 72 hours) reduces cell viability in the A375 and MeWo melanoma cell lines with EC 50 values of 17 µM and 22 µM, respectively. Salviolone does not affect the growth of normal melanocytes. Salviolone (20 μM; 48-72 hours) strongly reduces pRb, pCdk2, and cyclin A2, Tyr705-STAT3 phosphorylation expression levels in A375 cells. Salviolone also strongly increases the P21 and P53 protein expression level. Salviolone induces sustained activation of the phosphorylation of ERK1/2 and Akt. Salviolone (10-20 μM) inhibits MMP2 gelatinase activity in the A375 melanoma cell line. MCE has not independently confirmed the accuracy of these methods. They are for reference only. Cell Viability AssayCell Line: A375, MeWo melanoma cells, and NHEM cells Concentration: 5 μM, 10 μM, 20 μM, 30 μM, 40 μM, 50 μM, 60 μM Incubation Time: 72 hours Result: Impaired the viability of melanoma cells without affecting the growth of normal melanocytes. Western Blot AnalysisCell Line: A375 cells Concentration: 20 μM Incubation Time: 48 hours, 72 hours Result: Reduced the expression of the active forms of Cdk2 (pCdk2) and cyclin A2, and the phosphorylation of Rb.

Form:Solid

Specifications

Biochemical and Physiological Mechanisms

Salviolone is a natural diterpenoid derivative that can against melanoma cells. Salviolone exhibits a pleiotropic effect against melanoma by hampering cell cycle progression, STAT3 signaling, and malignant phenotype of A375 melanoma cells.

Storage

Protected from light, Store at -20°C

Shipped In

Ice chest + Ice pads

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

Names and Identifiers

• Canonical Smiles: CC1=C(C(=O)C=C2C3=C(C=CC2=C1)C(CCC3)(C)C)O
• IUPAC Name: 9-hydroxy-4,4,8-trimethyl-2,3-dihydro-1H-cyclohepta[a]naphthalen-10-one
• InChIKey: QATRODNHXVHGNU-UHFFFAOYSA-N
• INCHI: 1S/C18H20O2/c1-11-9-12-6-7-15-13(5-4-8-18(15,2)3)14(12)10-16(19)17(11)20/h6-7,9-10H,4-5,8H2,1-3H3,(H,19,20)
• Isomeric SMILES: CC1=C(C(=O)C=C2C3=C(C=CC2=C1)C(CCC3)(C)C)O
• PubChem CID: 10355691
• MeSH Entry Terms: 9-hydroxy-4,4,8-trimethyl-2,3-dihydro-1H-cyclohepta(a)naphthalen-10-one;salviolone
• Molecular Weight: 268.35

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Prenol lipids
      • Subclass Diterpenoids

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Prenol lipids
• Subclass: Diterpenoids
• Intermediate Tree Nodes: Not available
• Direct Parent: Tanshinones, isotanshinones, and derivatives
• Alternative Parents: Tetralins Tropolones Cyclic ketones Organic oxides
• Molecular Framework: Aromatic homopolycyclic compounds
• Substituents: Tanshinone skeleton - Tetralin - Tropolone - Tropone - Benzenoid - Cyclic ketone - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Aromatic homopolycyclic compound
• Description: This compound belongs to the class of organic compounds known as tanshinones, isotanshinones, and derivatives. These are a group of abietane-type norditerpenoid quinones.
• 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

Chemical and Physical Properties

• Molecular Weight: 268.300 g/mol
• XLogP3: 3.100
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 268.146 Da
• Monoisotopic Mass: 268.146 Da
• Topological Polar Surface Area: 37.300 Ų
• Heavy Atom Count: 20
• Formal Charge: 0
• Complexity: 649.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• 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