β-Hydroxyisovalerylshikonin - ≥99% , CAS No.7415-78-3

CAS: 7415-78-3 Cat. No.: H648056 Molecular Weight: 388.41 PubChem CID: 100203

GRADE & PURITY ≥99%

Synonyms

3'-Hydroxyisovalerylshikonin; (c)micro-Hydroxyisovalerylshikonin | InChI=1/C21H24O7/c1-11(2)5-8-16(28-17(25)10-21(3,4)27)12-9-15(24)18-13(22)6-7-14(23)19(18)20(12)26/h5-7,9,16,22-23,27H,8,10H2,1-4H3 | NSC110263 | NSC-110263 | beta-Hydroxyisovalerylshikoni

Storage

Protected from light,Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

Beta-hydroxyisovalerylshikonin is a natural product isolated from Lithospermum erythrorhizon , acts as a potent inhibitor of protein tyrosine kinases (PTK) , with IC 50 s of 0.7μM and 1μM for EGFR and v-Src receptor, respectively. Beta-hydroxyisovalerylshikonin is effective against a wide variety of tumor cell lines, and most efficiently induces cell-death in NCI-H522 and DMS114 cells

Form:Solid

IC50& Target:IC50: 0.7 μM (EGFR), 1 μM (v-Src)

Specifications

Synonyms

3'-Hydroxyisovalerylshikonin; (c)micro-Hydroxyisovalerylshikonin | InChI=1/C21H24O7/c1-11(2)5-8-16(28-17(25)10-21(3, 4)27)12-9-15(24)18-13(22)6-7-14(23)19(18)20(12)26/h5-7, 9, 16, 22-23, 27H, 8, 10H2, 1-4H3 | NSC110263 | NSC-110263 | beta-Hydroxyisovalerylshikoni

Specifications & Purity

≥99%

Biochemical and Physiological Mechanisms

Beta-hydroxyisovalerylshikonin is a natural product isolated from Lithospermum erythrorhizon , acts as a potent inhibitor of protein tyrosine kinases (PTK) , with IC 50 s of 0.7μM and 1μM for EGFR and v-Src receptor, respectively. Beta-hydroxyisovalerylsh

Storage

Protected from light, 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.

Purity

≥99%

Names and Identifiers

• Canonical Smiles: CC(=CCC(C1=CC(=O)C2=C(C=CC(=C2C1=O)O)O)OC(=O)CC(C)(C)O)C
• IUPAC Name: [1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-enyl] 3-hydroxy-3-methylbutanoate
• InChIKey: MXANJRGHSFELEJ-UHFFFAOYSA-N
• INCHI: 1S/C21H24O7/c1-11(2)5-8-16(28-17(25)10-21(3,4)27)12-9-15(24)18-13(22)6-7-14(23)19(18)20(12)26/h5-7,9,16,22-23,27H,8,10H2,1-4H3
• Isomeric SMILES: CC(=CCC(C1=CC(=O)C2=C(C=CC(=C2C1=O)O)O)OC(=O)CC(C)(C)O)C
• Alternate CAS: 7415-78-3,87798-74-1
• PubChem CID: 100203
• NSC Number: 110263
• MeSH Entry Terms: beta-HIVS;beta-hydroxyisovalerylshikonin
• Molecular Weight: 388.41

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Naphthalenes
      • Subclass Naphthoquinones

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Naphthalenes
• Subclass: Naphthoquinones
• Intermediate Tree Nodes: Not available
• Direct Parent: Naphthoquinones
• Alternative Parents: Bicyclic monoterpenoids Aromatic monoterpenoids Quinones Aryl ketones Fatty acid esters 1-hydroxy-2-unsubstituted benzenoids Vinylogous acids Tertiary alcohols Carboxylic acid esters Monocarboxylic acids and derivatives Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homopolycyclic compounds
• Substituents: Naphthoquinone - Aromatic monoterpenoid - Bicyclic monoterpenoid - Monoterpenoid - Aryl ketone - Quinone - 1-hydroxy-2-unsubstituted benzenoid - Fatty acid ester - Fatty acyl - Vinylogous acid - Tertiary alcohol - Ketone - Carboxylic acid ester - Monocarboxylic acid or derivatives - Carboxylic acid derivative - Alcohol - Hydrocarbon derivative - Carbonyl group - Organic oxide - Organic oxygen compound - Organooxygen compound - Aromatic homopolycyclic compound
• Description: This compound belongs to the class of organic compounds known as naphthoquinones. These are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone).
• 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

• Solubility: DMSO : 10 mg/mL (25.75 mM; ultrasonic and warming and heat to 60°C)
• Molecular Weight: 388.400 g/mol
• XLogP3: 3.400
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 7
• Exact Mass: 388.152 Da
• Monoisotopic Mass: 388.152 Da
• Topological Polar Surface Area: 121.000 Ų
• Heavy Atom Count: 28
• Formal Charge: 0
• Complexity: 700.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 1
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1