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Shikonin

Name: Shikonin
Brand: MM

≥98% (HPLC), solid, Pyruvate kinase inhibitor, Calbiochem^®

Synonym(s):

Shikonin, Pyruvate Kinase Inhibitor II

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About This Item

Empirical Formula (Hill Notation):

C₁₆H₁₆O₅

CAS Number:

517-89-5

Molecular Weight:

288.30

UNSPSC Code:

12352200

NACRES:

NA.77

MDL number:

MFCD00075680

Assay:

≥98% (HPLC)

Form:

solid

Storage condition:

OK to freeze, protect from light

Pricing and availability is not currently available.

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Properties

Product Name

Shikonin, A naphthoquinone found in the Chinese herb Shiunko.

Quality Segment

100

description

RTECS - QL8000200

assay

≥98% (HPLC)

form

solid

manufacturer/tradename

Calbiochem^®

storage condition

OK to freeze, protect from light

color

red

solubility

DMSO: 10 mg/mL

shipped in

ambient

storage temp.

−20°C

SMILES string

OC(CC=C(C)C)C1=CC(=O)c2c(c(ccc2O)O)C1=O

InChI

1S/C16H16O5/c1-8(2)3-4-10(17)9-7-13(20)14-11(18)5-6-12(19)15(14)16(9)21/h3,5-7,10,17-19H,4H2,1-2H3

InChI key

NEZONWMXZKDMKF-UHFFFAOYSA-N

Description

General description

A naphthoquinone found in the Chinese herb Lithospermum erythrorhizon. Possesses significant antibacterial, anti-inflammatory and antitumor activities. Inhibits TNF-α and B-16 melanoma-induced angiogenesis in mice. Blocks the expression of integrin αVβ3 and inhibits endothelial cells proliferation and migration in vitro. Also induces apoptosis in HL60 human promyelocytic leukemia cell line. Selectively blocks PKM2 (IC₅₀<1 µM) over PKM1 and PKL activities (IC₅₀ in the range of 10-20 µM), and inhibits cancer cell glycolysis.

Biochem/physiol Actions

Product does not compete with ATP.

Reversible: no

Primary Target
TNF-α-induced and B-16 melanoma-induced angiogenesis

Cell permeable: no

Preparation Note

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.

Other Notes

Chen, J., et al. 2011. Oncogene30, 4297.
Li, H., et al. 1999. Phytother. Res.13, 236.
Yoon, Y., et al. 1999. Planta Med.65, 532.
Hisa, T., et al. 1998. Anticancer Res. 18, 783.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Disclaimer

Toxicity: Standard Handling (A)

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This Item	PHL89791	375680	676484
Sigma-Aldrich 565850 Shikonin	PHL89791 Shikonin	Sigma-Aldrich 375680 Hesperadin	Sigma-Aldrich 676484 VEGFR2 Kinase Inhibitor VI, Ki8751
description A naphthoquinone found in the Chinese herb Shiunko.	description phyproof^® Reference Substance	description Hesperadin primarily used in Inhibition.	description The VEGFR2 Kinase Inhibitor VI, Ki8751, also referenced under CAS 228559-41-9, controls the biological activity of VEGFR2 Kinase. This small molecule/inhibitor is primarily used for Phosphorylation & Dephosphorylation applications.
assay ≥98% (HPLC)	assay ≥98.0% (HPLC)	assay ≥95% (HPLC)	assay ≥97% (HPLC)
form solid	form -	form solid	form solid
Quality Level 100	Quality Level -	Quality Level 100	Quality Level 100
manufacturer/tradename Calbiochem^®	manufacturer/tradename PhytoLab	manufacturer/tradename Calbiochem^®	manufacturer/tradename Calbiochem^®
storage temp. −20°C	storage temp. −20°C	storage temp. −20°C	storage temp. 2-8°C
storage condition protect from light, OK to freeze	storage condition -	storage condition protect from light, OK to freeze	storage condition OK to freeze, protect from light

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Storage Class

11 - Combustible Solids

WGK

WGK 3

Flash Point (°F)

Not applicable

Flash Point (°C)

Not applicable

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