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Deoxyshikonin

CAT: 0804-HY-N2187-01Size: 5 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-N2187-01Size:5 mg
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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Description
Deoxyshikonin increases the expression of VEGF-C and VEGF-A mRNA in HMVEC-dLy, promotes HIF-1α and HIF-1β subunit interaction and binds to specific DNA sequences targeted by HIF. Deoxyshikonin inhibited colorectal cancer (CRC) through the PI3K/Akt/mTOR pathway. Deoxyshikonin has proangiogenesis effect and antitumor activity. Deoxyshikonin is an antibacterial agent against methicillin-resistant S. aureus (MRSA) and S. pneumonia (MIC=17 μg/mL) [1][2][3].
CAS Number
43043-74-9
UNSPSC
12352005
Hazard Statement
H302, H315, H319, H335
Target
Apoptosis; Bacterial; HIF/HIF Prolyl-Hydroxylase; PI3K
Type
Natural Products
Related Pathways
Anti-infection; Apoptosis; Metabolic Enzyme/Protease; PI3K/Akt/mTOR
Applications
Cancer-programmed cell death
Field of Research
Cancer; Infection; Cardiovascular Disease
Assay Protocol
https://www.medchemexpress.com/deoxyshikonin.html
Concentration
10mM
Purity
99.96
Solubility
DMSO : 33.33 mg/mL (ultrasonic; warming; heat to 60°C)
Smiles
O=C1C(CC/C=C(C)/C)=CC(C2=C1C(O)=CC=C2O)=O
Molecular Formula
C16H16O4
Molecular Weight
272.30
Precautions
H302, H315, H319, H335
References & Citations
[1]Prangsaengtong O, et al. Enhancement of Lymphangiogenesis In Vitro via the Regulations of HIF-1α Expression and Nuclear Translocation by Deoxyshikonin. Evid Based Complement Alternat Med. 2013;2013:148297.|[2]Zhang S, et al. Antibacterial effects of Traditional Chinese Medicine monomers against Streptococcus pneumoniae via inhibiting pneumococcal histidine kinase (VicK) . Front Microbiol. 2015 May 20;6:479.|[3]Yuzhen Zhu, et al. Deoxyshikonin isolated from Arnebia euchromainhibits colorectal cancer by down-regulating the PI3K/Akt/mTOR pathway. Pharm Biol. 2019 Dec;57 (1) :412-423.
Shipping Conditions
Room Temperature
Storage Conditions
4°C (Powder, protect from light)
Scientific Category
Natural Products
Clinical Information
No Development Reported
Isoform
HIF; PI3K

Chemical Information

Deoxyshikonin

Deoxyshikonin is a hydroxy-1,4-naphthoquinone.

CAS Number43043-74-9
PubChem CID98914
IUPAC Name5,8-dihydroxy-2-(4-methylpent-3-enyl)naphthalene-1,4-dione
Molecular FormulaC16H16O4
Molecular Weight272.29
XLogP4.1
Topological Polar Surface Area74.6
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count4
Rotatable Bond Count3
Heavy Atom Count20
Formal Charge0
Complexity471
SMILES
CC(=CCCC1=CC(=O)C2=C(C=CC(=C2C1=O)O)O)C
InChI
InChI=1S/C16H16O4/c1-9(2)4-3-5-10-8-13(19)14-11(17)6-7-12(18)15(14)16(10)20/h4,6-8,17-18H,3,5H2,1-2H3
InChIKey
VOMDIEGPEURZJO-UHFFFAOYSA-N
Chemical Structure
2D Structure
2D structure of Deoxyshikonin
CAS: 43043-74-9
CID: 98914
Formula: C16H16O4
MW: 272.29
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight272.29
XLogP34.1
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count4
Rotatable Bond Count3
Exact Mass272.10485899
Monoisotopic Mass272.10485899
Topological Polar Surface Area74.6 Ų
Heavy Atom Count20
Formal Charge0
Complexity471
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

Alternative Products

CatalogName
GTR19168815-01Deoxyshikonin
371360Deoxyshikonin discontinued

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