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Acetylshikonin

CAT: 0804-HY-N2181-01Size: 5 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-N2181-01Size:5 mg
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Description
Acetylshikonin is an oral active anti-cancer, anti-inflammatory, antioxidant, anti-fertility, antibacterial, and neuroprotective agent. Acetylshikonin is a inhibitor of acetylcholinase (AChE) (IC50=34.6 μM) and nonselective cytochrome P450. Acetylshikonin can induce Apoptosis and Autophagy in cancer cells. Acetylshikonin regulates blood glucose, liver fat metabolism, and renal fibrosis, and is used in the study of diabetes, diabetic nephropathy (DN), obesity, and nonalcoholic fatty liver disease (NAFLD) [1][2][3][4][5][6][7][8][9].
CAS Number
24502-78-1
UNSPSC
12352005
Target
Apoptosis; Autophagy; Bacterial; Cytochrome P450
Type
Natural Products
Related Pathways
Anti-infection; Apoptosis; Autophagy; Metabolic Enzyme/Protease
Applications
COVID-19-immunoregulation
Field of Research
Cancer; Infection; Metabolic Disease; Inflammation/Immunology; Neurological Disease
Assay Protocol
https://www.medchemexpress.com/acetylshikonin.html
Purity
99.89
Solubility
DMSO : 50 mg/mL (ultrasonic)
Smiles
O=C1C([C@H](OC(C)=O)C/C=C(C)\C)=CC(C2=C1C(O)=CC=C2O)=O
Molecular Formula
C18H18O6
Molecular Weight
330.33
References & Citations
[1]Li Q, et al. Acetylshikonin from Zicao attenuates cognitive impairment and hippocampus senescence in d-galactose-induced aging mouse model via upregulating the expression of SIRT1. Brain Res Bull. 2018 Mar;137:311-318.|[2] Liu X, et al. Effects of Acetylshikonin on the Infection and Replication of Coxsackievirus A16 in Vitro and in Vivo. J Nat Prod. 2019 May 24;82 (5) :1089-1097.|[3]Huang W, et al. Acetylshikonin stimulates glucose uptake in L6 myotubes via a PLC-β3/PKCδ-dependent pathway. Biomed Pharmacother. 2019 Apr;112:108588. |[4]Su ML, et al. Efficacy of Acetylshikonin in Preventing Obesity and Hepatic Steatosis in db/db Mice. Molecules. 2016 Jul 28;21 (8) :976. |[5]Li Z, et al. Acetylshikonin from Zicao ameliorates renal dysfunction and fibrosis in diabetic mice by inhibiting TGF-β1/Smad pathway. Hum Cell. 2018 Jul;31 (3) :199-209.|[6]Wang P, et al. Acetylshikonin inhibits in vitro and in vivo tumorigenesis in cisplatin-resistant oral cancer cells by inducing autophagy, programmed cell death and targeting m-TOR/PI3K/Akt signalling pathway. J BUON. 2019 Sep-Oct;24 (5) :2062-2067. Retraction in: J BUON. 2021 Jul-Aug;26 (4) :1691. PMID: 31786876.|[7]He Y, et al. Acetylshikonin from Zicao exerts antifertility effects at high dose in rats by suppressing the secretion of GTH. Biochem Biophys Res Commun. 2016 Aug 5;476 (4) :560-565.|[8]Wang Y, et al. Acetylshikonin, a Novel AChE Inhibitor, Inhibits Apoptosis via Upregulation of Heme Oxygenase-1 Expression in SH-SY5Y Cells. Evid Based Complement Alternat Med. 2013;2013:937370. |[9]Shon JC, et al. Acetylshikonin is a novel non-selective cytochrome P450 inhibitor. Biopharm Drug Dispos. 2017 Dec;38 (9) :553-556.
Shipping Conditions
Room Temperature
Storage Conditions
4°C (Powder, protect from light)
Scientific Category
Natural Products
Clinical Information
No Development Reported
Isoform
AChE

Chemical Information

Acetylshikonin

(R)-1-(5,8-Dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl acetate has been reported in Echium italicum, Onosma paniculata, and other organisms with data available.

CAS Number24502-78-1
PubChem CID479501
IUPAC Name[(1R)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-enyl] acetate
Molecular FormulaC18H18O6
Molecular Weight330.3
XLogP3.5
Topological Polar Surface Area101
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count6
Rotatable Bond Count5
Heavy Atom Count24
Formal Charge0
Complexity599
SMILES
CC(=CC[C@H](C1=CC(=O)C2=C(C=CC(=C2C1=O)O)O)OC(=O)C)C
InChI
InChI=1S/C18H18O6/c1-9(2)4-7-15(24-10(3)19)11-8-14(22)16-12(20)5-6-13(21)17(16)18(11)23/h4-6,8,15,20-21H,7H2,1-3H3/t15-/m1/s1
InChIKey
WNFXUXZJJKTDOZ-OAHLLOKOSA-N
Chemical Structure
2D Structure
2D structure of Acetylshikonin
CAS: 24502-78-1
CID: 479501
Formula: C18H18O6
MW: 330.3
Interactive 3D Structure
Loading 3D structure...
Computed Properties
PropertyValue
Molecular Weight330.3
XLogP33.5
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count6
Rotatable Bond Count5
Exact Mass330.11033829
Monoisotopic Mass330.11033829
Topological Polar Surface Area101 Ų
Heavy Atom Count24
Formal Charge0
Complexity599
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes