Home Other Building Blocks 1,4-Naphthalenedione, 2-[(1R)-1-(acetyloxy)-4-methyl-3-penten-1-yl]-5,8-dihydroxy-

1,4-Naphthalenedione, 2-[(1R)-1-(acetyloxy)-4-methyl-3-penten-1-yl]-5,8-dihydroxy-

CAS No.:
24502-78-1
Catalog Number:
AG002OCT
Molecular Formula:
C18H18O6
Molecular Weight:
330.3319
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Product Description
Catalog Number:
AG002OCT
Chemical Name:
1,4-Naphthalenedione, 2-[(1R)-1-(acetyloxy)-4-methyl-3-penten-1-yl]-5,8-dihydroxy-
CAS Number:
24502-78-1
Molecular Formula:
C18H18O6
Molecular Weight:
330.3319
MDL Number:
MFCD00143538
IUPAC Name:
[(1R)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-enyl] acetate
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
InChI Key:
WNFXUXZJJKTDOZ-OAHLLOKOSA-N
SMILES:
CC(=O)O[C@@H](C1=CC(=O)c2c(C1=O)c(O)ccc2O)CC=C(C)C
Properties
Complexity:
599  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
1  
Defined Bond Stereocenter Count:
0
Exact Mass:
330.11g/mol
Formal Charge:
0
Heavy Atom Count:
24  
Hydrogen Bond Acceptor Count:
6  
Hydrogen Bond Donor Count:
2  
Isotope Atom Count:
0
Molecular Weight:
330.336g/mol
Monoisotopic Mass:
330.11g/mol
Rotatable Bond Count:
5  
Topological Polar Surface Area:
101A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
3.5  
Literature
Title Journal
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Naphthoquinones from Onosma paniculata induce cell-cycle arrest and apoptosis in melanoma Cells. Journal of natural products 20120525
Ionization of shikonin derivatives using negative-ion electrospray mass spectrometry: [M-H]- versus [M + e]•-. Journal of mass spectrometry : JMS 20120501
Selective and slow-binding inhibition of shikonin derivatives isolated from Lithospermum erythrorhizon on glycosyl hydrolase 33 and 34 sialidases. Bioorganic & medicinal chemistry 20120301
Callus culture of Echium italicum L. towards production of a shikonin derivative. Natural product research 20110901
The anti-proliferation effect of Aikete injection on hepatocellular carcinoma in vitro and in vivo. Pharmaceutical biology 20110501
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Inhibitory effect of acetylshikonin on human gastric carcinoma cell line SGC-7901 in vitro and in vivo. World journal of gastroenterology 20090421
The influence of acetylshikonin, a natural naphthoquinone, on the production of leukotriene B4 and thromboxane A2 in rat neutrophils. European journal of pharmacology 20090401
Quantitative determination of acetylshikonin in macaque monkey blood by LC-ESI-MS/MS after precolumn derivatization with 2-mercaptoethanol and its application in pharmacokinetic study. Acta pharmacologica Sinica 20081201
Modulation of orphan nuclear receptor Nur77-mediated apoptotic pathway by acetylshikonin and analogues. Cancer research 20081101
Shikonin, acetylshikonin, and isobutyroylshikonin inhibit VEGF-induced angiogenesis and suppress tumor growth in lewis lung carcinoma-bearing mice. Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan 20081101
Comparison of the cytotoxic activities of naturally occurring hydroxyanthraquinones and hydroxynaphthoquinones. European journal of medicinal chemistry 20080601
Isolation and purification of acetylshikonin and beta-acetoxyisovalerylshikonin from cell suspension cultures of Arnebia euchroma (Royle) Johnston using rapid preparative HPLC. Journal of separation science 20080301
Synthetic 2',5'-dimethoxychalcones as G(2)/M arrest-mediated apoptosis-inducing agents and inhibitors of nitric oxide production in rat macrophages. European journal of medicinal chemistry 20070501
Human ACAT inhibitory effects of shikonin derivatives from Lithospermum erythrorhizon. Bioorganic & medicinal chemistry letters 20070215
Evaluation of the anti-inflammatory and cytotoxic activities of naphthazarine derivatives from Onosma leptantha. Phytomedicine : international journal of phytotherapy and phytopharmacology 20060301
The effect of acetylshikonin isolated from Lithospermum canescens roots on tumor-induced cutaneous angiogenesis. Acta poloniae pharmaceutica 20040101
Antimicrobial activities of naphthazarins from Arnebia euchroma. Journal of natural products 20021201
Shikonin derivatives: synthesis and inhibition of human telomerase. Bioorganic & medicinal chemistry letters 20020520
Properties