Home Other Building Blocks 1,4-Naphthalenedione,5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-

1,4-Naphthalenedione,5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-

CAS No.:
54952-43-1
Catalog Number:
AG019EK4
Molecular Formula:
Molecular Weight:
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Product Description
Catalog Number:
AG019EK4
Chemical Name:
1,4-Naphthalenedione,5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-
CAS Number:
54952-43-1
MDL Number:
MFCD00016668
IUPAC Name:
5,8-dihydroxy-2-(1-hydroxy-4-methylpent-3-enyl)naphthalene-1,4-dione
InChI:
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
Properties
Complexity:
501  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
288.1g/mol
Formal Charge:
0
Heavy Atom Count:
21  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
3  
Isotope Atom Count:
0
Molecular Weight:
288.299g/mol
Monoisotopic Mass:
288.1g/mol
Rotatable Bond Count:
3  
Topological Polar Surface Area:
94.8A^2
Undefined Atom Stereocenter Count:
1  
Undefined Bond Stereocenter Count:
0
XLogP3:
3  
Literature
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Shikonin suppresses proliferation and induces cell cycle arrest through the inhibition of hypoxia-inducible factor-1α signaling. Chemico-biological interactions 20170825
Functional and mechanistic investigation of Shikonin in scarring. Chemico-biological interactions 20150225
Shikonin, a constituent of Lithospermum erythrorhizon exhibits anti-allergic effects by suppressing orphan nuclear receptor Nr4a family gene expression as a new prototype of calcineurin inhibitors in mast cells. Chemico-biological interactions 20141205
Shikonin time-dependently induced necrosis or apoptosis in gastric cancer cells via generation of reactive oxygen species. Chemico-biological interactions 20140325
Shikonin attenuates lung cancer cell adhesion to extracellular matrix and metastasis by inhibiting integrin β1 expression and the ERK1/2 signaling pathway. Toxicology 20130607
Shikonin induces programmed necrosis-like cell death through the formation of receptor interacting protein 1 and 3 complex. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20130501
Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis. Bioorganic & medicinal chemistry letters 20101101
[Effect of shikonin, a phytocompound from Lithospermum erythrorhizon, on rat vascular smooth muscle cells proliferation and apoptosis in vitro]. Zhonghua yi xue za zhi 20050608
Screening of the inhibitory effect of vegetable constituents on the aryl hydrocarbon receptor-mediated activity induced by 2,3,7,8-tetrachlorodibenzo-p-dioxin. Biological & pharmaceutical bulletin 20031201
Shikonin derivatives: synthesis and inhibition of human telomerase. Bioorganic & medicinal chemistry letters 20020520
Properties