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Silvestrol

CAS No.:
697235-38-4
Catalog Number:
AG00FC11
Molecular Formula:
C34H38O13
Molecular Weight:
654.6577
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
1mg
98%
1 week
United States
$1223
- +
2mg
98%
1 week
United States
$2140
- +
5mg
98%
1 week
United States
$4501
- +
10mg
98%
1 week
United States
$6307
- +
Product Description
Catalog Number:
AG00FC11
Chemical Name:
Silvestrol
CAS Number:
697235-38-4
Molecular Formula:
C34H38O13
Molecular Weight:
654.6577
MDL Number:
MFCD22417097
IUPAC Name:
methyl (1R,2R,3S,3aR,8bS)-6-[[(2S,3R,6R)-6-[(1R)-1,2-dihydroxyethyl]-3-methoxy-1,4-dioxan-2-yl]oxy]-1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-2-carboxylate
InChI:
InChI=1S/C34H38O13/c1-40-20-12-10-19(11-13-20)34-27(18-8-6-5-7-9-18)26(30(38)42-3)29(37)33(34,39)28-23(41-2)14-21(15-24(28)47-34)45-32-31(43-4)44-17-25(46-32)22(36)16-35/h5-15,22,25-27,29,31-32,35-37,39H,16-17H2,1-4H3/t22-,25-,26-,27-,29-,31-,32-,33+,34+/m1/s1
InChI Key:
GVKXFVCXBFGBCD-QKDMMWSPSA-N
SMILES:
OC[C@H]([C@H]1CO[C@H]([C@@H](O1)Oc1cc2O[C@@]3([C@@](c2c(c1)OC)(O)[C@@H]([C@@H]([C@H]3c1ccccc1)C(=O)OC)O)c1ccc(cc1)OC)OC)O
Properties
Complexity:
1050  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
9  
Defined Bond Stereocenter Count:
0
Exact Mass:
654.231g/mol
Formal Charge:
0
Heavy Atom Count:
47  
Hydrogen Bond Acceptor Count:
13  
Hydrogen Bond Donor Count:
4  
Isotope Atom Count:
0
Molecular Weight:
654.665g/mol
Monoisotopic Mass:
654.231g/mol
Rotatable Bond Count:
11  
Topological Polar Surface Area:
172A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
1.6  
Literature
Title Journal
Synthetic silvestrol analogues as potent and selective protein synthesis inhibitors. Journal of medicinal chemistry 20121025
Total synthesis of 2''',5'''-diepisilvestrol and its C1''' epimer: key structure activity relationships at C1''' and C2'''. Journal of natural products 20120824
Synthesis of rocaglamide hydroxamates and related compounds as eukaryotic translation inhibitors: synthetic and biological studies. Journal of medicinal chemistry 20120112
Resistance to the translation initiation inhibitor silvestrol is mediated by ABCB1/P-glycoprotein overexpression in acute lymphoblastic leukemia cells. The AAPS journal 20110901
The relevance of higher plants in lead compound discovery programs. Journal of natural products 20110624
Resorcylic acid lactones with cytotoxic and NF-κB inhibitory activities and their structure-activity relationships. Journal of natural products 20110527
Isolation and characterization of minor analogues of silvestrol and other constituents from a large-scale re-collection of Aglaia foveolata. Journal of natural products 20101129
Synergistic effect of inhibiting translation initiation in combination with cytotoxic agents in acute myelogenous leukemia cells. Leukemia research 20100401
Inhibitors of translation initiation as cancer therapeutics. Future medicinal chemistry 20091201
Synthetic analogue of rocaglaol displays a potent and selective cytotoxicity in cancer cells: involvement of apoptosis inducing factor and caspase-12. Journal of medicinal chemistry 20090827
Total synthesis of the potent anticancer Aglaia metabolites (-)-silvestrol and (-)-episilvestrol and the active analogue (-)-4'-desmethoxyepisilvestrol. Journal of the American Chemical Society 20090204
Antitumor activity and mechanism of action of the cyclopenta[b]benzofuran, silvestrol. PloS one 20090101
Therapeutic suppression of translation initiation modulates chemosensitivity in a mouse lymphoma model. The Journal of clinical investigation 20080701
Silvestrol, a potential anticancer rocaglate derivative from Aglaia foveolata, induces apoptosis in LNCaP cells through the mitochondrial/apoptosome pathway without activation of executioner caspase-3 or -7. Anticancer research 20070101
Total synthesis of (-)-episilvestrol and (-)-silvestrol. Angewandte Chemie (International ed. in English) 20070101
Silvestrol regulates G2/M checkpoint genes independent of p53 activity. Anticancer research 20060101
Silvestrol and episilvestrol, potential anticancer rocaglate derivatives from Aglaia silvestris. The Journal of organic chemistry 20040514
Properties