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Rocaglamide

CAS No.:
84573-16-0
Catalog Number:
AG008HI1
Molecular Formula:
C29H31NO7
Molecular Weight:
505.5589
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
1mg
99%
1 week
United States
$404
- +
5mg
99%
1 week
United States
$960
- +
10mg
99%
1 week
United States
$1654
- +
25mg
99%
1 week
United States
$3043
- +
50mg
99%
1 week
United States
$5265
- +
100mg
99%
1 week
United States
$8321
- +
Product Description
Catalog Number:
AG008HI1
Chemical Name:
Rocaglamide
CAS Number:
84573-16-0
Molecular Formula:
C29H31NO7
Molecular Weight:
505.5589
MDL Number:
MFCD08702699
IUPAC Name:
(1R,2R,3S,3aR,8bS)-1,8b-dihydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-N,N-dimethyl-3-phenyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-2-carboxamide
InChI:
InChI=1S/C29H31NO7/c1-30(2)27(32)23-24(17-9-7-6-8-10-17)29(18-11-13-19(34-3)14-12-18)28(33,26(23)31)25-21(36-5)15-20(35-4)16-22(25)37-29/h6-16,23-24,26,31,33H,1-5H3/t23-,24-,26-,28+,29+/m1/s1
InChI Key:
DAPAQENNNINUPW-IDAMAFBJSA-N
SMILES:
COc1ccc(cc1)[C@]12Oc3c([C@]2(O)[C@@H]([C@@H]([C@H]1c1ccccc1)C(=O)N(C)C)O)c(OC)cc(c3)OC
NSC Number:
326408
Properties
Complexity:
810  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
5  
Defined Bond Stereocenter Count:
0
Exact Mass:
505.21g/mol
Formal Charge:
0
Heavy Atom Count:
37  
Hydrogen Bond Acceptor Count:
7  
Hydrogen Bond Donor Count:
2  
Isotope Atom Count:
0
Molecular Weight:
505.567g/mol
Monoisotopic Mass:
505.21g/mol
Rotatable Bond Count:
6  
Topological Polar Surface Area:
97.7A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
2.8  
Literature
Title Journal
Total synthesis of (±)-rocaglamide via oxidation-initiated Nazarov cyclization. The Journal of organic chemistry 20120217
Synthesis of rocaglamide hydroxamates and related compounds as eukaryotic translation inhibitors: synthetic and biological studies. Journal of medicinal chemistry 20120112
Inhibitors of translation targeting eukaryotic translation initiation factor 4A. Methods in enzymology 20120101
Cytotoxic and NF-κB inhibitory constituents of the stems of Cratoxylum cochinchinense and their semisynthetic analogues. Journal of natural products 20110527
Resorcylic acid lactones with cytotoxic and NF-κB inhibitory activities and their structure-activity relationships. Journal of natural products 20110527
Cytotoxic and NF-kappaB inhibitory constituents of Artocarpus rigida. Journal of natural products 20100528
Cytotoxic xanthone constituents of the stem bark of Garcinia mangostana (mangosteen). Journal of natural products 20091101
Nazarov cyclization initiated by peracid oxidation: the total synthesis of (+/-)-rocaglamide. Journal of the American Chemical Society 20090610
Bioactive 5,6-dihydro-alpha-pyrone derivatives from Hyptis brevipes. Journal of natural products 20090601
Stereoselective synthesis of the rocaglamide skeleton via a silyl vinylketene formation/[4 + 1] annulation sequence. Organic letters 20081002
Ponapensin, a cyclopenta[bc]benzopyran with potent NF-kappaB inhibitory activity from Aglaia ponapensis. Bioorganic & medicinal chemistry letters 20070101
Potential of cyclopenta[b]benzofurans from Aglaia species in cancer chemotherapy. Anti-cancer agents in medicinal chemistry 20060701
Microsphere-based protease assays and screening application for lethal factor and factor Xa. Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501
A biomimetic approach to the rocaglamides employing photogeneration of oxidopyryliums derived from 3-hydroxyflavones. Journal of the American Chemical Society 20041027
Rocaglamide derivatives are potent inhibitors of NF-kappa B activation in T-cells. The Journal of biological chemistry 20021122
Rocaglamides, glycosides, and putrescine bisamides from Aglaia dasyclada. Journal of natural products 20010901
New insecticidal rocaglamide derivatives and related compounds from Aglaia oligophylla. Journal of natural products 20010401
Properties