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Bruceantin

CAS No.:
41451-75-6
Catalog Number:
AG00C6F2
Molecular Formula:
C28H36O11
Molecular Weight:
548.5788
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
1mg
99%
1 week
United States
$240
- +
5mg
99%
1 week
United States
$640
- +
10mg
99%
1 week
United States
$890
- +
Product Description
Catalog Number:
AG00C6F2
Chemical Name:
Bruceantin
CAS Number:
41451-75-6
Molecular Formula:
C28H36O11
Molecular Weight:
548.5788
MDL Number:
MFCD00866510
IUPAC Name:
methyl (1R,2S,3R,6R,8R,13S,14R,15R,16S,17S)-3-[(E)-3,4-dimethylpent-2-enoyl]oxy-10,15,16-trihydroxy-9,13-dimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-9-ene-17-carboxylate
InChI:
InChI=1S/C28H36O11/c1-11(2)12(3)7-17(30)39-20-22-27-10-37-28(22,25(35)36-6)23(33)19(32)21(27)26(5)9-15(29)18(31)13(4)14(26)8-16(27)38-24(20)34/h7,11,14,16,19-23,31-33H,8-10H2,1-6H3/b12-7+/t14-,16+,19+,20+,21+,22+,23-,26-,27+,28-/m0/s1
InChI Key:
IRQXZTBHNKVIRL-GOTQHHPNSA-N
SMILES:
COC(=O)[C@@]12OC[C@]34[C@H]2[C@@H](OC(=O)/C=C(/C(C)C)\C)C(=O)O[C@@H]4C[C@@H]2[C@]([C@H]3[C@H]([C@@H]1O)O)(C)CC(=O)C(=C2C)O
UNII:
S3NW88DI4T
NSC Number:
165563
Properties
Complexity:
1200  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
10  
Defined Bond Stereocenter Count:
1  
Exact Mass:
548.226g/mol
Formal Charge:
0
Heavy Atom Count:
39  
Hydrogen Bond Acceptor Count:
11  
Hydrogen Bond Donor Count:
3  
Isotope Atom Count:
0
Molecular Weight:
548.585g/mol
Monoisotopic Mass:
548.226g/mol
Rotatable Bond Count:
6  
Topological Polar Surface Area:
166A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
1.7  
Literature
Title Journal
Antitumor Agents. 282. 2'-(R)-O-acetylglaucarubinone, a quassinoid from Odyendyea gabonensis as a potential anti-breast and anti-ovarian cancer agent. Journal of natural products 20100924
NF-kappaB inhibitors from Brucea javanica exhibiting intracellular effects on reactive oxygen species. Anticancer research 20100901
U2504 determines the species specificity of the A-site cleft antibiotics: the structures of tiamulin, homoharringtonine, and bruceantin bound to the ribosome. Journal of molecular biology 20090529
Quassinoid inhibition of AP-1 function does not correlate with cytotoxicity or protein synthesis inhibition. Journal of natural products 20090327
Bioactivity-guided isolation of cytotoxic constituents of Brucea javanica collected in Vietnam. Bioorganic & medicinal chemistry 20090315
Altering chemosensitivity by modulating translation elongation. PloS one 20090101
Synthesis of A/B-ring partial analogs of bruceantin as potential antimalarial agents. Medicinal chemistry (Shariqah (United Arab Emirates)) 20050101
Multiple myeloma regression mediated by bruceantin. Clinical cancer research : an official journal of the American Association for Cancer Research 20040201
Antitumor activity of bruceantin: an old drug with new promise. Journal of natural products 20040201
Novel esters of glaucarubolone as inducers of terminal differentiation of promyelocytic HL-60 cells and inhibitors of 7,12-dimethylbenz[a]anthracene-induced preneoplastic lesion formation in mouse mammary organ culture. Journal of natural products 20011201
Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase. Journal of natural products 19910101
Properties