Home Other Building Blocks Oxacyclohexadec-13-ene-2,6-dione, 4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[(1E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-, (4S,7R,8S,9S,13Z,16S)-

Oxacyclohexadec-13-ene-2,6-dione, 4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[(1E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-, (4S,7R,8S,9S,13Z,16S)-

CAS No.:
189453-10-9
Catalog Number:
AG002DOU
Molecular Formula:
C27H41NO5S
Molecular Weight:
491.6831
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
1mg
≥99%
1 week
United States
$147
- +
5mg
≥99%
1 week
United States
$260
- +
10mg
99%
1 week
United States
$390
- +
25mg
99%
1 week
United States
$835
- +
50mg
99%
1 week
United States
$1515
- +
100mg
99%
1 week
United States
$2765
- +
Product Description
Catalog Number:
AG002DOU
Chemical Name:
Oxacyclohexadec-13-ene-2,6-dione, 4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[(1E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-, (4S,7R,8S,9S,13Z,16S)-
CAS Number:
189453-10-9
Molecular Formula:
C27H41NO5S
Molecular Weight:
491.6831
MDL Number:
MFCD27976357
IUPAC Name:
(4S,7R,8S,9S,13Z,16S)-4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[(E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadec-13-ene-2,6-dione
InChI:
InChI=1S/C27H41NO5S/c1-16-9-8-10-17(2)25(31)19(4)26(32)27(6,7)23(29)14-24(30)33-22(12-11-16)18(3)13-21-15-34-20(5)28-21/h11,13,15,17,19,22-23,25,29,31H,8-10,12,14H2,1-7H3/b16-11-,18-13+/t17-,19+,22-,23-,25-/m0/s1
InChI Key:
XOZIUKBZLSUILX-GIQCAXHBSA-N
SMILES:
O=C1O[C@@H](C/C=C(/C)\CCC[C@@H]([C@@H]([C@H](C(=O)C([C@H](C1)O)(C)C)C)O)C)/C(=C/c1csc(n1)C)/C
UNII:
T0358E0YUF
Properties
Complexity:
777  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
5  
Defined Bond Stereocenter Count:
2  
Exact Mass:
491.271g/mol
Formal Charge:
0
Heavy Atom Count:
34  
Hydrogen Bond Acceptor Count:
7  
Hydrogen Bond Donor Count:
2  
Isotope Atom Count:
0
Molecular Weight:
491.687g/mol
Monoisotopic Mass:
491.271g/mol
Rotatable Bond Count:
2  
Topological Polar Surface Area:
125A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
5  
Literature
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Epothilones induce human colon cancer SW620 cell apoptosis via the tubulin polymerization independent activation of the nuclear factor-kappaB/IkappaB kinase signal pathway. Molecular cancer therapeutics 20071001
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Alterations in gamma-actin and tubulin-targeted drug resistance in childhood leukemia. Journal of the National Cancer Institute 20061004
Determination of desoxyepothilone B in nude mice plasma by liquid-liquid extraction and reversed-phase high-performance liquid chromatography. Journal of pharmaceutical and biomedical analysis 20060918
Heterologous production of epothilone C and D in Escherichia coli. Biochemistry 20060131
Current state of the art of new tubulin inhibitors in the clinic. Current clinical pharmacology 20060101
Total synthesis of 12,13-desoxyepothilone B (Epothilone D). Bioorganic chemistry 20050401
Total syntheses of epothilones B and d. The Journal of organic chemistry 20041224
Kinetics and mechanism of degradation of epothilone-D: an experimental anticancer agent. Journal of pharmaceutical sciences 20041201
A comparison of signaling activities induced by Taxol and desoxyepothilone B. Journal of chemotherapy (Florence, Italy) 20041201
Crystal structures of epothilone D-bound, epothilone B-bound, and substrate-free forms of cytochrome P450epoK. The Journal of biological chemistry 20031107
Creating polyketide diversity through genetic engineering. Frontiers in bioscience : a journal and virtual library 20030101
Probing the SAR of dEpoB via chemical synthesis: a total synthesis evaluation of C26-(1,3-dioxolanyl)-12,13-desoxyepothilone B. The Journal of organic chemistry 20021101
A new cytotoxic epothilone from modified polyketide synthases heterologously expressed in Myxococcus xanthus. Journal of natural products 20020701
Optimizing the heterologous production of epothilone D in Myxococcus xanthus. Biotechnology and bioengineering 20020505
Large-scale isolation and crystallization of epothilone D from Myxococcus xanthus cultures. Journal of natural products 20020401
Total synthesis of epothilones B and D. Organic letters 20010712
New natural epothilones from Sorangium cellulosum, strains So ce90/B2 and So ce90/D13: isolation, structure elucidation, and SAR studies. Journal of natural products 20010701
Total synthesis of epothilone B, epothilone D, and cis- and trans-9,10-dehydroepothilone D. Journal of the American Chemical Society 20010613
Catalytic antibody route to the naturally occurring epothilones: total synthesis of epothilones A-F. Chemistry (Weinheim an der Bergstrasse, Germany) 20010417
Properties