Home Other Building Blocks Taltobulin

Taltobulin

CAS No.:
228266-40-8
Catalog Number:
AG00BF4U
Molecular Formula:
C27H43N3O4
Molecular Weight:
473.6480
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
5mg
99%
1 week
United States
$279
- +
10mg
99%
1 week
United States
$390
- +
50mg
99%
1 week
United States
$1237
- +
Product Description
Catalog Number:
AG00BF4U
Chemical Name:
Taltobulin
CAS Number:
228266-40-8
Molecular Formula:
C27H43N3O4
Molecular Weight:
473.6480
MDL Number:
MFCD07772353
IUPAC Name:
(E,4S)-4-[[(2S)-3,3-dimethyl-2-[[(2S)-3-methyl-2-(methylamino)-3-phenylbutanoyl]amino]butanoyl]-methylamino]-2,5-dimethylhex-2-enoic acid
InChI:
InChI=1S/C27H43N3O4/c1-17(2)20(16-18(3)25(33)34)30(10)24(32)22(26(4,5)6)29-23(31)21(28-9)27(7,8)19-14-12-11-13-15-19/h11-17,20-22,28H,1-10H3,(H,29,31)(H,33,34)/b18-16+/t20-,21-,22-/m1/s1
InChI Key:
CNTMOLDWXSVYKD-PSRNMDMQSA-N
SMILES:
CN[C@@H](C(c1ccccc1)(C)C)C(=O)N[C@@H](C(C)(C)C)C(=O)N([C@@H](C(C)C)/C=C(/C(=O)O)\C)C
UNII:
J6D6912BXS
Properties
Complexity:
746  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
3  
Defined Bond Stereocenter Count:
1  
Exact Mass:
473.325g/mol
Formal Charge:
0
Heavy Atom Count:
34  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
3  
Isotope Atom Count:
0
Molecular Weight:
473.658g/mol
Monoisotopic Mass:
473.325g/mol
Rotatable Bond Count:
11  
Topological Polar Surface Area:
98.7A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
2.6  
Literature
Title Journal
Mitochondrial dysfunction confers resistance to multiple drugs in Caenorhabditis elegans. Molecular biology of the cell 20100315
Absolute configurations of tubulin inhibitors taltobulin (HTI-286) and HTI-042 characterized by X-ray diffraction analysis and NMR studies. Bioorganic & medicinal chemistry letters 20100301
Total synthesis and biological evaluation of tubulysin U, tubulysin V, and their analogues. Journal of medicinal chemistry 20090122
Targeting prostate cancer with HTI-286, a synthetic analog of the marine sponge product hemiasterlin. International journal of cancer 20080515
Tubulysin analogs incorporating desmethyl and dimethyl tubuphenylalanine derivatives. Bioorganic & medicinal chemistry letters 20080501
Inhibition of hepatic tumor cell proliferation in vitro and tumor growth in vivo by taltobulin, a synthetic analogue of the tripeptide hemiasterlin. World journal of gastroenterology 20061114
Two photoaffinity analogues of the tripeptide, hemiasterlin, exclusively label alpha-tubulin. Biochemistry 20050510
Tumor cells resistant to a microtubule-depolymerizing hemiasterlin analogue, HTI-286, have mutations in alpha- or beta-tubulin and increased microtubule stability. Biochemistry 20041109
Cells resistant to HTI-286 do not overexpress P-glycoprotein but have reduced drug accumulation and a point mutation in alpha-tubulin. Molecular cancer therapeutics 20041001
Synthesis and biological activity of analogues of the antimicrotubule agent N,beta,beta-trimethyl-L-phenylalanyl-N(1)-[(1S,2E)-3-carboxy-1-isopropylbut-2-enyl]- N(1),3-dimethyl-L-valinamide (HTI-286). Journal of medicinal chemistry 20040909
Probing the interaction of HTI-286 with tubulin using a stilbene analogue. Journal of the American Chemical Society 20040818
D-piece modifications of the hemiasterlin analog HTI-286 produce potent tubulin inhibitors. Bioorganic & medicinal chemistry letters 20040816
Targeting vascular and avascular compartments of tumors with C. novyi-NT and anti-microtubule agents. Cancer biology & therapy 20040301
Biophysical characterization of the interactions of HTI-286 with tubulin heterodimer and microtubules. Biochemistry 20031125
HTI-286, a synthetic analogue of the tripeptide hemiasterlin, is a potent antimicrotubule agent that circumvents P-glycoprotein-mediated resistance in vitro and in vivo. Cancer research 20030415
Properties