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Thymectacin

CAT: 0804-HY-106168-02Size: 10 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-106168-02Size:10 mg
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Description
Thymectacin (NB1011) is an agent selectively targeting tumor cells that have a high expression of thymidylate synthase (TS) . Thymectacin is an aryloxy phosphoramidate derivative of BVdU (brivudin) [1][2].
CAS Number
232925-18-7
Product Name Alternative
NB1011
UNSPSC
12352005
Target
Thymidylate Synthase
Type
Reference compound
Related Pathways
Apoptosis
Applications
Cancer-programmed cell death
Field of Research
Cancer
Assay Protocol
https://www.medchemexpress.com/thymectacin.html
Purity
98.21
Solubility
DMSO : 100 mg/mL (ultrasonic)
Smiles
O[C@H]1C[C@H](N2C=C(/C=C/Br)C(NC2=O)=O)O[C@@H]1COP(N[C@@H](C)C(OC)=O)(OC3=CC=CC=C3)=O
Molecular Formula
C21H25BrN3O9P
Molecular Weight
574.32
References & Citations
[1]Wilson RH. Novel therapeutic developments other than EGFR and VEGF inhibition in colorectal cancer. Oncologist. 2006;11 (9) :1018-1024.|[2] Congiatu C, et al. Novel potential anticancer naphthyl phosphoramidates of BVdU: separation of diastereoisomers and assignment of the absolute configuration of the phosphorus center. J Med Chem. 2006;49 (2) :452-455.
Shipping Conditions
Room Temperature
Storage Conditions
-20°C, 3 years; 4°C, 2 years (Powder)
Scientific Category
Reference compound1
Clinical Information
Phase 2

Chemical Information

N-(5-((1E)-2-Bromoethenyl)-2'-deoxy-P-phenyl-5'-uridylyl)-L-alanine methyl ester

Thymectacin, a phosphoramidate derivative of (E)-5-(2-bromovinyl)-2'-deoxyuridine, is a novel small molecule anticancer agent. Thymectacin is selectively active against tumor cells expressing high levels of thymidylate synthase (TS), a critical enzyme in DNA biosynthesis. Thymectacin was as efficacious as irinotecan, a drug recently approved for the treatment of 5-fluorouracil-resistant colon cancer.

CAS Number232925-18-7
PubChem CID6440764
IUPAC Namemethyl (2S)-2-[[[(2R,3S,5R)-5-[5-[(E)-2-bromoethenyl]-2,4-dioxopyrimidin-1-yl]-3-hydroxyoxolan-2-yl]methoxy-phenoxyphosphoryl]amino]propanoate
Molecular FormulaC21H25BrN3O9P
Molecular Weight574.3
XLogP1.1
Topological Polar Surface Area153
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count10
Rotatable Bond Count11
Heavy Atom Count35
Formal Charge0
Complexity908
SMILES
C[C@@H](C(=O)OC)NP(=O)(OC[C@@H]1[C@H](C[C@@H](O1)N2C=C(C(=O)NC2=O)/C=C/Br)O)OC3=CC=CC=C3
InChI
InChI=1S/C21H25BrN3O9P/c1-13(20(28)31-2)24-35(30,34-15-6-4-3-5-7-15)32-12-17-16(26)10-18(33-17)25-11-14(8-9-22)19(27)23-21(25)29/h3-9,11,13,16-18,26H,10,12H2,1-2H3,(H,24,30)(H,23,27,29)/b9-8+/t13-,16-,17+,18+,35?/m0/s1
InChIKey
CFBLUORPOFELCE-BACVZHSASA-N
Chemical Structure
2D Structure
2D structure of N-(5-((1E)-2-Bromoethenyl)-2'-deoxy-P-phenyl-5'-uridylyl)-L-alanine methyl ester
CAS: 232925-18-7
CID: 6440764
Formula: C21H25BrN3O9P
MW: 574.3
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight574.3
XLogP31.1
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count10
Rotatable Bond Count11
Exact Mass573.05118
Monoisotopic Mass573.05118
Topological Polar Surface Area153 Ų
Heavy Atom Count35
Formal Charge0
Complexity908
Isotope Atom Count0
Defined Atom Stereocenter Count4
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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CatalogName
T24881-01Thymectacin

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