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1-(3-C-ethynyl-β-D-ribo-pentofuranosyl)cytosine

1-(3-C-ethynyl-β-D-ribo-pentofuranosyl)cytosine structure

CAS No:
180300-43-0
Formula:
C11H13N3O5
Chemical Name:
1-(3-C-ethynyl-β-D-ribo-pentofuranosyl)cytosine
Synonyms:
1-(3-C-ethynyl-β-D-ribo-pentofuranosyl)cytosine;ETHYNYCYTIDINE;ECyd;TAS 106;Ethynylcytidine;4-Amino-1-((2R,3R,4S,5R)-4-ethynyl-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one;cytidine, 3'-c-ethynyl-;Ethynylcytidine (TAS-106)
Categories:
Biochemical Engineering > Saccharides

Description

TAS-106 is a new nucleoside antimetabolite. TAS-106 has demonstrated strong antitumor activity without serious toxicity in nude rat models bearing human tumours.|3'-C-ethynylcytidine is a synthetic cytidine nucleoside containing a covalently bound ethynyl group with potential antineoplastic and radiosensitizing activities. 3'-C-ethynylcytidine is metabolized in tumor cells to ethynylcytidine triphosphate (ECTP), which inhibits RNA synthesis by competitive inhibition of RNA polymerases I, II and III; subsequently, RNase L is activated, resulting in apoptosis. RNase L is a potent antiviral and antiproliferative endoribonuclease that cleaves singled stranded RNA, causes 28s rRNA fragmentation, and activates Janus Kinase (JAK), a mitochondrial-dependent apoptosis signaling molecule.

1-(3-C-ethynyl-β-D-ribo-pentofuranosyl)cytosine Basic Attributes

Molecular Weight：

267.23802

Exact Mass：

267.086

UNII：

Y3O05I09ZK

NCI Thesaurus Code：

C29475

Characteristics

PSA：

129

XLogP3：

-2.7

Density：

1.61±0.1 g/cm3(Predicted)

Melting Point：

233-235 °C

Boiling Point：

536.4±60.0 °C(Predicted)

Flash Point：

278.2ºC

Refractive Index：

1.677

Vapor Pressure：

9.56E-14mmHg at 25°C

Drug Information

Drug Indication：

Investigated for use/treatment in solid tumors and cancer/tumors (unspecified).

Mechanism of Action：

3'-C-ethynylcytidine is metabolized in tumor cells to ethynylcytidine triphosphate (ECTP), which inhibits RNA synthesis by competitive inhibition of RNA polymerases I, II and III; subsequently, RNase L is activated, resulting in apoptosis. RNase L is a potent antiviral and antiproliferative endoribonuclease that cleaves singled stranded RNA, causes 28s rRNA fragmentation, and activates Janus Kinase (JAK), a mitochondrial-dependent apoptosis signaling molecule.

MeSH Entry Terms：

1-(3-C-ethynyl-beta-D-ribo-pentofuranosyl)cytosine

Computed Properties

Molecular Weight:267.24
XLogP3:-2.7
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:3
Exact Mass:267.08552052
Monoisotopic Mass:267.08552052
Topological Polar Surface Area:129
Heavy Atom Count:19
Complexity:508
Defined Atom Stereocenter Count:4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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Guide of 1-(3-C-ethynyl-β-D-ribo-pentofuranosyl)cytosine

Description
Basic Attributes
Characteristics
Drug Information
Computed Properties
Learn More Other Chemicals

1-(3-C-ethynyl-β-D-ribo-pentofuranosyl)cytosine

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