THYMINE ARABINOSIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C10H14N2O6
Molecular Weight	258.228
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=CN([C@@H]2O[C@H](CO)[C@@H](O)[C@@H]2O)C(=O)NC1=O

InChI

InChIKey=DWRXFEITVBNRMK-JAGXHNFQSA-N

InChI=1S/C10H14N2O6/c1-4-2-12(10(17)11-8(4)16)9-7(15)6(14)5(3-13)18-9/h2,5-7,9,13-15H,3H2,1H3,(H,11,16,17)/t5-,6-,7+,9-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C10H14N2O6
Molecular Weight	258.228
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Approval Year

PubMed

Title	Date	PubMed
Voreloxin, a first-in-class anticancer quinolone derivative, acts synergistically with cytarabine in vitro and induces bone marrow aplasia in vivo.	2010-10	20058009
Acute cytotoxicity of arabinofuranosyl nucleoside analogs is not dependent on mitochondrial DNA.	2009-09-10	19481540
Substrate specificity of feline and canine herpesvirus thymidine kinase.	2008-08	18455811
Efficient and selective enzymatic acylation reaction: separation of furanosyl and pyranosyl nucleosides.	2008-07-18	18557651
Characterization and susceptibility to antiviral agents of herpes simplex virus type 1 containing a unique thymidine kinase gene with an amber codon between the first and the second initiation codons.	2008	18066636
N1-substituted thymine derivatives as mitochondrial thymidine kinase (TK-2) inhibitors.	2006-12-28	17181158
Bromovinyl-deoxyuridine: A selective substrate for mitochondrial thymidine kinase in cell extracts.	2006-05-26	16630572
3D-QSAR studies on antitubercular thymidine monophosphate kinase inhibitors based on different alignment methods.	2006-02-15	16290929
The effect of a methyl or 2-fluoroethyl substituent at the N-3 position of thymidine, 3'-fluoro-3'-deoxythymidine and 1-beta-D-arabinosylthymine on their antiviral and cytostatic activity in cell culture.	2006	16542002
Synthesis and in vitro anti-mycobacterial activity of 5-substituted pyrimidine nucleosides.	2005-12-15	16140016
Altered deoxyribonucleotide pools in T-lymphoblastoid cells expressing the multisubstrate nucleoside kinase of Drosophila melanogaster.	2005-08	16045762
Dexamethasone inhibits the HSV-tk/ ganciclovir bystander effect in malignant glioma cells.	2005-04-02	15804364
Inactivity of the bicyclic pyrimidine nucleoside analogues against simian varicella virus (SVV) does not correlate with their substrate activity for SVV-encoded thymidine kinase.	2004-03-19	14985094
Anti-cowpox virus activities of certain adenosine analogs, arabinofuranosyl nucleosides, and 2'-fluoro-arabinofuranosyl nucleosides.	2004	15043161
Lipid-mediated protein delivery of suicide nucleoside kinases.	2003-10-15	14583490
Thymidine and thymidine-5'-O-monophosphate analogues as inhibitors of Mycobacterium tuberculosis thymidylate kinase.	2003-09-15	12941330
Amino acid changes within conserved region III of the herpes simplex virus and human cytomegalovirus DNA polymerases confer resistance to 4-oxo-dihydroquinolines, a novel class of herpesvirus antiviral agents.	2003-02	12525621
Nucleoside analog cytotoxicity and bystander cell killing of cancer cells expressing Drosophila melanogaster deoxyribonucleoside kinase in the nucleus or cytosol.	2001-11-23	11708804
Design, synthesis and enzymatic activity of highly selective human mitochondrial thymidine kinase inhibitors.	2001-05-21	11392548
2'-O-Acyl/alkyl-substituted arabinosyl nucleosides as inhibitors of human mitochondrial thymidine kinase.	2001-03-15	11266658
Mutation of Gln125 to Asn selectively abolishes the thymidylate kinase activity of herpes simplex virus type 1 thymidine kinase.	2001-02	11160865
Phenotypic and genetic characterization of thymidine kinase from clinical strains of varicella-zoster virus resistant to acyclovir.	1999-10	10508017
Efficacy of select antivirals against Cryptosporidium parvum in vitro.	1998-11-01	9812363
Anti-herpesvirus activity profile of 4'-thioarabinofuranosyl purine and uracil nucleosides and activity of 1-beta-D-2'-fluoro-4'-thioarabinofuranosyl guanine and 2,6-diaminopurine against clinical isolates of human cytomegalovirus.	1998-08	9806489
Structure-activity relationship of the affinity of 5-substituted uracil nucleoside analogues for varicella-zoster virus thymidine kinase and their activity against varicella-zoster virus.	1997-08	9298756
Susceptibilities of several drug-resistant herpes simplex virus type 1 strains to alternative antiviral compounds.	1995-07	7492121
Comparative activity of selected antiviral compounds against clinical isolates of varicella-zoster virus.	1995-04	7649195
Synthesis and antiviral activity of phosphonoacetic and phosphonoformic acid esters of 5-bromo-2'-deoxyuridine and related pyrimidine nucleosides and acyclonucleosides.	1989-02	2521518
Efficacies of antiherpesvirus nucleosides against two strains of herpes simplex virus type 1 in Vero and human embryo lung fibroblast cells.	1988-07	2847637
7-Aminoquinolines. A novel class of agents active against herpesviruses.	1988-07	2838633
Comparison of susceptibilities of varicella-zoster virus and herpes simplex viruses to nucleoside analogs.	1986-03	3013088
Influence of twenty potentially antiviral substances on in vitro multiplication of hepatitis A virus.	1986-03	3010855
In vitro and in vivo antiviral activity of 1-beta-D-arabinofuranosyl-E-5-(2-bromovinyl)uracil (BV-araU) and related compounds.	1984-06	6089657
Antiherpes activity of (E)-5-(2-bromovinyl)- and 5-vinyl-1-beta-D-arabinofuranosyluracil and some other 5-substituted uracil arabinosyl nucleosides in two different cell lines.	1983-09	6316849
Comparison of the in vitro and in vivo anti-herpes activities of 1-beta-D-arabinofuranosylthymine and its 5'-monophosphate.	1982-09	6293376
Inhibitory effects of antiherpesviral thymidine analogs against varicella-zoster virus.	1982-02	6280604
In vitro susceptibility of varicella-zoster virus to E-5-(2-bromovinyl)-2'-deoxyuridine and related compounds.	1982-01	6282207
Differential activity of potential antiviral nucleoside analogs on herpes simplex virus-induced and human cellular thymidine kinases.	1981-09	6272634
Antiherpesviral and anticellular effects of 1-beta-D-arabinofuranosyl-E-5-(2-halogenovinyl) uracils.	1981-07	6269482
Antiherpesviral activity and inhibitory action on cell growth of 5-alkenyl derivatives of 1-beta D-arabinofuranosyluracil.	1980-06	6250467
Relative potencies of different anti-herpes agents in the topical treatment of cutaneous herpes simplex virus infection of athymic nude mice.	1979-11	526011
In vitro antiherpesviral activity of 5-alkyl derivatives of 1-beta-D-arabinofuranosyluracil.	1979-08	485126
(E)-5-(2-Bromovinyl)-2'-deoxyuridine: a potent and selective anti-herpes agent.	1979-06	223163
Nucleosides. 110. Synthesis and antiherpes virus activity of some 2'-fluoro-2'-deoxyarabinofuranosylpyrimidine nucleosides.	1979-01	218006

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 22:09:51 GMT 2025` Edited by `admin` on `Mon Mar 31 22:09:51 GMT 2025`
Record UNII	NS9U4BEG7Y
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NSC-68929

Preferred Name

English

THYMINE ARABINOSIDE

Common Name

English

SPONGOTHYMIDIN

Common Name

English

5-METHYLARABINOSYLURACIL

Common Name

English

THYMINE, 1-.BETA.-D-ARABINOFURANOSYL-

Systematic Name

English

ARABINOSYLTHYMINE

Common Name

English

1-.BETA.-D ARABINOFURANOSYLTHYMINE

Common Name

English

SPONGOTHYMIDINE

Common Name

English

1-.BETA.-D-ARABINOFURANOSYLTHYMINE

Common Name

English

2,4(1H,3H)-PYRIMIDINEDIONE, 1-.BETA.-D-ARABINOFURANOSYL-5-METHYL-

Systematic Name

English

Code System Code Type Description

NSC

68929