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Details

Stereochemistry ABSOLUTE
Molecular Formula C10H13N5O5S
Molecular Weight 315.306
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 8-THIOGUANOSINE

SMILES

NC1=NC2=C(NC(=S)N2[C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)C(=O)N1

InChI

InChIKey=KZELNMSPWPFAEB-UMMCILCDSA-N
InChI=1S/C10H13N5O5S/c11-9-13-6-3(7(19)14-9)12-10(21)15(6)8-5(18)4(17)2(1-16)20-8/h2,4-5,8,16-18H,1H2,(H,12,21)(H3,11,13,14,19)/t2-,4-,5-,8-/m1/s1

HIDE SMILES / InChI

Molecular Formula C10H13N5O5S
Molecular Weight 315.306
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Approval Year

PubMed

PubMed

TitleDatePubMed
Activation of lymphocytes by a thiol-derivatized nucleoside: characterization of cellular parameters and responsive subpopulations.
1983 Feb
Derivatized guanine nucleosides: a new class of adjuvant for in vitro antibody responses.
1983 Jun
Mechanism of 8-mercaptoguanosine-mediated adjuvanticity: roles of clonal expansion and cellular recruitment.
1984 Dec
Regulation of B-lymphocyte proliferative responses by arachidonate metabolites: effects on membrane-directed versus intracellular activators.
1984 Sep
Restoration of humoral immunity in vitro in immunodeficient aging mice by C8-derivatized guanine ribonucleosides.
1985 Jun
Control of B cell proliferation: inhibition of responses to B cell mitogens induced by plasma cell tumors.
1985 May
Queuosine metabolism: possible relation to B-cell activation by C8 derivatives of guanosine.
1985 Sep
Distinct effects of dual substitution on inductive and differentiative activities of C8-substituted guanine ribonucleosides.
1986 Oct 15
"Numatrin," a nuclear matrix protein associated with induction of proliferation in B lymphocytes.
1987 Aug 15
Large, activated B cells are the primary B-cell target of 8-bromoguanosine and 8-mercaptoguanosine.
1987 May
Inducible Ig heavy chain switching in an IgM+ Ly-1 B cell line. Evidence for a state of switch commitment.
1988
5-Halo-6-phenyl pyrimidinones and 8-substituted guanosines: biological response modifiers with similar effects on B cells.
1988 Mar
8-Mercaptoguanosine overcomes unresponsiveness of human neonatal B cells to polysaccharide antigens.
1988 Oct 1
Role of salvage and phosphorylation in the immunostimulatory activity of C8-substituted guanine ribonucleosides.
1988 Oct 1
Patents
Substance Class Chemical
Created
by admin
on Fri Dec 15 18:14:39 GMT 2023
Edited
by admin
on Fri Dec 15 18:14:39 GMT 2023
Record UNII
B0T9FOW56N
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
8-THIOGUANOSINE
Common Name English
SQ 12760
Common Name English
GUANOSINE, 7,8-DIHYDRO-8-THIOXO-
Systematic Name English
NSC-79216
Code English
8-MERCAPTOGUANOSINE
Systematic Name English
GUANOSINE, 8-MERCAPTO-
Systematic Name English
Code System Code Type Description
EPA CompTox
DTXSID30948906
Created by admin on Fri Dec 15 18:14:39 GMT 2023 , Edited by admin on Fri Dec 15 18:14:39 GMT 2023
PRIMARY
CAS
686300-03-8
Created by admin on Fri Dec 15 18:14:39 GMT 2023 , Edited by admin on Fri Dec 15 18:14:39 GMT 2023
NON-SPECIFIC STEREOCHEMISTRY
CAS
26001-38-7
Created by admin on Fri Dec 15 18:14:39 GMT 2023 , Edited by admin on Fri Dec 15 18:14:39 GMT 2023
PRIMARY
PUBCHEM
135457302
Created by admin on Fri Dec 15 18:14:39 GMT 2023 , Edited by admin on Fri Dec 15 18:14:39 GMT 2023
PRIMARY
ECHA (EC/EINECS)
247-402-4
Created by admin on Fri Dec 15 18:14:39 GMT 2023 , Edited by admin on Fri Dec 15 18:14:39 GMT 2023
PRIMARY
NSC
79216
Created by admin on Fri Dec 15 18:14:39 GMT 2023 , Edited by admin on Fri Dec 15 18:14:39 GMT 2023
PRIMARY
FDA UNII
B0T9FOW56N
Created by admin on Fri Dec 15 18:14:39 GMT 2023 , Edited by admin on Fri Dec 15 18:14:39 GMT 2023
PRIMARY