Ketcher 11051516402D 1   1.00000     0.00000     0

 17 18  0     1  0            999 V2000
   11.9718  -11.4054    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7809  -11.9932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4718  -12.9444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4717  -12.9444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1626  -11.9932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1428  -10.9949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7714  -10.9941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0597  -13.7536    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8838  -13.7536    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2701  -10.5062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9609  -10.4082    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   13.5790  -10.4042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2675   -9.4563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2676   -9.4537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8534   -8.6431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8483   -8.7451    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.4443   -7.7304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0     0  0
  5  1  1  0     0  0
  2  7  1  1     0  0
  2  3  1  0     0  0
  3  8  1  6     0  0
  3  4  1  0     0  0
  4  9  1  6     0  0
  4  5  1  0     0  0
  5  6  1  1     0  0
 10  6  1  0     0  0
 11  7  1  0     0  0
 12  7  2  0     0  0
 13 11  1  0     0  0
 14 12  1  0     0  0
 14 13  2  0     0  0
 14 15  1  0     0  0
 15 16  1  0     0  0
 15 17  2  0     0  0
M  END
> <ID>
CHEBI:90239

> <NAME>
tiazofurine

> <DEFINITION>
A C-glycosyl compound that is 1,3-thiazole-4-carboxamide in which the hydrogen at position 2 has been replaced by a β-D-ribofuranosyl group. It is metabolised to thiazole-4-carboxamide adenine dinucleotide (TAD), a selective inhibitor of inosine monophosphate dehydrogenase (IMP dehydrogenase).

> <STAR>
3

> <SYNONYM>
tiazofurin; TCAR; riboxamide; CI-909; 2-beta-D-ribofuranosyl-4-thiazolecarboxamide; 2-(beta-D-ribofuranosyl)-4-thiazolecarboxamide

> <IUPAC_NAME>
(1R)-1,4-anhydro-1-(4-carbamoyl-1,3-thiazol-2-yl)-D-ribitol

> <INN>
tiazofurinum; tiazofurine; tiazofurine; tiazofurina

> <FORMULA>
C9H12N2O5S

> <MASS>
260.268

> <MONOISOTOPIC_MASS>
260.04669

> <CHARGE>
0

> <SMILES>
O1[C@@H](C=2SC=C(N2)C(N)=O)[C@H](O)[C@H](O)[C@H]1CO

> <INCHI>
InChI=1S/C9H12N2O5S/c10-8(15)3-2-17-9(11-3)7-6(14)5(13)4(1-12)16-7/h2,4-7,12-14H,1H2,(H2,10,15)/t4-,5-,6-,7-/m1/s1

> <INCHIKEY>
FVRDYQYEVDDKCR-DBRKOABJSA-N

> <CAS_REGISTRY_NUMBER>
60084-10-8

> <REAXYS_REGISTRY_NUMBER>
1084555

> <CHEMIDPLUS>
60084-10-8

> <KEGG_DRUG_ACCESSION>
D06130

> <PDBECHEM_ACCESSION>
TIZ

> <WIKIPEDIA_ACCESSION>
Tiazofurin

> <PUBMED_CITATION>
11249583; 23764899; 2712550; 8667040

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