3-beta-D-Ribofuranosyl-1H-pyrrole-2,5-dione
Basic information
- CAS
16755-07-0- Standard SMILES
O=C1C=C([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C(=O)N1- InChIKey
FFLUMYXAPXARJP-JBBNEOJLSA-N- Molecular formula
- C9H11NO6
- Average molar mass
- 229.19 g/mol
- Monoisotopic mass
- 229.05863707
Overview
Showdomycin is a C-glycosyl compound.
Names & identifiers
- Preferred name
- 3-beta-D-Ribofuranosyl-1H-pyrrole-2,5-dione
- IUPAC
- 3-[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrrole-2,5-dione
- English name
- 3-beta-D-Ribofuranosylpyrrole-2,5-dione
- Molecular formula
- C9H11NO6
- Molecular weight
- 229.19
Names & synonyms
Showdomycin16755-07-02-beta-D-Ribofuranosylmaleimide3-beta-D-Ribofuranosyl-1H-pyrrole-2,5-dioneE1V8315QHYDTXSID001043162NSC-930473-[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrrole-2,5-dione3-((2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl)pyrrole-2,5-dioneRefChem:182762DTXCID601340518D-Showdomycin
Show more names
d-(+)-showdomycin2-β-D-Ribofuranosylmaleimide2-β-D-Ribofuranosyl-maleimide2-beta-d-ribofuranosyl-maleimid3-β-D-Ribofuranosyl-1H-pyrrole-2,5-dione3-beta-d-ribofuranosyl-1h-pyrrole-5-dione
2-?-D-Ribofuranosyl-maleimide3-BETA-D-RIBOFURANOSYLPYRROLE-2,5-DIONE1H-Pyrrole-2,5-dione, 3-.beta.-D-ribofuranosyl-NSC 93047BRN 0538225UNII-E1V8315QHYMALEIMIDE, 2-beta-D-RIBOFURANOSYL-SHOWDOMYCIN [MI]
Database identifiers
Properties
Computed structural properties
- XLogP
- -2.5
- Topological polar surface area
- 116 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 2
- Heavy atoms
- 16
- Formal charge
- 0
- Complexity
- 365
Experimental & physicochemical properties
SpringerMaterials PropertiesCrystal structure
Physicochemical properties
- Melting point
- 153 · 153-154°
- alpha
- 22.5 · D22.5 +49.9° (H2O)
- Boiling point
- 371.08 °C · 371.08°C (rough estimate)
- Density
- 1.4278 · 1.4278 (rough estimate)
- refractive index
- 1.527 · 1.5270 (estimate)
- pka
- 8.08 · 8.08±0.40(Predicted)
- FDA UNII
- 1 V8315QHY · E1V8315QHY
- Toxicity
- 50 in · LD50 in mice (mg/kg): 25 i.p.; 18 s.c.; 110 i.v. (Nishimura)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- Toxicity
- LD50 in mice (mg/kg): 25 i.p.; 18 s.c.; 110 i.v. (Nishimura)
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Chemical substances, produced by microorganisms, inhibiting or preventing the proliferation of neoplasms.
Chemical agents that react with SH groups. This is a chemically diverse group that is used for a variety of purposes. Among these are enzyme inhibition, enzyme reactivation or protection, and labelling.
Applications
DescriptionShowdomycin, isolated from Streptomyces showdoensis, is very active against Streptococcus hemolyticus. It is moderately active against other gram-positive and gram-negative bacteria and also effective against Ehrlich ascites tumor in mice and HeLa cells . Oxazinomycin belongs to this class of nucleosides .
Uses2-β-D-Ribofuranosyl-maleimide is a useful chemical reagent which has anti bacterial properties.
Related reactions
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Compound notes
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