Ribavirin monophosphate
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Basic information
- CAS
40925-28-8- Standard SMILES
NC(=O)c1ncn([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O)n1- InChIKey
SDWIOXKHTFOULX-AFCXAGJDSA-N- Molecular formula
- C8H13N4O8P
- Average molar mass
- 324.18 g/mol
- Monoisotopic mass
- 324.04710038
Names & identifiers
- Preferred name
- Ribavirin monophosphate
- IUPAC
- [(2R,3S,4R,5R)-5-(3-carbamoyl-1,2,4-triazol-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate
- English name
- ribavirin-5'-phosphate
- Molecular formula
- C8H13N4O8P
- Molecular weight
- 324.19
Names & synonyms
Ribavirin monophosphate40925-28-8Ribavirin-5'-phosphateRibavirin 5'-monophosphateRibavirin 5'-phosphate1-(5-O-Phosphono-beta-D-ribofuranosyl)-1H-1,2,4-triazole-3-carboxamideO9FVV27P11CHEBI:45490DTXSID20193928NSC-274937RefChem:930750DTXCID60116419
Show more names
Ribavirin 5'-monophosphate sodium saltResorcinol Impurity 38Ribavirin-5′,-monophosphate1H-1,2,4-Triazole-3-carboxamide, 1-(5-O-phosphono-β-D-ribofuranosyl)-[(2R,3S,4R,5R)-5-(3-carbamoyl-1,2,4-triazol-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate((2R,3S,4R,5R)-5-(3-carbamoyl-1H-1,2,4-triazol-1-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl dihydrogen phosphate
1 beta-D-ribofuranosyl-1,2,4-triazole-3-carboxamide-5'-phosphate(((2R,3S,4R,5R)-5-(3-carbamoyl-1H-1,2,4-triazol-1-yl)-3,4-dihydroxyoxolan-2-yl)methoxy)phosphonic acidVirazole 5'-phosphateICN 38471beta-D-Ribofuranosyl-1,2,4-triazole-3-carboxamide-5'-phosphate1H-1,2,4-Triazole-3-carboxamide, 1-(5-O-phosphono-.beta.-D-ribofuranosyl)-RVPUNII-O9FVV27P11
Database identifiers
- CAS
40925-28-8- PubChem CID
- 100252
- DTXSID
DTXSID20193928- ChEMBL
CHEMBL1235764- ChEBI
CHEBI:45490- UNII
- O9FVV27P11
- Nikkaji
- J485.213C
Properties
Computed structural propertiesFilling in
- XLogP
- -3.5
- Topological polar surface area
- 190 Ų
- Hydrogen bond donors
- 5
- Hydrogen bond acceptors
- 10
- Rotatable bonds
- 5
- Heavy atoms
- 21
- Formal charge
- 0
- Complexity
- 446
Physicochemical properties
- Boiling point
- 767.3 · 767.3±70.0 °C(Predicted)
- Density
- 2.33 · 2.33±0.1 g/cm3(Predicted)
- pka
- 1.86 · 1.86±0.10(Predicted)
- FDA UNII
- 9 FVV27P11 · O9FVV27P11
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly.
Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.
Applications
UsesRibavirin Monophosphate, is a metabolite of Ribavirin (R414475), a urine nucleoside analog; inhibits inosine monophosphate dehydrogenase (IMPDH). Used as an antiviral agent.
Additional notes
DefinitionChEBI: Ribavirin 5'-monophosphate is a 1-ribosyltriazole that is ribavirin in which the hydroxy group at the 5'-position is replaced by a phosphonooxy group. It is the active metabolite of the antiviral agent ribavirin. It has a role as a human blood serum metabolite, a drug metabolite, an antiviral agent and an EC 1.1.1.205 (IMP dehydrogenase) inhibitor. It is a 1-ribosyltriazole, a ribose monophosphate, an aromatic amide, a monocarboxylic acid amide and a primary carboxamide. It is functionally related to a ribavirin. It is a conjugate acid of a ribavirin 5'-monophosphate(2-).
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