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NITD 008 - ≥97%(HPLC), high purity , CAS No.1044589-82-3
Antiflaviviral; active against Zika, Dengue and Hepatitis C viruses
Basic Description
Synonyms
7H-Pyrrolo(2,3-d)pyrimidin-4-amine, 7-(2-c-ethynyl-beta-D-ribofuranosyl)- | LKI7T3WQ2E | 1044589-82-3 | UNII-LKI7T3WQ2E | (2R,3R,4R,5R)-2-(4-aminopyrrolo[2,3-d]pyrimidin-7-yl)-3-ethynyl-5-(hydroxymethyl)oxolane-3,4-diol | (2R,3R,4R,5R)-2-(4-AMINO-PYRROLO[
Specifications & Purity
≥97%(HPLC)
Biochemical and Physiological Mechanisms
Selective flavivirus inhibitor. Adenosine analog. Inhibits dengue virus (EC50= 0.64 μM), hepatitis C virus and cellular entry of Zika virus. Reduces increases of cytokines and NS1 and prevents death in dengue-infected mice. Activein vivo. Orally bioavaila
Storage Temp
Store at -20°C
Shipped In
Ice chest + Ice pads
This product requires cold chain shipping. Ground and other economy services are not available.
Taxonomic Classification
Kingdom
Organic compounds
Superclass
Nucleosides, nucleotides, and analogues
Class
Pyrrolopyrimidine nucleosides and nucleotides
Subclass
Not available
Intermediate Tree Nodes
Not available
Direct Parent
Pyrrolopyrimidine nucleosides and nucleotides
Alternative Parents
Glycosylamines Pentoses Pyrrolo[2,3-d]pyrimidines Aminopyrimidines and derivatives Ynones Substituted pyrroles Imidolactams Tertiary alcohols Heteroaromatic compounds Oxolanes Secondary alcohols Acetylides Oxacyclic compounds Azacyclic compounds Primary amines Hydrocarbon derivatives Primary alcohols
Molecular Framework
Aromatic heteropolycyclic compounds
Substituents
Pyrrolopyrimidine ribonucleoside - Glycosyl compound - N-glycosyl compound - Pentose monosaccharide - Pyrrolo[2,3-d]pyrimidine - Pyrrolopyrimidine - Aminopyrimidine - Monosaccharide - Substituted pyrrole - Ynone - Imidolactam - Pyrimidine - Heteroaromatic compound - Pyrrole - Tertiary alcohol - Oxolane - Secondary alcohol - Acetylide - Oxacycle - Azacycle - Organoheterocyclic compound - Amine - Organooxygen compound - Organonitrogen compound - Hydrocarbon derivative - Alcohol - Organic oxygen compound - Organic nitrogen compound - Primary alcohol - Primary amine - Aromatic heteropolycyclic compound
Description
This compound belongs to the class of organic compounds known as pyrrolopyrimidine nucleosides and nucleotides. These are nucleoside derivatives containing a ribose derivative which is n-glycosylated to a pyrrolopyrimidine. Also called deazapurine nucleosides, they are analogs of purine nucleosides with the N atom of the purine being replaced by a C atom at position 7.
External Descriptors
Not available
Data sources
1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.
Associated Targets(Human)
Associated Targets(non-human)
Mechanisms of Action
Mechanism of Action
Action Type
target ID
Target Name
Target Type
Target Organism
Binding Site Name
References
Names and Identifiers
IUPAC Name
(2R,3R,4R,5R)-2-(4-aminopyrrolo[2,3-d]pyrimidin-7-yl)-3-ethynyl-5-(hydroxymethyl)oxolane-3,4-diol
INCHI
InChI=1S/C13H14N4O4/c1-2-13(20)9(19)8(5-18)21-12(13)17-4-3-7-10(14)15-6-16-11(7)17/h1,3-4,6,8-9,12,18-20H,5H2,(H2,14,15,16)/t8-,9-,12-,13-/m1/s1
InChIKey
NKRAIOQPSBRMOV-NRMKKVEVSA-N
Smiles
C#CC1(C(C(OC1N2C=CC3=C(N=CN=C32)N)CO)O)O
Isomeric SMILES
C#C[C@]1([C@@H]([C@H](O[C@H]1N2C=CC3=C(N=CN=C32)N)CO)O)O
Molecular Weight
290.27
Reaxy-Rn
29225462
Reaxys-RN_link_address
https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=29225462&ln=
Certificates（CoA,COO,BSE/TSE and Analysis Chart)
Chemical and Physical Properties
Solubility
Solvent:DMSO, Max Conc. mg/mL: 5.81, Max Conc. mM: 20
Molecular Weight
290.270 g/mol
XLogP3
-1.400
Hydrogen Bond Donor Count
4
Hydrogen Bond Acceptor Count
7
Rotatable Bond Count
3
Exact Mass
290.102 Da
Monoisotopic Mass
290.102 Da
Topological Polar Surface Area
127.000 Ų
Heavy Atom Count
21
Formal Charge
0
Complexity
455.000
Isotope Atom Count
0
Defined Atom Stereocenter Count
4
Undefined Atom Stereocenter Count
0
Defined Bond Stereocenter Count
0
Undefined Bond Stereocenter Count
0
The total count of all stereochemical bonds
0
Covalently-Bonded Unit Count
1
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