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2-5A

CAT: 0804-HY-173189Size: 1 EachDry Ice: NoHazardous: No
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Description
2-5A is a 5'-triphosphorylated (2',5') oligoadenylate. 2-5A is an immunotransmitter that fuels RNase L immunity. 2-5A degrades viral mRNA and inhibits protein synthesis by binding to RNase L and activating its endoribonuclease activity. 2-5A can be used in RSV and cancer research[1][2][3][4].
CAS Number
65954-93-0
Product Name Alternative
2′,5′-ApApA; 2′,5′-trioligoadenylate; 5'-O-Triphosphoryladenylyl- (2'→5') -adenylyl- (2'→5') -adenosine
UNSPSC
12352005
Target
DNA/RNA Synthesis; RSV
Related Pathways
Anti-infection; Cell Cycle/DNA Damage
Applications
COVID-19-anti-virus
Field of Research
Cancer; Infection; Inflammation/Immunology
Smiles
NC1=NC=NC2=C1N=CN2[C@H]3[C@H](OP(O)(OC[C@@H](O[C@H]([C@@H]4OP(O)(OC[C@@H](O[C@H]([C@@H]5O)N6C=NC7=C6N=CN=C7N)[C@H]5O)=O)N8C=NC9=C8N=CN=C9N)[C@H]4O)=O)[C@H](O)[C@@H](COP(OP(OP(O)(O)=O)(O)=O)(O)=O)O3
Molecular Formula
C30H40N15O25P5
Molecular Weight
1165.59
References & Citations
[1]Kalinichenko EN, et al. 3'-Fluoro-3'-deoxy analogs of 2-5A 5'-monophosphate: binding to 2-5A-dependent endoribonuclease and susceptibility to (2'-5') phosphodiesterase degradation. Biochem Biophys Res Commun. 1990 Feb 28;167 (1) :20-6.|[2]Barnard DL, Sidwell RW, Xiao W, Player MR, Adah SA, Torrence PF. 2-5A-DNA conjugate inhibition of respiratory syncytial virus replication: effects of oligonucleotide structure modifications and RNA target site selection. Antiviral Res. 1999 Apr;41 (3) :119-34. |[3]Wang S, Li L. 2-5A is an immunotransmitter that fuels RNase L immunity. Immunity. 2025 Apr 8;58 (4) :770-772. |[4]Huai W, et al. OAS cross-activates RNase L intercellularly through cell-to-cell transfer of 2-5A to spread innate immunity. Immunity. 2025 Apr 8;58 (4) :797-810.e6. doi: 10.1016/j.immuni.2025.01.016. Epub 2025 Feb 25.
Shipping Conditions
Room temperature
Scientific Category
Oligonucleotides
Clinical Information
No Development Reported

Chemical Information

Adenosine triphosphate adenosine monophosphate adenosine monophosphate

see also 2',5'-oligoadenylate

CAS Number65954-93-0
PubChem CID125229
IUPAC Name[[(2R,3R,5R)-5-(6-aminopurin-9-yl)-4-[[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-4-[[(2R,3S,4R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate
Molecular FormulaC30H40N15O25P5
Molecular Weight1165.6
XLogP-10.9
Topological Polar Surface Area589
Hydrogen Bond Donor Count13
Hydrogen Bond Acceptor Count37
Rotatable Bond Count20
Heavy Atom Count75
Formal Charge0
Complexity2270
SMILES
C1=NC(=C2C(=N1)N(C=N2)[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(O)OC4[C@@H]([C@H](O[C@H]4N5C=NC6=C(N=CN=C65)N)COP(=O)(O)OP(=O)(O)OP(=O)(O)O)O)O)OP(=O)(O)OC[C@@H]7[C@H]([C@H](C(O7)N8C=NC9=C(N=CN=C98)N)O)O)N
InChI
InChI=1S/C30H40N15O25P5/c31-22-13-25(37-4-34-22)43(7-40-13)28-19(49)16(46)10(64-28)1-61-72(53,54)67-20-17(47)11(65-29(20)44-8-41-14-23(32)35-5-38-26(14)44)2-62-73(55,56)68-21-18(48)12(3-63-74(57,58)70-75(59,60)69-71(50,51)52)66-30(21)45-9-42-15-24(33)36-6-39-27(15)45/h4-12,16-21,28-30,46-49H,1-3H2,(H,53,54)(H,55,56)(H,57,58)(H,59,60)(H2,31,34,37)(H2,32,35,38)(H2,33,36,39)(H2,50,51,52)/t10-,11-,12-,16-,17-,18-,19-,20-,21?,28?,29-,30-/m1/s1
InChIKey
RTAGLZBJCCVJET-MFSXEPBNSA-N
Chemical Structure
2D Structure
2D structure of Adenosine triphosphate adenosine monophosphate adenosine monophosphate
CAS: 65954-93-0
CID: 125229
Formula: C30H40N15O25P5
MW: 1165.6
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight1165.6
XLogP3-10.9
Hydrogen Bond Donor Count13
Hydrogen Bond Acceptor Count37
Rotatable Bond Count20
Exact Mass1165.10078681
Monoisotopic Mass1165.10078681
Topological Polar Surface Area589 Ų
Heavy Atom Count75
Formal Charge0
Complexity2270
Isotope Atom Count0
Defined Atom Stereocenter Count10
Undefined Atom Stereocenter Count2
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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