2',3'-cGAMP - ≥99% , CAS No.1441190-66-4

CAS: 1441190-66-4 Cat. No.: C1434818 Molecular Weight: 674.41 (free acid basis)

GRADE & PURITY ≥99%

Storage

Store at -20°C,Desiccated

Shipped In

Ice chest + Ice pads

Overview

2',3'-cGAMP (2'-3'-cyclic GMP-AMP) is a endogenous cGAMP in mammalian cells. 2',3'-cGAMP binds to STING with a high affinity and is a potent inducer of interferon-β (IFNβ). 2',3'-cGAMP is produced in mammalian cells in response to DNA in the cytoplasm.

Specifications

Specifications & Purity

≥99%

Storage

Store at -20°C, Desiccated

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Action Type

ACTIVATOR

Purity

≥99%

Names and Identifiers

• Canonical Smiles: C1C2C(C(C(O2)N3C=NC4=C3N=C(NC4=O)N)OP(=O)(OCC5C(C(C(O5)N6C=NC7=C(N=CN=C76)N)O)OP(=O)(O1)O)O)O
• IUPAC Name: 2-amino-9-[(1R,6R,8R,9R,10S,15R,17R,18R)-8-(6-aminopurin-9-yl)-3,9,12,18-tetrahydroxy-3,12-dioxo-2,4,7,11,13,16-hexaoxa-3λ5,12λ5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one
• InChIKey: XRILCFTWUCUKJR-INFSMZHSSA-N
• INCHI: 1S/C20H24N10O13P2/c21-14-8-15(24-3-23-14)29(4-25-8)18-11(32)12-7(41-18)2-39-45(36,37)43-13-10(31)6(1-38-44(34,35)42-12)40-19(13)30-5-26-9-16(30)27-20(22)28-17(9)33/h3-7,10-13,18-19,31-32H,1-2H2,(H,34,35)(H,36,37)(H2,21,23,24)(H3,22,27,28,33)/t6-,7-,10-,11-,12-,13-,18-,19-/m1/s1
• Isomeric SMILES: C1[C@@H]2[C@H]([C@H]([C@@H](O2)N3C=NC4=C3N=C(NC4=O)N)OP(=O)(OC[C@@H]5[C@H]([C@H]([C@@H](O5)N6C=NC7=C(N=CN=C76)N)O)OP(=O)(O1)O)O)O
• Alternate CAS: 1441190-66-4
• MeSH Entry Terms: cGAMP;cyclic GMP-AMP;cyclic guanosine monophosphate-adenosine monophosphate
• Molecular Weight: 674.41 (free acid basis)
• Reaxy-Rn: 35304092
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=35304092&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Nucleosides, nucleotides, and analogues
    • Class Purine nucleotides
      • Subclass Purine ribonucleotides
        • Level5 Purine ribonucleoside bisphosphates
          • Level6 Purine ribonucleoside 3',5'-bisphosphates

• Kingdom: Organic compounds
• Superclass: Nucleosides, nucleotides, and analogues
• Class: Purine nucleotides
• Subclass: Purine ribonucleotides
• Intermediate Tree Nodes: Purine ribonucleoside bisphosphates
• Direct Parent: Purine ribonucleoside 3',5'-bisphosphates
• Alternative Parents: Purine ribonucleoside 2',5'-bisphosphates Pentose phosphates Nucleoside and nucleotide analogues Glycosylamines Hypoxanthines Monosaccharide phosphates 6-oxopurines 6-aminopurines Aminopyrimidines and derivatives Pyrimidones Organic phosphoric acids and derivatives N-substituted imidazoles Imidolactams Tetrahydrofurans Heteroaromatic compounds Vinylogous amides Secondary alcohols Oxacyclic compounds Azacyclic compounds Polyols Hydrocarbon derivatives Organic oxides Organopnictogen compounds Primary amines
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Purine ribonucleoside 2',5'-bisphosphate - Purine ribonucleoside 3',5'-bisphosphate - Pentose-5-phosphate - Pentose phosphate - Glycosyl compound - N-glycosyl compound - 6-aminopurine - 6-oxopurine - Hypoxanthine - Monosaccharide phosphate - Imidazopyrimidine - Purine - Aminopyrimidine - Pyrimidone - Pyrimidine - Organic phosphoric acid derivative - Imidolactam - N-substituted imidazole - Monosaccharide - Azole - Heteroaromatic compound - Imidazole - Vinylogous amide - Tetrahydrofuran - Secondary alcohol - Organoheterocyclic compound - Azacycle - Oxacycle - Polyol - Organopnictogen compound - Amine - Alcohol - Organic oxygen compound - Hydrocarbon derivative - Organic oxide - Organic nitrogen compound - Organonitrogen compound - Organooxygen compound - Primary amine - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as purine ribonucleoside 3',5'-bisphosphates. These are purine ribobucleotides with one phosphate group attached to 3' and 5' hydroxyl groups of the ribose moiety.
• External Descriptors: adenyl ribonucleotide - guanyl ribonucleotide - cyclic purine dinucleotide

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.

DOI: 10.1186/s13321-016-0174-y