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2',3'-cGAMP

CAT: 0957-E5781-1mgSize: 1 mgDry Ice: NoHazardous: No
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CAT#:0957-E5781-1mgSize:1 mg
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CAS Number
1441190-66-4
Synonyms
2'-3'-cyclic GMP-AMP
Target
IFN
Applications
Immunology & Inflammation
Molecular Formula
C20H24N10O13P2
Additionnal Information
2',3'-cGAMP (2'-3'-cyclic GMP-AMP) is an endogenous cyclic GMP-AMP produced in mammalian cells in response to cytoplasmic DNA. It binds STING with high affinity Kd of 3.79 nM and is a potent inducer of interferon-β (IFNβ) .

Chemical Information

2'3'-Cyclic guanosine monophosphate-adenosine monophosphate

2'-3'-cGAMP is a cyclic purine dinucleotide that consists of AMP and GMP units cyclised via 3',5'- and 2',5'-linkages respectively. It is a cyclic purine dinucleotide, a guanyl ribonucleotide and an adenyl ribonucleotide. It is functionally related to a Gp[2'-5']Ap[3']. It is a conjugate acid of a 2'-3'-cGAMP(2-).

CAS Number1441190-66-4
PubChem CID135564529
IUPAC Name2-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-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one
Molecular FormulaC20H24N10O13P2
Molecular Weight674.4
XLogP-5.9
Topological Polar Surface Area325
Hydrogen Bond Donor Count7
Hydrogen Bond Acceptor Count19
Rotatable Bond Count2
Heavy Atom Count45
Formal Charge0
Complexity1300
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
InChI
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
InChIKey
XRILCFTWUCUKJR-INFSMZHSSA-N
Chemical Structure
2D Structure
2D structure of 2'3'-Cyclic guanosine monophosphate-adenosine monophosphate
CAS: 1441190-66-4
CID: 135564529
Formula: C20H24N10O13P2
MW: 674.4
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight674.4
XLogP3-5.9
Hydrogen Bond Donor Count7
Hydrogen Bond Acceptor Count19
Rotatable Bond Count2
Exact Mass674.09995485
Monoisotopic Mass674.09995485
Topological Polar Surface Area325 Ų
Heavy Atom Count45
Formal Charge0
Complexity1300
Isotope Atom Count0
Defined Atom Stereocenter Count8
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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