Metabolomics Structure Database

MDLMOL SDF CSV TSV

MW REGNO:	65784
Common Name:	c-GMP-AMP
Systematic Name:	2-amino-9-[(2R,3R,3aS,7aR,9R,10R,10aS,14aR)-9-(6-amino-9H-purin-9-yl)-3,5,10,12-tetrahydroxy-5,12-dioxidooctahydro-2H,7H-difuro[3,2-d:3',2'-j][1,3,7,9,2,8]tetraoxadiphosphacyclododecin-2-yl]-1,9-dihydro-6H-purin-6-one
Synonyms:	3',5'-cyclic GMP-AMP; cyclic GMP-AMP [PubChem Synonyms]
Exact Mass:	674.1000 (neutral)    Calculate m/z: (Choose adduct) [M+H]+ [M+H-H2O]+ [M.]+ [M+2H]2+ [M+3H]3+ [M+4H]4+ [M+K]+ [M+2K]2+ [M-H+2K]+ [M+Na]+ [M+2Na]2+ [M-H+2Na]+ [M+Li]+ [M+2Li]2+ [M+NH4]+ [M-H]- [M-2H]2- [M-3H]3- [M-4H]4- [M+Cl]- [M+OAc]- [M+HCOO]- M(neutral)
Formula:	C20H24N10O13P2
InChIKey:	RFCBNSCSPXMEBK-INFSMZHSSA-N
ClassyFire superclass:	Nucleosides, nucleotides, and analogues [C0000289]
ClassyFire class:	(3'->5')-dinucleotides [C0003796]
ClassyFire subclass:	(3'->5')-cyclic dinucleotides and analogues
ClassyFire direct parent:	(3'-u003e5')-cyclic dinucleotides and analogues
SMILES:	C1[C@@H]2[C@H]([C@H]([C@H](n3cnc4c(N)ncnc34)O2)O)OP(=O)(O)OC[C@@H]2[C@H]([C@H]([C@H](n3cnc4c3nc(N)[nH]c4=O)O2)O)OP(=O)(O)O1
Studies:	-

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All Database Links Calculated Properties Human Pathways

External database links:

PubChem CID:	135471108
CHEBI ID:	71580
HMDB ID:	HMDB0060465

Calculated physicochemical properties (?):

Heavy Atoms:	45
Rings:	7
Aromatic Rings:	4
Rotatable Bonds:	2
van der Waals Molecular volume:	467.25 Å3 molecule-1
Toplogical Polar Sufrace Area:	342.07 Å2 molecule-1
Hydrogen Bond Donors:	7
Hydrogen Bond Acceptors:	20
logP:	1.03
Molar Refractivity:	147.25
Fraction sp3 Carbons:	0.50
sp3 Carbons:	10

Human Pathway links:

REACTOME pathways containing this metabolite

References

LIPID MAPS classification: "Update of the LIPID MAPS comprehensive classification system for lipids", Fahy E, Subramaniam S, Murphy RC, Nishijima M, Raetz CR, Shimizu T, Spener F, van Meer G, Wakelam MJ, and Dennis EA, J. Lipid Res. (2009) 50: S9-S14. DOI: 10.1194/jlr.R800095-JLR200
ClassyFire classification: "ClassyFire: automated chemical classification with a comprehensive, computable taxonomy", 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, J. Cheminformatics (2016) 8:61. DOI: 10.1186/s13321-016-0174-y