Metabolomics Structure Database

MDLMOL SDF CSV TSV

MW REGNO:	52516
Common Name:	c-di-GMP
Systematic Name:	2-amino-9-[(1S,6R,8R,9R,10S,15R,17R,18R)-17-(2-amino-6-oxo-1H-purin-9-yl)-3,9,12,18-tetrahydroxy-3,12-dioxo-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.3.0.06,10]octadecan-8-yl]-1H-purin-6-one
Synonyms:	3',5'-Cyclic diguanylic acid [PubChem Synonyms]
Exact Mass:	690.0949 (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:	C20H24N10O14P2
InChIKey:	PKFDLKSEZWEFGL-MHARETSRSA-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](n3cnc4c3nc(N)[nH]c4=O)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:	135440063
CHEBI ID:	49537

Calculated physicochemical properties (?):

Heavy Atoms:	46
Rings:	7
Aromatic Rings:	4
Rotatable Bonds:	2
van der Waals Molecular volume:	476.04 Å3 molecule-1
Toplogical Polar Sufrace Area:	362.04 Å2 molecule-1
Hydrogen Bond Donors:	8
Hydrogen Bond Acceptors:	20
logP:	1.07
Molar Refractivity:	150.11
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