Summary

Full nameguanosine-5'-monophosphate
IUPAC name[(2R,3S,4R,5R)-5-(2-amino-6-oxo-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate
Short namepG
MODOMICS code551G
Synonyms
[(2R,3S,4R,5R)-5-(2-amino-6-oxo-3H-purin-9-yl)-3,4-dihydroxy-2-oxolanyl]methyl phosphate
[(2R,3S,4R,5R)-5-(2-amino-6-oxo-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate
[(2R,3S,4R,5R)-5-(2-azanyl-6-oxidanylidene-3H-purin-9-yl)-3,4-bis(oxidanyl)oxolan-2-yl]methyl phosphate
5'-Guanylic acid
5'-O-phosphonatoguanosine
85-32-5
A841293
AC1LXT7S
CHEBI:58115
CID1807035
CJ-07810
GMP
GMP dianion
GMP(2-)
Guanosine 5'-monophosphate
guanosine 5'-monophosphate(2-)
Guanosine 5'-phosphate
guanosine 5'-phosphate dianion
guanosine 5'-phosphate(2-)
guanosine monophosphate
guanosine phosphate
guanosine-5'-monophosphate
guanylate
guanylic acid
LS-190270
Q27125193

Nature of the modified residueNatural
Residue unique ID235
Found in RNAYes
Related nucleosides38
RCSB ligands

5GP


Chemical information

Sum formulaC10H12N5O8P
Type of moietynucleotide
Degeneracynot aplicable
SMILESNc1nc2c(nc[n]2[C@@H]2O[C@H](COP(=O)([O-])[O-])[C@@H](O)[C@H]2O)c(=O)[nH]1
logP-1.1121
TPSA221.51
Number of atoms24
Number of Hydrogen Bond Acceptors 1 (HBA1)9
Number of Hydrogen Bond Acceptors 2 (HBA2)12
Number of Hydrogen Bond Donors (HBD)4
InChIInChI=1S/C10H14N5O8P/c11-10-13-7-4(8(18)14-10)12-2-15(7)9-6(17)5(16)3(23-9)1-22-24(19,20)21/h2-3,5-6,9,16-17H,1H2,(H2,19,20,21)(H3,11,13,14,18)/p-2/t3-,5-,6-,9-/m1/s1
InChIKeyRQFCJASXJCIDSX-UUOKFMHZSA-L
Search the molecule in external databases ChEMBL  ChemAgora  ChEBI  PubChem Compound Database  Ligand Expo  ChemSpider  WIPO 
PubChem CID
PubChem SIDs

* Chemical properties calculated with Open Babel - O'Boyle et al. Open Babel: An open chemical toolbox. J Cheminform 3, 33 (2011) (link)


Download Structures

2D   .png .mol .mol2 .sdf .pdb .smi
3D   .mol .mol2 .sdf .pdb

Tautomers

Tautomers SMILES
N=c1[nH]c2c(ncn2C3OC(COP(=O)([O-])[O-])C(O)C3O)c(=O)[nH]1 tautomer #0
Nc1nc2c(ncn2C3OC(COP(=O)([O-])[O-])C(O)C3O)c(O)n1 tautomer #1
Nc1[nH]c2c(ncn2C3OC(COP(=O)([O-])[O-])C(O)C3O)c(=O)n1 tautomer #2
Nc1nc2c(ncn2C3OC(COP(=O)([O-])[O-])C(O)C3O)c(=O)[nH]1 tautomer #3
N=c1nc2c(ncn2C3OC(COP(=O)([O-])[O-])C(O)C3O)c(O)[nH]1 tautomer #4
N=C1N=C2C(N=CN2C3OC(COP(=O)([O-])[O-])C(O)C3O)C(=O)N1 tautomer #5
Nc1nc2c(ncn2C3OC(COP(=O)([O-])[O-])C(O)C3O)c(O)n1 tautomer #6
NC=1N=C2C(N=CN2C3OC(COP(=O)([O-])[O-])C(O)C3O)C(=O)N1 tautomer #7
N=c1[nH]c2c(ncn2C3OC(COP(=O)([O-])[O-])C(O)C3O)c(O)n1 tautomer #8
N=C1N=C2C(N=CN2C3OC(COP(=O)([O-])[O-])C(O)C3O)C(O)=N1 tautomer #9

Tautomer image Show Image

Predicted CYP Metabolic Sites

CYP3A4 CYP2D6 CYP2C9
pG pG pG

* CYP Metabolic sites predicted with SMARTCyp. SMARTCyp is a method for prediction of which sites in a molecule that are most liable to metabolism by Cytochrome P450. It has been shown to be applicable to metabolism by the isoforms 1A2, 2A6, 2B6, 2C8, 2C19, 2E1, and 3A4 (CYP3A4), and specific models for the isoform 2C9 (CYP2C9) and isoform 2D6 (CYP2D6). CYP3A4, CYP2D6, and CYP2C9 are the three of the most important enzymes in drug metabolism since they are involved in the metabolism of more than half of the drugs used today. The three top-ranked atoms are highlighted. See: SmartCYP and SmartCYP - background; Patrik Rydberg, David E. Gloriam, Lars Olsen, The SMARTCyp cytochrome P450 metabolism prediction server, Bioinformatics, Volume 26, Issue 23, 1 December 2010, Pages 2988–2989 (link)


LC-MS Information

Monoisotopic massNone
Average mass361.205
[M+H]+ not available
Product ions not available
Normalized LC elution time * not available
LC elution order/characteristics not available

* normalized to guanosine (G), measured with a RP C-18 column with acetonitrile/ammonium acetate as mobile phase.

Last modification of this entry: Sept. 29, 2021


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