Common NameDgmp
Description2'-Deoxyguanosine 5'-monophosphate, also known as deoxyguanylic acid or 2'-deoxy-GMP, belongs to the class of organic compounds known as purine 2'-deoxyribonucleoside monophosphates. These are purine nucleotides with monophosphate group linked to the ribose moiety lacking a hydroxyl group at position 2. 2'-Deoxyguanosine 5'-monophosphate is a purine 2'-deoxyribonucleoside 5'-monophosphate having guanine as the nucleobase. It exists in all living species, ranging from bacteria to humans. Within humans, 2'-deoxyguanosine 5'-monophosphate participates in a number of enzymatic reactions. In particular, 2'-deoxyguanosine 5'-monophosphate can be converted into dGDP which is mediated by the enzyme guanylate kinase. In addition, 2'-deoxyguanosine 5'-monophosphate can be converted into deoxyguanosine through its interaction with the enzyme cytosolic purine 5'-nucleotidase. In humans, 2'-deoxyguanosine 5'-monophosphate is involved in the metabolic disorder called the gout or kelley-seegmiller syndrome pathway.
Structure
Molecular FormulaC10H14N5O7P
Average Mass347.22120
Monoisotopic Mass347.06308
IUPAC Name{[(2R,3S,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy}phosphonic acid
Traditional Name[(2r,3s,5r)-5-(2-amino-6-oxo-1h-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxyphosphonic acid
CAS Registry Number0902-04-05
SMILESNc1nc2c(ncn2[C@H]2C[C@H](O)[C@@H](COP(=O)([O-])[O-])O2)c(=O)[nH]1
InChI IdentifierInChI=1S/C10H14N5O7P/c11-10-13-8-7(9(17)14-10)12-3-15(8)6-1-4(16)5(22-6)2-21-23(18,19)20/h3-6,16H,1-2H2,(H2,18,19,20)(H3,11,13,14,17)/t4-,5+,6+/m0/s1
InChI KeyLTFMZDNNPPEQNG-KVQBGUIXSA-N
CHEBI IDCHEBI:57673
HMDB IDHMDB0001044
Pathways
NameSMPDB/PathBank
Purine metabolism
Adenosine Deaminase Deficiency
Adenylosuccinate Lyase Deficiency
AICA-Ribosiduria
Molybdenum Cofactor Deficiency
Purine Nucleoside Phosphorylase Deficiency
Xanthine Dehydrogenase Deficiency (Xanthinuria)
Lesch-Nyhan Syndrome (LNS)
Gout or Kelley-Seegmiller Syndrome
Azathioprine Action Pathway
Mercaptopurine Action Pathway
Thioguanine Action Pathway
Xanthinuria type I
Xanthinuria type II
Adenine phosphoribosyltransferase deficiency (APRT)
Mitochondrial DNA depletion syndrome
Myoadenylate deaminase deficiency
StateSolid
Water Solubility2.70e+00 g/l
logP-1.87
logS-2.11
pKa (Strongest Acidic)1.06
pKa (Strongest Basic)1.74
Hydrogen Acceptor Count9
Hydrogen Donor Count5
Polar Surface Area181.52 Ų
Rotatable Bond Count4
Physiological Charge-2
Formal Charge0
Refractivity73.98 m³·mol⁻¹
Polarizability30.02

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