Showing Metabocard for GMP (BASm0003206)

Common NameGmp
DescriptionGuanosine monophosphate (GMP), also known as 5′-guanidylic acid or guanylic acid (conjugate base guanylate), is a nucleotide that is used as a monomer in RNA. It is an ester of phosphoric acid with the nucleoside guanosine. GMP consists of the phosphate group, the pentose sugar ribose, and the nucleobase guanine; hence it is a ribonucleoside monophosphate. Guanosine monophosphate is commercially produced by microbial fermentation. Guanosine monophosphate, also known as guanylic acid or 5'-GMP, belongs to the class of organic compounds known as purine ribonucleoside monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached. A guanine nucleotide containing one phosphate group esterified to the sugar moiety and found widely in nature. Guanosine monophosphate exists in all living species, ranging from bacteria to humans. Within humans, guanosine monophosphate participates in a number of enzymatic reactions. In particular, guanosine triphosphate and guanosine monophosphate can be biosynthesized from diguanosine tetraphosphate through its interaction with the enzyme bis(5'-nucleosyl)-tetraphosphatase [asymmetrical]. In addition, guanosine monophosphate can be biosynthesized from guanosine diphosphate; which is mediated by the enzyme ectonucleoside triphosphate diphosphohydrolase 5. In humans, guanosine monophosphate is involved in the metabolic disorder called the lesch-nyhan syndrome (lns) pathway. Outside of the human body, guanosine monophosphate has been detected, but not quantified in several different foods, such as common cabbages, tea, winter squash, spearmints, and sugar apples.
Structure
Molecular FormulaC10H14N5O8P
Average Mass363.22060
Monoisotopic Mass363.05800
IUPAC Name{[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
Traditional Name[(2r,3s,4r,5r)-5-(2-amino-6-oxo-1h-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxyphosphonic acid
CAS Registry Number85-32-5
SMILESNc1nc2c(ncn2[C@@H]2O[C@H](COP(=O)([O-])[O-])[C@@H](O)[C@H]2O)c(=O)[nH]1
InChI IdentifierInChI=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)/t3-,5-,6-,9-/m1/s1
InChI KeyRQFCJASXJCIDSX-UUOKFMHZSA-N
CHEBI IDCHEBI:58115
HMDB IDHMDB0001397
Pathways
NameSMPDB/PathBank
Purine metabolism
Transcription/Translation
Glutamate Metabolism
2-Hydroxyglutric Aciduria (D And L Form)
Adenosine Deaminase Deficiency
Adenylosuccinate Lyase Deficiency
AICA-Ribosiduria
Molybdenum Cofactor Deficiency
Purine Nucleoside Phosphorylase Deficiency
Xanthine Dehydrogenase Deficiency (Xanthinuria)
4-Hydroxybutyric Aciduria/Succinic Semialdehyde Dehydrogenase Deficiency
Azithromycin Action Pathway
Clarithromycin Action Pathway
Clindamycin Action Pathway
Erythromycin Action Pathway
Roxithromycin Action Pathway
Telithromycin Action Pathway
Amikacin Action Pathway
Gentamicin Action Pathway
Kanamycin Action Pathway
Neomycin Action Pathway
Netilmicin Action Pathway
Spectinomycin Action Pathway
Streptomycin Action Pathway
Clomocycline Action Pathway
Demeclocycline Action Pathway
Doxycycline Action Pathway
Minocycline Action Pathway
Oxytetracycline Action Pathway
Tetracycline Action Pathway
Lymecycline Action Pathway
Hyperinsulinism-Hyperammonemia Syndrome
Lesch-Nyhan Syndrome (LNS)
Gout or Kelley-Seegmiller Syndrome
Homocarnosinosis
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
Succinic semialdehyde dehydrogenase deficiency
Tobramycin Action Pathway
Tigecycline Action Pathway
Arbekacin Action Pathway
Paromomycin Action Pathway
Rolitetracycline Action Pathway
Methacycline Action Pathway
Lincomycin Action Pathway
Chloramphenicol Action Pathway
Troleandomycin Action Pathway
Josamycin Action Pathway
StateSolid
Water Solubility3.56e+00 g/l
logP-1.99
logS-2.01
pKa (Strongest Acidic)1.05
pKa (Strongest Basic)1.73
Hydrogen Acceptor Count10
Hydrogen Donor Count6
Polar Surface Area201.75 Ų
Rotatable Bond Count4
Physiological Charge-2
Formal Charge0
Refractivity75.49 m³·mol⁻¹
Polarizability30.70

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