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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-10-30 10:32:48 UTC
Update Date2019-07-23 07:12:35 UTC
HMDB IDHMDB0059612
Secondary Accession Numbers
  • HMDB59612
Metabolite Identification
Common Name7-Methylguanosine 5'-phosphate
Description7-Methylguanosine 5'-phosphate, also known as N7-methyl-GMP, belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). 7-Methylguanosine 5'-phosphate is a moderately basic compound (based on its pKa).
Structure
Data?1563865955
Synonyms
ValueSource
7-Methylguanosine 5'-(dihydrogen phosphate)ChEBI
N7-Methyl-GMPKegg
7-Methylguanosine 5'-(dihydrogen phosphoric acid)Generator
7-Methylguanosine 5'-phosphoric acidGenerator
7-Methylguanosine 5'-phosphoric acid(1+)HMDB
7-Methyl GMPHMDB
7-Methylguanosine-5'-monophosphateHMDB
7-Methylguanosine 5'-phosphateChEBI
Chemical FormulaC11H17N5O8P
Average Molecular Weight378.2551
Monoisotopic Molecular Weight378.081474057
IUPAC Name9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]-6-hydroxy-2-imino-7-methyl-3,9-dihydro-2H-purin-7-ium
Traditional Name7-methyl-5'-guanylic acid
CAS Registry NumberNot Available
SMILES
C[N+]1=CN([C@@H]2O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]2O)C2=C1C(O)=NC(=N)N2
InChI Identifier
InChI=1S/C11H16N5O8P/c1-15-3-16(8-5(15)9(19)14-11(12)13-8)10-7(18)6(17)4(24-10)2-23-25(20,21)22/h3-4,6-7,10,17-18H,2H2,1H3,(H4-,12,13,14,19,20,21,22)/p+1/t4-,6-,7-,10-/m1/s1
InChI KeyAOKQNZVJJXPUQA-KQYNXXCUSA-O
Chemical Taxonomy
Description belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids
Alternative Parents
Substituents
  • Alpha-amino acid
  • Thiomorpholine-3-carboxylic acid
  • 1,4-thiazinane
  • Amino acid
  • Carboxylic acid
  • Secondary aliphatic amine
  • Monocarboxylic acid or derivatives
  • Secondary amine
  • Thioether
  • Dialkylthioether
  • Organoheterocyclic compound
  • Azacycle
  • Carbonyl group
  • Organooxygen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic nitrogen compound
  • Amine
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.29 g/LALOGPS
logP-2.7ALOGPS
logP-7.4ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)1.19ChemAxon
pKa (Strongest Basic)2.34ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area193.73 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity91.27 m³·mol⁻¹ChemAxon
Polarizability33.07 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052b-8924000000-f8f42bc2d9a0a1ffcfe0Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-004s-9552170000-ea1b809ecc5737896218Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-1009000000-ac11a6e5e6554d3a3c24Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0092-6319000000-7cbaca15e0785ea54c87Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0007-9620000000-fc0c9105ecabc0c0638fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-2009000000-79b6a021245376c6f57bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9001000000-cb44126030b7725e7b55Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-87084a5c45da50c8a346Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB03593
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC03998
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440190
PDB IDG7M
ChEBI ID17825
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Not Available
Specific function:
Decapping scavenger enzyme that catalyzes the cleavage of a residual cap structure following the degradation of mRNAs by the 3'->5' exosome-mediated mRNA decay pathway. Hydrolyzes cap analog structures like 7-methylguanosine nucleoside triphosphate (m7GpppG) with up to 10 nucleotide substrates (small capped oligoribonucleotides) and specifically releases 5'-phosphorylated RNA fragments and 7-methylguanosine monophosphate (m7GMP). Cleaves cap analog structures like tri-methyl guanosine nucleoside triphosphate (m3(2,2,7)GpppG) with very poor efficiency. Does not hydrolyze unmethylated cap analog (GpppG) and shows no decapping activity on intact m7GpppG-capped mRNA molecules longer than 25 nucleotides. Does not hydrolyze 7-methylguanosine diphosphate (m7GDP) to m7GMP (PubMed:22985415). May also play a role in the 5'->3 mRNA decay pathway; m7GDP, the downstream product released by the 5'->3' mRNA mediated decapping activity, may be also converted by DCPS to m7GMP (PubMed:14523240). Binds to m7GpppG and strongly to m7GDP. Plays a role in first intron splicing of pre-mRNAs. Inhibits activation-induced cell death.
Gene Name:
DCPS
Uniprot ID:
Q96C86
Molecular weight:
38608.45
Reactions
M(7)G5'ppp5'N(3'ppp5'N)(n) + Water → 7-Methylguanosine 5'-phosphate + pp5'N(3'ppp5'N)(n)details
7-Methylguanosine 5'-diphosphate + Water → 7-Methylguanosine 5'-phosphate + Phosphatedetails