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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2009-02-04 14:42:31 UTC
Update Date2017-12-07 02:32:11 UTC
HMDB IDHMDB0011690
Secondary Accession Numbers
  • HMDB11690
Metabolite Identification
Common Name7-Aminomethyl-7-carbaguanine
Description7-Aminomethyl-7-carbaguanine is one of the precursors of nucleoside Q (queuosine) biosynthesis. It is a substrate for preQ1 synthase (EC 1.7.1.13) which catalyzes the NADPH-dependent reduction of 7-cyano-7-carbaguanine (preQ0) to 7-aminomethyl-7-carbaguanine (preQ1). More specifically, this enzyme catalyzes the chemical reaction. 7-aminomethyl-7-carbaguanine + 2 NADP+ <-> 7-cyano-7-carbaguanine + 2 NADPH + 2 H+.
Structure
Thumb
Synonyms
ValueSource
7-DEAZA-7-aminomethyl-guanineChEBI
7-Aminomethyl-7-deazaguanineHMDB
PreQ1HMDB
Chemical FormulaC7H9N5O
Average Molecular Weight179.1793
Monoisotopic Molecular Weight179.080709935
IUPAC Name2-amino-5-(aminomethyl)-3H,4H,7H-pyrrolo[2,3-d]pyrimidin-4-one
Traditional Name7-aminomethyl-7-deazaguanine
CAS Registry NumberNot Available
SMILES
NCC1=CNC2=C1C(=O)NC(N)=N2
InChI Identifier
InChI=1S/C7H9N5O/c8-1-3-2-10-5-4(3)6(13)12-7(9)11-5/h2H,1,8H2,(H4,9,10,11,12,13)
InChI KeyMEYMBLGOKYDGLZ-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as pyrrolo[2,3-d]pyrimidines. These are aromatic heteropolycyclic compounds containing a pyrrolo[2,3-d]pyrimidine ring system, which is an pyrrolopyrimidine isomers having the 3 ring nitrogen atoms at the 1-, 5-, and 7-positions.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyrrolopyrimidines
Sub ClassPyrrolo[2,3-d]pyrimidines
Direct ParentPyrrolo[2,3-d]pyrimidines
Alternative Parents
Substituents
  • Pyrrolo[2,3-d]pyrimidine
  • Aralkylamine
  • Hydroxypyrimidine
  • Substituted pyrrole
  • Pyrimidine
  • Heteroaromatic compound
  • Pyrrole
  • Azacycle
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Amine
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source:

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 Solubility2.93 g/LALOGPS
logP-1.4ALOGPS
logP-1.2ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)11.04ChemAxon
pKa (Strongest Basic)8.6ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area109.29 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity48.67 m³·mol⁻¹ChemAxon
Polarizability17.44 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-06vr-1900000000-6c74d2d331883324fbd8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03e9-0900000000-186cf56f77e8ac46162eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0900000000-e42a8c4daace1afde7aeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0229-1900000000-d9d17cbc8d643eb3bb92View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-7c00db685d48eeeaa166View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004j-2900000000-8a8ba88dc9cf497add5eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9600000000-8d2f3dc2af852732e95bView in MoNA
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 IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB028377
KNApSAcK IDNot Available
Chemspider ID166
KEGG Compound IDC16675
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound171
PDB IDPRF
ChEBI ID45126
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in queuine tRNA-ribosyltransferase activity
Specific function:
Interacts with QTRTD1 to form an active queuine tRNA-ribosyltransferase. This enzyme exchanges queuine for the guanine at the wobble position of tRNAs with GU(N) anticodons (tRNA-Asp, -Asn, -His and -Tyr), thereby forming the hypermodified nucleoside queuosine (Q) (7-(((4,5-cis-dihydroxy-2-cyclopenten-1-yl)amino)methyl)-7-deazaguanosine) (By similarity).
Gene Name:
QTRT1
Uniprot ID:
Q9BXR0
Molecular weight:
44047.3
Reactions
tRNA guanine + 7-Aminomethyl-7-carbaguanine → tRNA 7-aminomethyl-7-carbaguanine + Guaninedetails
General function:
Involved in queuine tRNA-ribosyltransferase activity
Specific function:
Interacts with QTRT1 to form an active queuine tRNA-ribosyltransferase. This enzyme exchanges queuine for the guanine at the wobble position of tRNAs with GU(N) anticodons (tRNA-Asp, -Asn, -His and -Tyr), thereby forming the hypermodified nucleoside queuosine (Q) (7-(((4,5-cis-dihydroxy-2-cyclopenten-1-yl)amino)methyl)-7-deazaguanosine) (By similarity).
Gene Name:
QTRTD1
Uniprot ID:
Q9H974
Molecular weight:
48203.07
Reactions
tRNA guanine + 7-Aminomethyl-7-carbaguanine → tRNA 7-aminomethyl-7-carbaguanine + Guaninedetails