Record Information
Version1.0
Creation date2011-09-21 01:38:21 UTC
Update date2015-07-21 06:59:23 UTC
Primary IDFDB028348
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name2,6-Diamino-4-hydroxy-5-N-methylformamidopyrimidine
Description2,6-Diamino-4-hydroxy-5-N-methylformamidopyrimidine is a methylated derivative of 2,6-Diamino-4-hydroxy-5-N-formamidopyrimidine or FapyGua. It is produced by DNA-formamidopyrimidine glycosylase (EC 3.2.2.23). This enzyme catalyzes the hydrolysis of DNA containing ring-opened 7-methylguanine residues, releasing 2,6-diamino-4-hydroxy-5-(N-methyl)formamidopyrimidine. More specifically, this enzyme catalyzes the removal of oxidized purine bases by cleaving the N-C1' glycosidic bond between the oxidized purine and the deoxyribose sugar. The reaction involves the formation of a covalent enzyme substrate intermediate. Release of the enzyme and free base by a beta-elimination or a beta, gamma-elimination mechanism results in the cleavage of the DNA backbone 3' of the apurinic (AP) site. The presence of this compound in urine is indicative of oxidative damage to DNA (oxidized purine base lesions) [HMDB]
CAS Number77440-13-2
Structure
Thumb
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility16.3 g/LALOGPS
logP-0.76ALOGPS
logP-0.99ChemAxon
logS-1ALOGPS
pKa (Strongest Acidic)11.96ChemAxon
pKa (Strongest Basic)2.86ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area118.36 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity48.17 m³·mol⁻¹ChemAxon
Polarizability16.81 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC6H9N5O2
IUPAC nameN-(2,4-diamino-6-hydroxypyrimidin-5-yl)-N-methylformamide
InChI IdentifierInChI=1S/C6H9N5O2/c1-11(2-12)3-4(7)9-6(8)10-5(3)13/h2H,1H3,(H5,7,8,9,10,13)
InChI KeyCGWDNAFNQOBSCK-UHFFFAOYSA-N
Isomeric SMILESCN(C=O)C1=C(N)N=C(N)N=C1O
Average Molecular Weight183.168
Monoisotopic Molecular Weight183.075624557
Classification
Description Belongs to the class of organic compounds known as hydroxypyrimidines. These are organic compounds containing a hydroxyl group attached to a pyrimidine ring. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazines
Sub ClassPyrimidines and pyrimidine derivatives
Direct ParentHydroxypyrimidines
Alternative Parents
Substituents
  • Aminopyrimidine
  • Hydroxypyrimidine
  • Hydropyrimidine
  • Tertiary carboxylic acid amide
  • Heteroaromatic compound
  • Amino acid or derivatives
  • Carboxamide group
  • Azacycle
  • Carboxylic acid derivative
  • Organopnictogen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Amine
  • Carbonyl group
  • Organic nitrogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS2,6-Diamino-4-hydroxy-5-N-methylformamidopyrimidine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0kai-2900000000-a67d7f80d254667fa8aeSpectrum
Predicted GC-MS2,6-Diamino-4-hydroxy-5-N-methylformamidopyrimidine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0itd-1390000000-7af95ca919277dda70d8Spectrum
Predicted GC-MS2,6-Diamino-4-hydroxy-5-N-methylformamidopyrimidine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2,6-Diamino-4-hydroxy-5-N-methylformamidopyrimidine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-053r-0900000000-161782a982bd9e0f746b2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a59-0900000000-8aabbbca1867aa5ee4702017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-9200000000-79543490b30fc623afa92017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-1a59e57626ce37c5638e2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0w29-2900000000-e8832d2c064b269233012017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9300000000-78862d713f4e4a8092902017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-053r-0900000000-7cddc5f02d68b5f58fe52021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0540-0900000000-1299b98119aa35f053c72021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-007d-9200000000-3b5b503fd38c061918692021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-c5ca8ed84c0281e2cfb32021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gw0-3900000000-4ce1f6206fd7400e51ec2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9200000000-afeccf534860ddaa88be2021-09-23View Spectrum
NMRNot Available
ChemSpider ID113157
ChEMBL IDNot Available
KEGG Compound IDC04744
Pubchem Compound ID127546
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB11657
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference