Record Information
Version1.0
Creation date2011-09-21 00:20:39 UTC
Update date2015-10-09 22:31:47 UTC
Primary IDFDB022857
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name2,4-Diamino-6-hydroxypyrimidine
Description2,4-Diamino-6-hydroxypyrimidine (DAHP) is a selective inhibitor of GTP cyclohydrolase I (GTPCH) that restricts the de novo synthesis of tetrahydrobiopterin (BH4) or the BH4 precursor in vascular smooth muscle cells (VSMC). (PMID 12883322) 2,4-Diamino-6-hydroxypyrimidine also inhibits nitric oxide (NO) in both Interferon-gamma (IFN-gamma) and antigen (Ag)/IgE (Ag/IgE) systems, increasing Mast cells (MC) degranulation. (PMID 14514683) Sepiapterin, a precursor to tetrahydrobiopterin in the salvage pathway, completely reverses the effect of 2,4-diamino-6-hydroxypyrimidine on neuronal NO-synthase (nNOS) ubiquitylation. (PMID 16216381) [HMDB]
CAS Number56-06-4
Structure
Thumb
Synonyms
SynonymSource
2,4-diamino-6-PyrimidinoneHMDB
2,6-diamino-4(1H)-PyrimidinoneHMDB
2,6-diamino-4(3H)-PyrimidinoneHMDB
2,6-diamino-4-HydroxypyrimidineHMDB
2,6-diamino-4-PyrimidinolHMDB
2,6-Diaminopyrimidin-4-oneHMDB
6-AminoisocytosineHMDB
6-Hydroxy-2,4-pyrimidinediamineHMDB
2,4-DAHPMeSH, HMDB
2,4-Diaminohypoxanthine sulfateMeSH, HMDB
DHAP-2,4MeSH, HMDB
2,4-DiaminohypoxanthineMeSH, HMDB
2,4-Diamino-6-hydroxypyrimidineMeSH
2,4-Diamino-6-pyrimidinonehmdb
2,6-Diamino-4-hydroxypyrimidinehmdb
2,6-Diamino-4-pyrimidinolhmdb
2,6-Diamino-4(1H)-pyrimidinonehmdb
2,6-Diamino-4(3H)-pyrimidinonehmdb
Predicted Properties
PropertyValueSource
Water Solubility11.3 g/LALOGPS
logP-1.4ALOGPS
logP-1.6ChemAxon
logS-1ALOGPS
pKa (Strongest Acidic)15.84ChemAxon
pKa (Strongest Basic)1.36ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area93.5 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity40.88 m³·mol⁻¹ChemAxon
Polarizability11.37 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC4H6N4O
IUPAC name2,6-diamino-1,4-dihydropyrimidin-4-one
InChI IdentifierInChI=1S/C4H6N4O/c5-2-1-3(9)8-4(6)7-2/h1H,(H5,5,6,7,8,9)
InChI KeySWELIMKTDYHAOY-UHFFFAOYSA-N
Isomeric SMILESNC1=CC(=O)N=C(N)N1
Average Molecular Weight126.1166
Monoisotopic Molecular Weight126.054160834
Classification
Description Belongs to the class of organic compounds known as pyrimidones. Pyrimidones are compounds that contain a pyrimidine ring, which bears a ketone. 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 ParentPyrimidones
Alternative Parents
Substituents
  • Aminopyrimidine
  • Pyrimidone
  • Hydropyrimidine
  • Vinylogous amide
  • Heteroaromatic compound
  • Azacycle
  • Amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Role

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS2,4-Diamino-6-hydroxypyrimidine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004i-4900000000-1e063b05226e8896a663Spectrum
Predicted GC-MS2,4-Diamino-6-hydroxypyrimidine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-004i-0900000000-00f9b9f5ce4b5cad43b02012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-014i-9000000000-40b3a1d8e972f237c69e2012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014i-9000000000-bedf37ced216174347752012-07-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-5e3c38e0a0a648095bbd2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-2900000000-b08fbf010a25872f527e2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000f-9000000000-37474e4ea02c53c6dbbf2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-2900000000-33f401e4d08da16fa38f2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-3900000000-d44c471a63adfa0360322017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000x-9000000000-515cef0906e879cd3b672017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-17e49b273de10b22c70b2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002f-9200000000-f64008e5d2bac657c5a42021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-9000000000-8fe725f865981c7d648f2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-7900000000-8ac5ea6d8dbacebc0edf2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-76ada99b8a779fab63d82021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9000000000-9c42190a2a1ee0031cf72021-09-24View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 400 MHz, H2O, experimental)Spectrum
ChemSpider ID2840
ChEMBL IDCHEMBL1255934
KEGG Compound IDNot Available
Pubchem Compound ID2944
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB02128
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
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference