2,4-Diamino-6-hydroxypyrimidine (CHEM020248)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 06:57:14 UTC
Update Date2026-04-17 17:45:33 UTC
Accession NumberCHEM020248
Identification
Common Name2,4-Diamino-6-hydroxypyrimidine
ClassSmall Molecule
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).
Contaminant Sources
  • FooDB Chemicals
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
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
Chemical FormulaC4H6N4O
Average Molecular Mass126.117 g/mol
Monoisotopic Mass126.054 g/mol
CAS Registry Number56-06-4
IUPAC Name2,6-diamino-1,4-dihydropyrimidin-4-one
Traditional Name6-aminoisocytosine
SMILESNC1=CC(=O)N=C(N)N1
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
Chemical Taxonomy
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-4900000000-1e063b05226e8896a663Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-004i-0900000000-00f9b9f5ce4b5cad43b0Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-014i-9000000000-40b3a1d8e972f237c69eSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014i-9000000000-bedf37ced21617434775Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-5e3c38e0a0a648095bbdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-2900000000-b08fbf010a25872f527eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000f-9000000000-37474e4ea02c53c6dbbfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-2900000000-33f401e4d08da16fa38fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-3900000000-d44c471a63adfa036032Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000x-9000000000-515cef0906e879cd3b67Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-17e49b273de10b22c70bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002f-9200000000-f64008e5d2bac657c5a4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-9000000000-8fe725f865981c7d648fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-7900000000-8ac5ea6d8dbacebc0edfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-76ada99b8a779fab63d8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9000000000-9c42190a2a1ee0031cf7Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0002128
FooDB IDFDB022857
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID6500
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID2840
ChEBI ID804916
PubChem Compound ID2944
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Xiao, Xuhua; Ma, Weiyong. One-pot synthesis of guanine. Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 10pp.
2. Yoshida M, Nakanishi N, Wang X, Hattori Y: Exogenous biopterins requirement for iNOS function in vascular smooth muscle cells. J Cardiovasc Pharmacol. 2003 Aug;42(2):197-203.
3. Gilchrist M, Hesslinger C, Befus AD: Tetrahydrobiopterin, a critical factor in the production and role of nitric oxide in mast cells. J Biol Chem. 2003 Dec 12;278(50):50607-14. Epub 2003 Sep 26.
4. Kamada Y, Jenkins GJ, Lau M, Dunbar AY, Lowe ER, Osawa Y: Tetrahydrobiopterin depletion and ubiquitylation of neuronal nitric oxide synthase. Brain Res Mol Brain Res. 2005 Dec 7;142(1):19-27. Epub 2005 Oct 10.