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2,4-Diamino-6-hydroxypyrimidine (PC000653)

Record Information
Version1.0
Creation date2015-10-09 22:31:47 UTC
Update date2017-01-19 02:36:31 UTC
FoodComEx IDPC000653
FoodDB RecordFDB022857
Chemical Information
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
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
2,4-Diamino-6-hydroxypyrimidinehmdb
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
2,6-Diaminopyrimidin-4-onehmdb
6-Aminoisocytosinehmdb
6-Hydroxy-2,4-pyrimidinediaminehmdb
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
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
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logPNot Available
Experimental Water SolubilityNot Available
Melting PointNot Available
Foods of Origin
FoodContent Range AverageReference
FoodReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 1 g
Delivery TimeNot Available
Storage Formsolid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectra
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez Fresnovazquezf@ualberta.ca
Commercial Vendors
AKSci D423
AKSci J92611
Cayman Chemical 81260
Toronto Research Chemicals D416353