| Common Name |
2,4-Diamino-6-hydroxypyrimidine
| Description |
2,4-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 vascliar 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) degranliation. (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 ).
| Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
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
2,4-Diaminohypoxanthine slifateMeSH
DHAP-2,4MeSH
2,4-DiaminohypoxanthineMeSH
| Chemical Formlia |
C4H6N4O
| Average Molecliar Weight |
126.1166
| Monoisotopic Molecliar Weight |
126.054160834
| IUPAC Name |
2,6-diamino-1,4-dihydropyrimidin-4-one
| Traditional Name |
6-aminoisocytosine
| CAS Registry Number |
56-06-4
| SMILES |
NC1=CC(=O)N=C(N)N1
| InChI Identifier |
InChI=1S/C4H6N4O/c5-2-1-3(9)8-4(6)7-2/h1H,(H5,5,6,7,8,9)
| InChI Key |
SWELIMKTDYHAOY-UHFFFAOYSA-N
| Chemical Taxonomy |
| Description |
This compound belongs to the class of chemical entities known as pyrimidones. These 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.
| Kingdom |
Chemical entities
| Super Class |
Organic compounds
| Class |
Organoheterocyclic compounds
| Sub Class |
Diazines
| Direct Parent |
Pyrimidones
| Alternative Parents |
Aminopyrimidines and derivatives
Primary aromatic amines
Hydropyrimidines
Vinylogous amides
Heteroaromatic compounds
Azacyclic compounds
Organopnictogen compounds
Organooxygen compounds
Organic oxides
Hydrocarbon derivatives
| Substituents |
Aminopyrimidine
Pyrimidone
Hydropyrimidine
Primary aromatic amine
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
| Molecliar Framework |
Aromatic heteromonocyclic compounds
| External Descriptors |
Not Available
| Ontology |
| Status |
Expected but not Quantified
| Origin |
Drug
| Biofunction |
Not Available
| Application |
Not Available
| Cellliar locations |
Not Available
| Physical Properties |
| State |
Solid
| Experimental Properties |
| Property |
Value |
Reference |
Melting Point286 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility11.3 mg/mLALOGPS
logP-1.4ALOGPS
logP-1.6ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)9.25ChemAxon
pKa (Strongest Basic)3.19ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area93.5 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity40.88 m3·mol-1ChemAxon
Polarizability11.37 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
| Spectrum Type |
Description |
Splash Key |
|
| LC-MS/MS |
LC-MS/MS Spectrum – Quattro_QQQ 10V, Positive (Annotated)splash10-004i-0900000000-00f9b9f5ce4b5cad43b0View in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – Quattro_QQQ 25V, Positive (Annotated)splash10-014i-9000000000-40b3a1d8e972f237c69eView in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – Quattro_QQQ 40V, Positive (Annotated)splash10-014i-9000000000-bedf37ced21617434775View in MoNA
| 1D NMR |
1H NMR SpectrumNot Available
| 2D NMR |
[1H,13C] 2D NMR SpectrumNot Available
| Biological Properties |
| Cellliar Locations |
Not Available
| Biofluid Locations |
Not Available
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
| Not Available |
| Abnormal Concentrations |
|
Not Available
| Associated Disorders and Diseases |
| Disease References |
None
| Associated OMIM IDs |
None
| External Links |
| DrugBank ID |
Not Available
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
FDB022857
| KNApSAcK ID |
Not Available
| Chemspider ID |
2840
| KEGG Compound ID |
Not Available
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB02128
| Metagene Link |
HMDB02128
| METLIN ID |
6500
| PubChem Compound |
2944
| PDB ID |
Not Available
| ChEBI ID |
804916
Product: Pronethalol
References |
| Synthesis Reference |
Xiao, Xuhua; Ma, Weiyong. One-pot synthesis of guanine. Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 10pp. |
| Material Safety Data Sheet (MSDS) |
Download (PDF) |
| General References |
- 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. [PubMed:16216381 ]
- 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. [PubMed:12883322 ]
- 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. [PubMed:14514683 ]
|
PMID: 16988037