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2-Amino-4-hydroxy-6-hydroxymethyl-7,8-dihydropteridine (M2MDB001880)

Record Information
Version2.0
Creation Date2012-08-09 09:25:06 -0600
Update Date2015-06-03 17:21:37 -0600
Secondary Accession Numbers
  • ECMDB21485
Identification
Name:2-Amino-4-hydroxy-6-hydroxymethyl-7,8-dihydropteridine
Description2-amino-4-hydroxy-6-hydroxymethyl-7,8-dihydropteridine is a member of the chemical class known as Pterins and Derivatives. These are polycyclic aromatic compounds containing a pterin moeity, which consist of a pteridine ring bearing a ketone and an amine group to form 2-aminopteridin-4(3H)-one. 2-amino-4-hydroxy-6-hydroxymethyl-7,8-dihydropteridine is invovled in Folate biosynthesis. (KEGG)
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • 2-Amino-4-hydroxy-6-hydroxymethyl-7,8-dihydropteridine
  • 2-Amino-6-(hydroxymethyl)-7,8-dihydropteridin-4-ol
  • HMeDHP
Chemical Formula:C7H9N5O2
Weight:Average: 195.1787
Monoisotopic: 195.075624557
InChI Key:CQQNNQTXUGLUEV-UHFFFAOYSA-N
InChI:InChI=1S/C7H9N5O2/c8-7-11-5-4(6(14)12-7)10-3(2-13)1-9-5/h13H,1-2H2,(H4,8,9,11,12,14)
CAS number:3672-03-5
IUPAC Name:2-amino-6-(hydroxymethyl)-3,4,7,8-tetrahydropteridin-4-one
Traditional IUPAC Name:2-amino-6-(hydroxymethyl)-7,8-dihydro-3H-pteridin-4-one
SMILES:NC1=NC2=C(N=C(CO)CN2)C(=O)N1
Chemical Taxonomy
Description belongs to the class of organic compounds known as pterins and derivatives. These are polycyclic aromatic compounds containing a pterin moiety, which consist of a pteridine ring bearing a ketone and an amine group to form 2-aminopteridin-4(3H)-one.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPteridines and derivatives
Sub ClassPterins and derivatives
Direct ParentPterins and derivatives
Alternative Parents
Substituents
  • Pterin
  • Secondary aliphatic/aromatic amine
  • Hydroxypyrimidine
  • Pyrimidine
  • Heteroaromatic compound
  • Ketimine
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Secondary amine
  • Alcohol
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Imine
  • Amine
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:0
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility2.47 g/LALOGPS
logP-1.7ALOGPS
logP-1.9ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)7.62ChemAxon
pKa (Strongest Basic)0.76ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area112.1 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity57.86 m³·mol⁻¹ChemAxon
Polarizability18.4 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-02t9-1900000000-5cfea5c037994f006216View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0900000000-9f8713d042cc448282c0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0900000000-443afedc044efb6836efView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01p9-2900000000-143274abf0f8afadfb00View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-7d20bbe8055a463789f9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01r6-1900000000-56b39cb20c728828c72aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9200000000-32e7a15f26d685ec66bcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-e6264bd1af5f7597a2c4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0900000000-2046c8dbdea1405f54d1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004l-4900000000-8df0786ac08c282820b0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-d9a36ecaf7ce4795a113View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-1900000000-695ce544726c989be876View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9400000000-441d6e22f231bf631645View in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID17083
HMDB IDHMDB0304227
Pubchem Compound ID218
Kegg IDC01300
ChemSpider ID213
Wikipedia IDNot Available
BioCyc IDNot Available
Ligand ExpoPH2

Enzymes

Protein Details
1. Dihydroneopterin aldolase
General function:
Involved in dihydroneopterin aldolase activity
Specific function:
Catalyzes the conversion of 7,8-dihydroneopterin to 6- hydroxymethyl-7,8-dihydropterin. Can use L-threo-dihydroneopterin and D-erythro-dihydroneopterin as substrates for the formation of 6-hydroxymethyldihydropterin, but it can also catalyze the epimerization of carbon 2' of dihydroneopterin and dihydromonapterin at appreciable velocity
Gene Name:
folB
Uniprot ID:
P0AC16
Molecular weight:
13619
Reactions
2-amino-4-hydroxy-6-(D-erythro-1,2,3-trihydroxypropyl)-7,8-dihydropteridine = 2-amino-4-hydroxy-6-hydroxymethyl-7,8-dihydropteridine + glycolaldehyde.