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2-amino-6-(hydroxymethyl)-7,8-dihydropteridin-4-ol (YMDB00149)

Identification
YMDB IDYMDB00149
Name2-amino-6-(hydroxymethyl)-7,8-dihydropteridin-4-ol
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionDihydropterin-CH2OH (6-hydroxymethyl-7,8-dihydropterin) is the precursor to dihydropterin-CH2OH-PP (6-hydroxymethyl-7,8-dihydropterin diphosphate) in the 6-hydroxymethyl-dihydropterin diphosphate biosynthesis pathway. 6-Hydroxymethyl-dihydropterin diphosphate is the pterin precursor for the biosynthesis of several important cofactors, including tetrahydrofolate, methanopterin and sarcinapterin. [Biocyc PWY-6147]
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 2-Amino-4-hydroxy-6-hydroxymethyl-7,8-dihydropteridine
  • HMDP CPD
CAS number3672-03-5
WeightAverage: 195.1787
Monoisotopic: 195.075624557
InChI KeyCQQNNQTXUGLUEV-UHFFFAOYSA-N
InChIInChI=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)
IUPAC Name2-amino-6-(hydroxymethyl)-3,4,7,8-tetrahydropteridin-4-one
Traditional IUPAC Name2-amino-6-(hydroxymethyl)-7,8-dihydro-3H-pteridin-4-one
Chemical FormulaC7H9N5O2
SMILESNC1=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
StateNot Available
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
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
  • mitochondrion
Organoleptic PropertiesNot Available
SMPDB Pathways
tetrahydrofolate biosynthesisPW002417 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Folate biosynthesisec00790 Map00790
SMPDB Reactions
7,8-Dihydroneopterin → Glycolaldehyde + 2-amino-6-(hydroxymethyl)-7,8-dihydropteridin-4-ol
2-amino-6-(hydroxymethyl)-7,8-dihydropteridin-4-ol + Adenosine triphosphate → Adenosine monophosphate + hydron + (2-amino-4-hydroxy-7,8-dihydropteridin-6-yl)methyl diphosphate
KEGG Reactions
2-amino-6-(hydroxymethyl)-7,8-dihydropteridin-4-ol + Adenosine triphosphate → Adenosine monophosphate + (2-Amino-4-hydroxy-7,8-dihydropteridin-6-yl)methyl trihydrogen diphosphate + hydron
7,8-Dihydroneopterin → Glycolaldehyde + 2-amino-6-(hydroxymethyl)-7,8-dihydropteridin-4-ol
2-amino-6-(hydroxymethyl)-7,8-dihydropteridin-4-ol + 4-Aminobenzoic acid → water + 7,8-Dihydropteroic acid
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-02t9-1900000000-5cfea5c037994f006216JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0900000000-9f8713d042cc448282c0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0900000000-443afedc044efb6836efJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01p9-2900000000-143274abf0f8afadfb00JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-7d20bbe8055a463789f9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01r6-1900000000-56b39cb20c728828c72aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9200000000-32e7a15f26d685ec66bcJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-e6264bd1af5f7597a2c4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0900000000-2046c8dbdea1405f54d1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004l-4900000000-8df0786ac08c282820b0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-d9a36ecaf7ce4795a113JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-1900000000-695ce544726c989be876JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9400000000-441d6e22f231bf631645JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Fernley, R. T., Iliades, P., Macreadie, I. (2007). "A rapid assay for dihydropteroate synthase activity suitable for identification of inhibitors." Anal Biochem 360:227-234.17134675
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID17083
HMDB IDHMDB0304227
Pubchem Compound ID218
Kegg IDC01300
ChemSpider ID213
FOODB IDFDB030597
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. Folic acid synthesis protein FOL1
General function:
Involved in dihydropteroate synthase activity
Specific function:
Catalyzes three sequential steps of tetrahydrofolate biosynthesis
Gene Name:
FOL1
Uniprot ID:
P53848
Molecular weight:
93119.10156
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.
ATP + 2-amino-4-hydroxy-6-hydroxymethyl-7,8-dihydropteridine → AMP + (2-amino-4-hydroxy-7,8-dihydropteridin-6-yl)methyl diphosphate.
(2-amino-4-hydroxy-7,8-dihydropteridin-6-yl)methyl diphosphate + 4-aminobenzoate → diphosphate + dihydropteroate.