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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
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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)10.91ChemAxon
pKa (Strongest Basic)3.9ChemAxon
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-DihydroneopterinGlycolaldehyde + 2-amino-6-(hydroxymethyl)-7,8-dihydropteridin-4-ol
2-amino-6-(hydroxymethyl)-7,8-dihydropteridin-4-ol + Adenosine triphosphateAdenosine 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 triphosphateAdenosine monophosphate + (2-Amino-4-hydroxy-7,8-dihydropteridin-6-yl)methyl trihydrogen diphosphate + hydron
7,8-DihydroneopterinGlycolaldehyde + 2-amino-6-(hydroxymethyl)-7,8-dihydropteridin-4-ol
2-amino-6-(hydroxymethyl)-7,8-dihydropteridin-4-ol + 4-Aminobenzoic acidwater + 7,8-Dihydropteroic acid
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
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 IDNot Available
Pubchem Compound ID218
Kegg IDC01300
ChemSpider ID213
FOODB IDFDB030597
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

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.