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(2-Amino-4-hydroxy-7,8-dihydropteridin-6-yl)methyl trihydrogen diphosphate (YMDB00430)

Identification
YMDB IDYMDB00430
Name(2-Amino-4-hydroxy-7,8-dihydropteridin-6-yl)methyl trihydrogen diphosphate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description(2-amino-4-hydroxy-7,8-dihydropteridin-6-yl)methyl diphosphate(3-), also known as 2-amino-4-hydroxy-6-hydroxymethyl-7,8-dihydropteridine diphosphoric acid or 2-amino-7,8-dihydro-4-hydroxy-6-(diphosphooxymethyl)pteridine, 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 (2-amino-4-hydroxy-7,8-dihydropteridin-6-yl)methyl diphosphate(3-) is an extremely strong basic compound (based on its pKa) (2-amino-4-hydroxy-7,8-dihydropteridin-6-yl)methyl diphosphate(3-) exists in both E. coli (prokaryote) and yeast (eukaryote).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 2-Amino-4-hydroxy-6-hydroxymethyl-7,8-dihydropteridine diphosphate
  • 2-amino-4-hydroxy-6-pyrophosphoryl-methylpteridine
  • 2-Amino-7,8-dihydro-4-hydroxy-6-(diphosphooxymethyl)pteridine
  • 7,8-Dihydropterin pyrophosphate
  • Pteridine diphosphate
  • (7,8-Dihydropterin-6-yl)methyl diphosphate
  • 2-Amino-4-hydroxy-6-hydroxymethyl-7,8-dihydropteridine diphosphoric acid
  • 7,8-Dihydropterin pyrophosphoric acid
  • Pteridine diphosphoric acid
  • (7,8-Dihydropterin-6-yl)methyl diphosphoric acid
  • (2-Amino-4-hydroxy-7,8-dihydropteridin-6-yl)methyl diphosphoric acid(3-)
  • (2-amino-4-Hydroxy-7,8-dihydropteridin-6-yl)methyl trihydrogen diphosphoric acid
  • 6-Hydroxymethyl-7,8-dihydropterin diphosphoric acid
CAS number3545-84-4
WeightAverage: 355.1385
Monoisotopic: 355.008285377
InChI KeyFCQGJGLSOWZZON-UHFFFAOYSA-N
InChIInChI=1S/C7H11N5O8P2/c8-7-11-5-4(6(13)12-7)10-3(1-9-5)2-19-22(17,18)20-21(14,15)16/h1-2H2,(H,17,18)(H2,14,15,16)(H4,8,9,11,12,13)
IUPAC Name({[(2-amino-4-oxo-3,4,7,8-tetrahydropteridin-6-yl)methoxy](hydroxy)phosphoryl}oxy)phosphonic acid
Traditional IUPAC Name[(2-amino-4-oxo-7,8-dihydro-3H-pteridin-6-yl)methoxy(hydroxy)phosphoryl]oxyphosphonic acid
Chemical FormulaC7H11N5O8P2
SMILESNC1=NC2=C(N=C(COP(O)(=O)OP(O)(O)=O)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
  • Organic pyrophosphate
  • Aminopyrimidine
  • Pyrimidone
  • Monoalkyl phosphate
  • Secondary aliphatic/aromatic amine
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Pyrimidine
  • Alkyl phosphate
  • Heteroaromatic compound
  • Vinylogous amide
  • Ketimine
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Secondary amine
  • Primary amine
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Organic nitrogen compound
  • Imine
  • 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 Solubility4.13 g/LALOGPS
logP-1.4ALOGPS
logP-2.6ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)1.78ChemAxon
pKa (Strongest Basic)0.43ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area205.16 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity79.6 m³·mol⁻¹ChemAxon
Polarizability27.51 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • mitochondrion
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG Pathways
Folate biosynthesisec00790 Map00790
SMPDB ReactionsNot Available
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
(2-Amino-4-hydroxy-7,8-dihydropteridin-6-yl)methyl trihydrogen diphosphate + 4-Aminobenzoic acid → Pyrophosphate + 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, Positivesplash10-002b-9721000000-7dd8d7f2621d27bc6a60JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0923000000-daae4676a03d5a81c9dcJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0910000000-fbe617240fb10e7d245cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0059-0900000000-8213899ab549e9639b96JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ufr-0509000000-6652a04120c6b6728e11JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-057i-9802000000-be3aa50bfc0d700c94b5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-3071a16345027172ac91JSpectraViewer
References
References:
  • 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
  • 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
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID15998
HMDB IDNot Available
Pubchem Compound ID666
Kegg IDC04807
ChemSpider ID646
FOODB IDNot Available
Wikipedia ID2-Amino-4-hydroxy-6-pyrophosphoryl-methylpteridine
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.