(2-amino-4-hydroxy-7,8-dihydropteridin-6-yl)methyl diphosphate(3-) (YMDB00356)

Identification
YMDB IDYMDB00356
Name(2-amino-4-hydroxy-7,8-dihydropteridin-6-yl)methyl diphosphate(3-)
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description(2-Amino-4-hydroxy-7,8-dihydropteridin-6-yl)methyl diphosphate(3-) is an intermediate in the tetrahydrofolate biosynthesis pathway. Tetrahydrofolate (vitamin B9) is the parent structure of the large family of folates coenzymes. Folates are essential cofactors that facilitate the transfer of one-carbon units from donor molecules into important biosynthetic pathways leading to methionine, purine, and pyrimidine biosynthesis. [Biocyc PWY-6614]
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • (2-amino-4-hydroxy-7,8-dihydropteridin-6-yl)methyl diphosphate trianion
  • 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 numberNot Available
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=NC(O)=C2N=C(COP(O)(=O)OP(O)(O)=O)CNC2=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 LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
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:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
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.