Record Information
Version2.0
Creation Date2012-07-30 14:54:47 -0600
Update Date2015-06-03 17:20:49 -0600
Secondary Accession Numbers
  • ECMDB21182
Identification
Name:6-Hydroxymethyl-dihydropterin pyrophosphate
Description6-hydroxymethyl-dihydropterin pyrophosphate 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.
Structure
Thumb
Synonyms:
  • (2-amino-4-hydroxy-7,8-dihydropteridin-6-yl)methyl diphosphate
  • (2-amino-4-Hydroxy-7,8-dihydropteridin-6-yl)methyl diphosphoric acid
  • 2-Amino-7,8-dihydro-4-hydroxy-6-(diphosphooxymethyl)-pteridine
  • 6-hydroxymethyl-dihydropterin pyrophosphate
  • 6-Hydroxymethyl-dihydropterin pyrophosphoric acid
  • AHHMeDHPDP
  • Dihydropterin-CH2OH-diphosphate
  • Dihydropterin-CH2OH-diphosphoric acid
  • Dihydropterin-CH2OH-pp
Chemical Formula:C7H8N5O8P2
Weight:Average: 352.1146
Monoisotopic: 351.984810281
InChI Key:FCQGJGLSOWZZON-UHFFFAOYSA-K
InChI:InChI=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)/p-3
CAS number:Not Available
IUPAC Name:6-({[hydroxy(phosphonatooxy)phosphoryl]oxy}methyl)-2-imino-1,2,7,8-tetrahydropteridin-4-olate
Traditional IUPAC Name:6-({[hydroxy(phosphonatooxy)phosphoryl]oxy}methyl)-2-imino-7,8-dihydro-1H-pteridin-4-olate
SMILES:OP(=O)(OCC1=NC2=C(NC1)NC(=N)N=C2[O-])OP([O-])([O-])=O
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
  • Secondary aliphatic/aromatic amine
  • Organic phosphoric acid derivative
  • Alkyl phosphate
  • Phosphoric acid ester
  • Pyrimidine
  • Heteroaromatic compound
  • Vinylogous amide
  • Ketimine
  • Azacycle
  • Secondary amine
  • Organic oxygen compound
  • Primary amine
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Imine
  • Hydrocarbon derivative
  • Amine
  • Organic anion
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility5.96 g/LALOGPS
logP-1.1ALOGPS
logP-5.1ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)-13ChemAxon
pKa (Strongest Basic)15ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area214.64 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity98.72 m³·mol⁻¹ChemAxon
Polarizability26.84 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Folate biosynthesisPW000908 ThumbThumb?image type=greyscaleThumb?image type=simple
GTP degradationPW001888 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
  • 6-hydroxymethyl-dihydropterin diphosphate biosynthesis I PWY-6147
  • tetrahydrofolate biosynthesis PWY-6614
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0109000000-1f3ef2d80c56c29be322View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f80-1395000000-b45ccdcb2650ad3a87a9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00s9-2902000000-b7225329cfc74c11ce58View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-305d5337ac5a5e4e3363View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-4109000000-40e6973cdf8f0452ce7bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-003s-9000000000-4020cd351b1c6a49b0b3View in MoNA
References
References:
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID57602
HMDB IDNot Available
Pubchem Compound ID25244074
Kegg IDC04807
ChemSpider ID24784870
Wikipedia IDNot Available
BioCyc IDDIHYDROPTERIN-CH2OH-PP
EcoCyc IDDIHYDROPTERIN-CH2OH-PP

Enzymes

General function:
Involved in dihydropteroate synthase activity
Specific function:
DHPS catalyzes the formation of the immediate precursor of folic acid. It is implicated in resistance to sulfonamide
Gene Name:
folP
Uniprot ID:
P0AC13
Molecular weight:
30615
Reactions
(2-amino-4-hydroxy-7,8-dihydropteridin-6-yl)methyl diphosphate + 4-aminobenzoate = diphosphate + dihydropteroate.
General function:
Involved in 2-amino-4-hydroxy-6-hydroxymethyldihydropteridine diphosphokinase activity
Specific function:
ATP + 2-amino-4-hydroxy-6-hydroxymethyl-7,8- dihydropteridine = AMP + (2-amino-4-hydroxy-7,8-dihydropteridin-6- yl)methyl diphosphate
Gene Name:
folK
Uniprot ID:
P26281
Molecular weight:
18079
Reactions
ATP + 2-amino-4-hydroxy-6-hydroxymethyl-7,8-dihydropteridine = AMP + (2-amino-4-hydroxy-7,8-dihydropteridin-6-yl)methyl diphosphate.