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Record Information
Version2.0
Creation Date2012-08-09 09:16:17 -0600
Update Date2015-06-03 17:21:32 -0600
Secondary Accession Numbers
  • ECMDB21452
Identification
Name:Dihydroneopterin phosphate
DescriptionDihydroneopterin phosphate is involved in the folate biosynthesis pathway. Dihydroneopterin phosphate is produced from 2-Amino-4-hydroxy-6-(erythro-1,2,3-trihydroxypropyl)dihydropteridine triphosphate by [E3.6.1.-] or nudB in E. coli. Dihydroneopterin phosphate is then converted to Dihydroneopterin by [E3.6.1.-].
Structure
Thumb
Synonyms:
  • 2-Amino-4-hydroxy-6-(erythro-1,2,3-trihydroxypropyl)dihydropteridine phosphate
  • 2-amino-4-Hydroxy-6-(erythro-1,2,3-trihydroxypropyl)dihydropteridine phosphoric acid
  • 7,8-Dihydro-D-neopterin 3'-phosphate
  • 7,8-dihydro-D-Neopterin 3'-phosphoric acid
  • DHNPMP
  • Dihydroneopterin 3'-monophosphate
  • Dihydroneopterin 3'-monophosphoric acid
  • Dihydroneopterin 3'-phosphate
  • Dihydroneopterin 3'-phosphoric acid
  • Dihydroneopterin phosphoric acid
  • Dihydroneopterin-P
Chemical Formula:C9H14N5O7P
Weight:Average: 335.2105
Monoisotopic: 335.063084339
InChI Key:PLSQMGZYOGSOCE-XINAWCOVSA-N
InChI:InChI=1S/C9H14N5O7P/c10-9-13-7-5(8(17)14-9)12-3(1-11-7)6(16)4(15)2-21-22(18,19)20/h4,6,15-16H,1-2H2,(H2,18,19,20)(H4,10,11,13,14,17)/t4-,6+/m1/s1
CAS number:Not Available
IUPAC Name:[(2R,3S)-3-(2-amino-4-oxo-1,4,7,8-tetrahydropteridin-6-yl)-2,3-dihydroxypropoxy]phosphonic acid
Traditional IUPAC Name:(2R,3S)-3-(2-amino-4-oxo-7,8-dihydro-1H-pteridin-6-yl)-2,3-dihydroxypropoxyphosphonic acid
SMILES:NC1=NC2=C(N=C(CN2)[C@H](O)[C@H](O)COP(O)(O)=O)C(=O)N1
Chemical Taxonomy
Description belongs to the class of organic compounds known as biopterins and derivatives. These are coenzymes containing a 2-amino-pteridine-4-one derivative. They are mainly synthesized in several parts of the body, including the pineal gland.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPteridines and derivatives
Sub ClassPterins and derivatives
Direct ParentBiopterins and derivatives
Alternative Parents
Substituents
  • Biopterin
  • Aminopyrimidine
  • Pyrimidone
  • Secondary aliphatic/aromatic amine
  • Monoalkyl phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Pyrimidine
  • Alkyl phosphate
  • Heteroaromatic compound
  • Vinylogous amide
  • 1,2-diol
  • Ketimine
  • Secondary alcohol
  • Azacycle
  • Organic 1,3-dipolar compound
  • Secondary amine
  • Propargyl-type 1,3-dipolar organic compound
  • Amine
  • Hydrocarbon derivative
  • Primary amine
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Alcohol
  • Imine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility5.26 g/LALOGPS
logP-2.3ALOGPS
logP-3.6ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)1.51ChemAxon
pKa (Strongest Basic)0.18ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area199.09 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity80.53 m³·mol⁻¹ChemAxon
Polarizability28.71 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0005-8911000000-53dc19c24dbe99c4297cView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-03dj-9412400000-711e5bff9c050e651d6fView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1149000000-5fbd207fae24db394e97View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01p9-3984000000-b1316677bed07bd7f55dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03ka-1910000000-4900a3a0b1a8c45967d0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-003u-6519000000-d97b00fd24549be11a57View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9200000000-17032e05ed4e9517e10dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-767fc48b2593a3849c9aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0049000000-34ddec995961538a2b69View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dr-0093000000-9db5d730be4336945735View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-1910000000-fbf02f9608828a708ae3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-003r-9008000000-046b0ad106139a51dfccView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-a3ddbffe59a79724cf9eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9100000000-3e79dacf1a5decbc02d9View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID48954
HMDB IDHMDB06824
Pubchem Compound ID24771767
Kegg IDC05925
ChemSpider ID21865614
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

General function:
Involved in dATP pyrophosphohydrolase activity
Specific function:
Catalyzes the hydrolysis of dihydroneopterin triphosphate to dihydroneopterin monophosphate and pyrophosphate. Required for efficient folate biosynthesis. Can also hydrolyze nucleoside triphosphates with a preference for dATP
Gene Name:
nudB
Uniprot ID:
P0AFC0
Molecular weight:
17306