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Dihydroneopterin monophosphate (M2MDB001614)

Record Information
Version2.0
Creation Date2012-07-30 14:54:55 -0600
Update Date2015-06-03 17:20:52 -0600
Secondary Accession Numbers
  • ECMDB21206
Identification
Name:Dihydroneopterin monophosphate
DescriptionDihydroneopterin monophosphate is a member of the chemical class known as Biopterins and Derivatives. These are coenzymes containing a 2-amino-pteridine-4-one derivative. Dihdroneopterin monophosphate is an intermediate involved in tetrahydrofolate biosynthesis and salvage in E. coli. It is converted to 7,8-dihydroneopterin through an unknown phosphorylase enzyme.
Structure
Thumb
MOLSDFPDBSMILESInChI
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
  • Dihydroneopterin 3'-monophosphate
  • Dihydroneopterin 3'-monophosphoric acid
  • Dihydroneopterin 3'-phosphate
  • Dihydroneopterin 3'-phosphoric acid
  • Dihydroneopterin monophosphoric acid
  • Dihydroneopterin-P
Chemical Formula:C9H12N5O7P
Weight:Average: 333.1946
Monoisotopic: 333.047434275
InChI Key:PLSQMGZYOGSOCE-XINAWCOVSA-L
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)/p-2/t4-,6+/m1/s1
CAS number:Not Available
IUPAC Name:6-[(1S,2R)-3-(hydrogen phosphonatooxy)-1,2-dihydroxypropyl]-2-imino-1,2,7,8-tetrahydropteridin-4-olate
Traditional IUPAC Name:6-[(1S,2R)-3-(hydrogen phosphonatooxy)-1,2-dihydroxypropyl]-2-imino-7,8-dihydro-1H-pteridin-4-olate
SMILES:[H][C@@](O)(COP(O)([O-])=O)[C@@]([H])(O)C1=NC2=C(NC1)NC(=N)N=C2[O-]
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
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Pyrimidine
  • Alkyl phosphate
  • Heteroaromatic compound
  • Vinylogous amide
  • 1,2-diol
  • Ketimine
  • Secondary alcohol
  • Azacycle
  • Secondary amine
  • Hydrocarbon derivative
  • Primary amine
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Alcohol
  • Imine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Amine
  • Organic anion
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility3.29 g/LALOGPS
logP-1.7ALOGPS
logP-5.8ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)-13ChemAxon
pKa (Strongest Basic)15.08ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area205.74 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity100.97 m³·mol⁻¹ChemAxon
Polarizability27.1 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Dihydroneopterin triphosphate + Water > Dihydroneopterin monophosphate + Hydrogen ion + Pyrophosphate
Dihydroneopterin monophosphate + Water > 7,8-Dihydroneopterin + Phosphate
7,8-dihydroneopterin 3'-triphosphate + Water > Pyrophosphate + Hydrogen ion + Dihydroneopterin monophosphate
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
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-1009000000-35334543f830e03972d5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0032-5119000000-8a1311553ff5e2a2a732View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01qd-9741000000-f826bc486977b4d9a121View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-1009000000-a036e9146b5363f6c194View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-9002000000-60f9db77669111782949View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-003s-9000000000-116e1778470f092edb9cView in MoNA
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
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
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 ID58762
HMDB IDNot Available
Pubchem Compound ID25245170
Kegg IDC05925
ChemSpider ID26331350
Wikipedia IDNot Available
BioCyc IDDIHYDRONEOPTERIN-P
EcoCyc IDDIHYDRONEOPTERIN-P

Enzymes

Protein Details
1. Dihydroneopterin triphosphate pyrophosphatase
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
Protein Details
2. Mutator mutT protein
General function:
Replication, recombination and repair
Specific function:
Involved in the GO system responsible for removing an oxidatively damaged form of guanine (7,8-dihydro-8-oxoguanine) from DNA and the nucleotide pool. 8-oxo-dGTP is inserted opposite dA and dC residues of template DNA with almost equal efficiency thus leading to A.T to G.C transversions. MutT specifically degrades 8-oxo-dGTP to the monophosphate
Gene Name:
mutT
Uniprot ID:
P08337
Molecular weight:
14927
Reactions
8-oxo-dGTP + H(2)O = 8-oxo-dGMP + diphosphate.