Dihydromonapterin-triphosphate (ECMDB20549) (M2MDB001355)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (1)XML
Proteins (1)
Record Information
Version2.0
Creation Date2012-05-31 14:50:09 -0600
Update Date2015-06-03 17:20:12 -0600
Secondary Accession Numbers
  • ECMDB20549
Identification
Name:Dihydromonapterin-triphosphate
DescriptionDihydromonapterin-triphosphate is a member of the chemical class known as Biopterins and Derivatives. These are coenzymes containing a 2-amino-pteridine-4-one derivative. 7,8-Dihydroneopterin triphosphate (DHNTP) is an intermediate in tetrahydrobiopterin and tetrahydromonopterin biosynthesis. Tetrahydromonapterin is the major tetrahydropterin in E. coli, although the biological role of tetrahydromonapterin in E. coli is currently unknown.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • 6-(L-threo-1',2',3'-trihydroxypropyl)-7,8-dihydropterin-3'-triphosphate
  • 6-(L-Threo-1',2',3'-trihydroxypropyl)-7,8-dihydropterin-3'-triphosphate
  • 6-(L-Threo-1',2',3'-trihydroxypropyl)-7,8-dihydropterin-3'-triphosphoric acid
  • 6-(L-threo-1',2',3'-Trihydroxypropyl)-7,8-dihydropterin-3'-triphosphoric acid
  • Dihydromonapterin-triphosphate
  • Dihydromonapterin-triphosphoric acid
  • H2MTP
  • H2MTP
Chemical Formula:C9H14N5O13P3
Weight:Average: 493.1544
Monoisotopic: 492.980095095
InChI Key:FXEIKSFXDSWHMF-NJGYIYPDSA-N
InChI:InChI=1S/C9H14N5O13P3/c10-9-13-7-5(8(17)14-9)12-3(1-11-7)6(16)4(15)2-25-29(21,22)27-30(23,24)26-28(18,19)20/h4,6,15-16H,1-2H2,(H6-,10,11,13,14,17,18,19,20,21,22,23,24)/q+1/t4-,6-/m0/s1
CAS number:Not Available
IUPAC Name:6-[(1S,2S)-3-[({[(hydrogen phosphonatooxy)phosphinato]oxy}phosphinato)-λ³-oxidanyliumyl]-1,2-dihydroxypropyl]-4-hydroxy-2-iminiumyl-2,7-dihydro-1H-5λ⁵-pteridin-8-ium-5-ylium
Traditional IUPAC Name:6-[(1S,2S)-3-{[(hydrogen phosphonatooxyphosphinato)oxyphosphinato]-λ³-oxidanyliumyl}-1,2-dihydroxypropyl]-4-hydroxy-2-iminio-1,7-dihydro-5λ⁵-pteridin-8-ium-5-ylium
SMILES:[H][C@](O)(C[O+]P([O-])(=O)OP([O-])(=O)O[P+](O)([O-])[O-])[C@@]([H])(O)C1=[N+]=C2C(O)=NC(=[NH2+])NC2=[NH+]C1
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
  • Organic pyrophosphate
  • Hydroxypyrimidine
  • Alkyl phosphate
  • Pyrimidine
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Heteroaromatic compound
  • Secondary alcohol
  • 1,2-diol
  • Azacycle
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
State:Not Available
Charge:0
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility12.9 g/LALOGPS
logP1.29ALOGPS
logP-9.2ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)-12ChemAxon
pKa (Strongest Basic)15.21ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area298.94 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity121.55 m³·mol⁻¹ChemAxon
Polarizability37.69 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Dihydroneopterin triphosphate <> Dihydromonapterin-triphosphate
Dihydromonapterin-triphosphate + Water > Hydrogen ion + 7,8-Dihydroneopterin + Phosphate
7,8-dihydroneopterin 3'-triphosphate <> Dihydromonapterin-triphosphate
SMPDB Pathways:
Tetrahydromonapterin BiosynthesisPW002043 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:Not Available
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
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
  • 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 IDNot Available
HMDB IDNot Available
Pubchem Compound ID25203084
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDDIHYDROMONAPTERIN-TRIPHOSPHATE
EcoCyc IDDIHYDROMONAPTERIN-TRIPHOSPHATE

Enzymes

Protein Details
1. D-erythro-7,8-dihydroneopterin triphosphate epimerase
General function:
Involved in dihydroneopterin aldolase activity
Specific function:
Catalyzes the epimerization of carbon 2' of the side chain of dihydroneopterin triphosphate (H2NTP) to form dihydromonapterin triphosphate (H2MTP)
Gene Name:
folX
Uniprot ID:
P0AC19
Molecular weight:
14082
Reactions
D-erythro-7,8-dihydroneopterin triphosphate = L-threo-7,8-dihydroneopterin triphosphate.