Record Information
Version2.0
Creation Date2012-05-31 13:46:20 -0600
Update Date2015-06-03 15:53:47 -0600
Secondary Accession Numbers
  • ECMDB01144
Identification
Name:Dihydroneopterin triphosphate
Description7,8-Dihydroneopterin triphosphate (DHNTP) is an intermediate in folate biosynthesis. It is converted from 2,5-Diamino-6-(5'-triphosphoryl-3',4'-trihydroxy-2'-oxopentyl)-amino-4-oxopyrimidine by dihydroneopterin triphosphate synthase (EC:3.5.4.16) (KEGG)
Structure
Thumb
Synonyms:
  • 2-amino-4-hydroxy-6-(erythro-1,2,3-trihydroxypropyl)dihydropteridine triphosphate
  • 2-Amino-4-hydroxy-6-(erythro-1,2,3-trihydroxypropyl) dihydropteridine triphosphate
  • 2-amino-4-Hydroxy-6-(erythro-1,2,3-trihydroxypropyl) dihydropteridine triphosphoric acid
  • 2-Amino-4-hydroxy-6-(erythro-1,2,3-trihydroxypropyl)dihydropteridine triphosphate
  • 2-amino-4-Hydroxy-6-(erythro-1,2,3-trihydroxypropyl)dihydropteridine triphosphoric acid
  • 6-(D-erythro-1',2',3'-trihydroxypropyl)-7,8-dihydropterin-3'-triphosphate
  • 6-(D-Erythro-1',2',3'-trihydroxypropyl)-7,8-dihydropterin-3'-triphosphate
  • 6-(D-Erythro-1',2',3'-trihydroxypropyl)-7,8-dihydropterin-3'-triphosphoric acid
  • 6-(D-erythro-1',2',3'-Trihydroxypropyl)-7,8-dihydropterin-3'-triphosphoric acid
  • 6-(L-Erythro-1,2-Dihydroxypropyl 3-triphosphate)-7,8-dihydropterin
  • 6-(L-erythro-1,2-Dihydroxypropyl 3-triphosphoric acid)-7,8-dihydropterin
  • 6-[(1S,2R)-1,2-Dihydroxy-3-triphosphooxypropyl]-7,8-dihydropterin
  • 7,8-Dihydroneopterin 3'-triphosphate
  • 7,8-Dihydroneopterin 3'-triphosphoric acid
  • 7,8-Dihydroneopterin triphosphate
  • 7,8-Dihydroneopterin triphosphoric acid
  • D-Erythro-7,8-dihydroneopterin triphosphate
  • D-erythro-7,8-Dihydroneopterin triphosphoric acid
  • DHNPTP
  • Dihydroneopterin triphosphate
  • Dihydroneopterin triphosphoric acid
  • H2NTP
  • H2NTP
Chemical Formula:C9H16N5O13P3
Weight:Average: 495.1703
Monoisotopic: 494.995745159
InChI Key:DGGUVLXVLHAAGT-XINAWCOVSA-N
InChI:InChI=1S/C9H16N5O13P3/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,(H,21,22)(H,23,24)(H2,18,19,20)(H4,10,11,13,14,17)/t4-,6+/m1/s1
CAS number:20574-65-6
IUPAC Name:{[({[(2R,3S)-3-(2-amino-4-oxo-1,4,7,8-tetrahydropteridin-6-yl)-2,3-dihydroxypropoxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}phosphonic acid
Traditional IUPAC Name:{[(2R,3S)-3-(2-amino-4-oxo-7,8-dihydro-1H-pteridin-6-yl)-2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy(hydroxy)phosphoryl}oxyphosphonic acid
SMILES:NC1=NC2=C(N=C(CN2)[C@H](O)[C@H](O)COP(O)(=O)OP(O)(=O)OP(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
  • Hydroxypyrimidine
  • Secondary aliphatic/aromatic amine
  • Monoalkyl phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Pyrimidine
  • Alkyl phosphate
  • Heteroaromatic compound
  • 1,2-diol
  • Ketimine
  • Secondary alcohol
  • Secondary amine
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Hydrocarbon derivative
  • Amine
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Alcohol
  • Imine
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-3
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility6.43 g/LALOGPS
logP-0.71ALOGPS
logP-4.3ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)0.9ChemAxon
pKa (Strongest Basic)-1.5ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area292.15 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity102.28 m³·mol⁻¹ChemAxon
Polarizability37.74 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
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0kdm-5895400000-c878c84180ac32db5d6eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00fs-7239235000-209a5180925a00469a6fView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_8) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_13) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_14) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-1344900000-749ef2751d4c02be068cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03ds-3966200000-7b11e054b0d9f45b441dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-1920000000-db4d3283e1adc21eb602View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0430900000-3810f529876f3b2a139cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-005c-9550100000-5ca0214d149cdaf8e715View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-9610000000-4ef866d42ea41abade0fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0000900000-c66663d87526f1b932c8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00ks-0049600000-b0bd4a1239d964cfabc2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000b-0931000000-e97653fab66aeb2aeb35View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0100900000-44d989804f7de0829af1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-8501900000-f10d33df2b148966d71fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-e1f5b79920ef4f1ff109View 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:
  • Curtius HC, Heintel D, Ghisla S, Kuster T, Leimbacher W, Niederwieser A: Biosynthesis of tetrahydrobiopterin in man. J Inherit Metab Dis. 1985;8 Suppl 1:28-33. Pubmed: 3930838
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • 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:Ferre, Juan; Naylor, Edwin W.; Jacobson, K. Bruce. Repetitive recycling of guanosine triphosphate cyclohydrolase I for synthesis of dihydroneopterin triphosphate. Analytical Biochemistry (1989), 176(1), 15-18.
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID18372
HMDB IDHMDB00980
Pubchem Compound ID121885
Kegg IDC04895
ChemSpider ID108735
Wikipedia ID7,8-Dihydroneopterin triphosphate
BioCyc IDDIHYDRONEOPTERIN-P3
EcoCyc IDDIHYDRONEOPTERIN-P3

Enzymes

General function:
Involved in catalytic activity
Specific function:
A phosphate monoester + H(2)O = an alcohol + phosphate
Gene Name:
phoA
Uniprot ID:
P00634
Molecular weight:
49438
Reactions
A phosphate monoester + H(2)O = an alcohol + phosphate.
General function:
Involved in GTP cyclohydrolase I activity
Specific function:
GTP + H(2)O = formate + 2-amino-4-hydroxy-6- (erythro-1,2,3-trihydroxypropyl)-dihydropteridine triphosphate
Gene Name:
folE
Uniprot ID:
P0A6T5
Molecular weight:
24830
Reactions
GTP + H(2)O = formate + 2-amino-4-hydroxy-6-(erythro-1,2,3-trihydroxypropyl)-dihydropteridine triphosphate.
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.
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
General function:
Coenzyme transport and metabolism
Specific function:
Catalyzes the conversion of 7,8-dihydroneopterin triphosphate (H2NTP) to 6-carboxy-5,6,7,8-tetrahydropterin (CPH4) and acetaldehyde. Can also convert 6-pyruvoyltetrahydropterin (PPH4) and sepiapterin to CPH4; these 2 compounds are probably intermediates in the reaction from H2NTP
Gene Name:
queD
Uniprot ID:
P65870
Molecular weight:
13773
Reactions
7,8-dihydroneopterin 3'-triphosphate + H(2)O = 6-carboxy-5,6,7,8-tetrahydropterin + acetaldehyde + triphosphate.
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.