7,8-dihydroneopterin 3'-triphosphate (ECMDB24245) (M2MDB006362)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (4)XML
Proteins (4)
Record Information
Version2.0
Creation Date2015-09-08 17:50:23 -0600
Update Date2015-09-14 16:46:03 -0600
Secondary Accession Numbers
  • ECMDB24245
Identification
Name:7,8-dihydroneopterin 3'-triphosphate
Description7,8-dihydroneopterin 3'-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
MOLSDFPDBSMILESInChI
Synonyms:
  • 7,8-Dihydroneopterin 3'-triphosphoric acid
Chemical Formula:C9H12N5O13P3
Weight:Average: 491.14
Monoisotopic: 490.96664078
InChI Key:DGGUVLXVLHAAGT-UHFFFAOYSA-J
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)/p-4
CAS number:Not Available
IUPAC Name:{[3-(2-amino-4-oxo-1,4,7,8-tetrahydropteridin-6-yl)-2,3-dihydroxypropyl phosphonato]oxy}(phosphonatooxy)phosphinate
Traditional IUPAC Name:[3-(2-amino-4-oxo-7,8-dihydro-1H-pteridin-6-yl)-2,3-dihydroxypropyl phosphonato]oxy(phosphonatooxy)phosphinate
SMILES:NC1=NC(=O)C2=C(NCC(=N2)C(O)C(O)COP([O-])(=O)OP([O-])(=O)OP([O-])([O-])=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
  • Secondary aliphatic/aromatic amine
  • Pyrimidone
  • Organic phosphoric acid derivative
  • Alkyl phosphate
  • Pyrimidine
  • Phosphoric acid ester
  • Heteroaromatic compound
  • Vinylogous amide
  • 1,2-diol
  • Ketimine
  • Secondary alcohol
  • Azacycle
  • Secondary amine
  • Organic nitrogen compound
  • Alcohol
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Imine
  • Organic oxide
  • Organic oxygen compound
  • Amine
  • Organic anion
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-3
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility20.2 g/LALOGPS
logP-0.91ALOGPS
logP-4.3ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)0.9ChemAxon
pKa (Strongest Basic)-1.5ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area303.47 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity97.79 m³·mol⁻¹ChemAxon
Polarizability36.25 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Guanosine triphosphate + Water > Formic acid + Hydrogen ion + 7,8-dihydroneopterin 3'-triphosphate
7,8-dihydroneopterin 3'-triphosphate + Water > Pyrophosphate + Hydrogen ion + Dihydroneopterin monophosphate
7,8-dihydroneopterin 3'-triphosphate + Water > Acetaldehyde + Triphosphate +2 Hydrogen ion + 6-Carboxy-5,6,7,8-tetrahydropterin + Triphosphate
7,8-dihydroneopterin 3'-triphosphate <> Dihydromonapterin-triphosphate
SMPDB Pathways:
Folate biosynthesisPW000908 ThumbThumb?image type=greyscaleThumb?image type=simple
GTP degradationPW001888 ThumbThumb?image type=greyscaleThumb?image type=simple
Tetrahydromonapterin BiosynthesisPW002043 ThumbThumb?image type=greyscaleThumb?image type=simple
preQ0 metabolismPW001893 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000900000-8a545d680f1756e38c23View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01xx-0000900000-2766c5258dab230a190dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0feb-7793400000-594351870587bdb6b15bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000900000-f7c6c00ca0a678229441View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000f-4100900000-04d9785e596e41bd3d38View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01si-9600000000-23b7f89c2bd7b56c798aView in MoNA
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDNot Available
Pubchem Compound ID57376516
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. GTP cyclohydrolase 1
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.
Protein Details
2. 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.
Protein Details
3. 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
4. 6-carboxy-5,6,7,8-tetrahydropterin synthase
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.