Showing metabocard for Dihydroneopterin triphosphate (BMDB0000980)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (3) Show 3 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:39:25 UTC
Update Date2020-05-21 16:29:04 UTC
BMDB IDBMDB0000980
Secondary Accession Numbers
  • BMDB00980
Metabolite Identification
Common NameDihydroneopterin triphosphate
DescriptionDihydroneopterin triphosphate 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. Dihydroneopterin triphosphate exists in all living species, ranging from bacteria to plants to humans. Based on a literature review a significant number of articles have been published on Dihydroneopterin triphosphate.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-Amino-4-hydroxy-6-(erythro-1,2,3-trihydroxypropyl)dihydropteridine triphosphateChEBI
6-(L-Erythro-1,2-dihydroxy-3-triphosphooxypropyl)-7,8-dihydropterinChEBI
6-(L-Erythro-1,2-dihydroxypropyl 3-triphosphate)-7,8-dihydropterinChEBI
6-[(1S,2R)-1,2-Dihydroxy-3-triphosphooxypropyl]-7,8-dihydropterinChEBI
2-Amino-4-hydroxy-6-(erythro-1,2,3-trihydroxypropyl)dihydropteridine triphosphoric acidGenerator
6-(L-Erythro-1,2-dihydroxypropyl 3-triphosphoric acid)-7,8-dihydropterinGenerator
Dihydroneopterin triphosphoric acidGenerator
2-amino-4-Hydroxy-6-(erythro-1,2,3-trihydroxypropyl) dihydropteridine triphosphateHMDB
7,8-Dihydroneopterin 3'-triphosphateHMDB
7,8-Dihydroneopterin triphosphateHMDB
Dihydroneopterin triphosphate, (S-(r*,s*))-isomerMeSH, HMDB
dihydro-Neopterin triphosphateMeSH, HMDB
Dihydroneopterin triphosphateHMDB
Chemical FormulaC9H16N5O13P3
Average Molecular Weight495.1703
Monoisotopic Molecular Weight494.995745159
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 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
CAS Registry Number20574-65-6
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
InChI Identifier
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
InChI KeyDGGUVLXVLHAAGT-XINAWCOVSA-N
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
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0000980
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022349
KNApSAcK IDC00007510
Chemspider ID108735
KEGG Compound IDC04895
BioCyc IDDIHYDRONEOPTERIN-P3
BiGG ID44843
Wikipedia Link7,8-Dihydroneopterin triphosphate
METLIN ID5917
PubChem Compound121885
PDB IDNot Available
ChEBI ID18372
References
Synthesis ReferenceFerre, 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
General ReferencesNot Available

Enzymes

Enzyme Details
1. GTP cyclohydrolase 1 feedback regulatory protein
General function:
Involved in protein binding
Specific function:
Mediates tetrahydrobiopterin inhibition of GTP cyclohydrolase 1. This inhibition is reversed by L-phenylalanine (By similarity).
Gene Name:
GCHFR
Uniprot ID:
Q32L41
Molecular weight:
9557.0
Reactions
2,5-Diamino-6-(5'-triphosphoryl-3',4'-trihydroxy-2'-oxopentyl)-amino-4-oxopyrimidine → Dihydroneopterin triphosphate + Waterdetails
Enzyme Details
2. GTP cyclohydrolase 1
General function:
Not Available
Specific function:
Not Available
Gene Name:
GCH1
Uniprot ID:
F1MZ14
Molecular weight:
27726.0
Reactions
2,5-Diamino-6-(5'-triphosphoryl-3',4'-trihydroxy-2'-oxopentyl)-amino-4-oxopyrimidine → Dihydroneopterin triphosphate + Waterdetails
Enzyme Details
3. 6-pyruvoyl tetrahydrobiopterin synthase
General function:
Not Available
Specific function:
Not Available
Gene Name:
PTS
Uniprot ID:
F1MX94
Molecular weight:
16363.0
Reactions
Dihydroneopterin triphosphate → Dyspropterin + Triphosphatedetails