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Record Information

Version

2.0

Creation Date

2012-08-09 09:16:17 -0600

Update Date

2015-06-03 17:21:32 -0600

Secondary Accession Numbers

ECMDB21452

Identification

Name:

Dihydroneopterin phosphate

Description

Dihydroneopterin phosphate is involved in the folate biosynthesis pathway. Dihydroneopterin phosphate is produced from 2-Amino-4-hydroxy-6-(erythro-1,2,3-trihydroxypropyl)dihydropteridine triphosphate by [E3.6.1.-] or nudB in E. coli. Dihydroneopterin phosphate is then converted to Dihydroneopterin by [E3.6.1.-].

Structure

MOL SDF PDB SMILES InChI

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
DHNPMP
Dihydroneopterin 3'-monophosphate
Dihydroneopterin 3'-monophosphoric acid
Dihydroneopterin 3'-phosphate
Dihydroneopterin 3'-phosphoric acid
Dihydroneopterin phosphoric acid
Dihydroneopterin-P

Chemical Formula:

C₉H₁₄N₅O₇P

Weight:

Average: 335.2105
Monoisotopic: 335.063084339

InChI Key:

PLSQMGZYOGSOCE-XINAWCOVSA-N

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)/t4-,6+/m1/s1

CAS number:

Not Available

IUPAC Name:

[(2R,3S)-3-(2-amino-4-oxo-1,4,7,8-tetrahydropteridin-6-yl)-2,3-dihydroxypropoxy]phosphonic acid

Traditional IUPAC Name:

(2R,3S)-3-(2-amino-4-oxo-7,8-dihydro-1H-pteridin-6-yl)-2,3-dihydroxypropoxyphosphonic acid

SMILES:

NC1=NC2=C(N=C(CN2)[C@H](O)[C@H](O)COP(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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pteridines and derivatives

Sub Class

Pterins and derivatives

Direct Parent

Biopterins and derivatives

Alternative Parents

Substituents

Biopterin
Aminopyrimidine
Pyrimidone
Secondary aliphatic/aromatic amine
Monoalkyl phosphate
Organic phosphoric acid derivative
Phosphoric acid ester
Pyrimidine
Alkyl phosphate
Heteroaromatic compound
Vinylogous amide
1,2-diol
Ketimine
Secondary alcohol
Azacycle
Organic 1,3-dipolar compound
Secondary amine
Propargyl-type 1,3-dipolar organic compound
Amine
Hydrocarbon derivative
Primary amine
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Alcohol
Imine
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

pterin phosphate (CHEBI:48954 )
dihydropterin (CHEBI:48954 )
neopterins (CHEBI:48954 )

Physical Properties

State:

Solid

Charge:

-2

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	5.26 g/L	ALOGPS
logP	-2.3	ALOGPS
logP	-3.6	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	1.51	ChemAxon
pKa (Strongest Basic)	0.18	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	199.09 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	80.53 m³·mol⁻¹	ChemAxon
Polarizability	28.71 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

SMPDB Pathways:

Not Available

KEGG Pathways:

Not Available

EcoCyc Pathways:

Not Available

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0005-8911000000-53dc19c24dbe99c4297c	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-03dj-9412400000-711e5bff9c050e651d6f	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-1149000000-5fbd207fae24db394e97	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01p9-3984000000-b1316677bed07bd7f55d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03ka-1910000000-4900a3a0b1a8c45967d0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-003u-6519000000-d97b00fd24549be11a57	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9200000000-17032e05ed4e9517e10d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-767fc48b2593a3849c9a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0049000000-34ddec995961538a2b69	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00dr-0093000000-9db5d730be4336945735	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-1910000000-fbf02f9608828a708ae3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-003r-9008000000-046b0ad106139a51dfcc	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000000000-a3ddbffe59a79724cf9e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9100000000-3e79dacf1a5decbc02d9	View in MoNA
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer

References

References:

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

Links

External Links:

Resource	Link
CHEBI ID	48954
HMDB ID	HMDB06824
Pubchem Compound ID	24771767
Kegg ID	C05925
ChemSpider ID	21865614
Wikipedia ID	Not Available
BioCyc ID	Not Available

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

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Dihydroneopterin phosphate (M2MDB001847)

Structure for #<Compound:0xae8604a8>

Enzymes