ECMDB: Dihydroneopterin triphosphate (ECMDB01144) (M2MDB000274)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (6)XML

Proteins (1152)

Record Information

Version

2.0

Creation Date

2012-05-31 13:46:20 -0600

Update Date

2015-06-03 15:53:47 -0600

Secondary Accession Numbers

ECMDB01144

Identification

Name:

Dihydroneopterin triphosphate

Description

7,8-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

MOL SDF PDB SMILES InChI

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.

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
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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

pterin phosphate (CHEBI:18372 )
dihydropterin (CHEBI:18372 )
neopterins (CHEBI:18372 )

Physical Properties

State:

Solid

Charge:

-3

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	6.43 g/L	ALOGPS
logP	-0.71	ALOGPS
logP	-4.3	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	0.9	ChemAxon
pKa (Strongest Basic)	-1.5	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	292.15 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	102.28 m³·mol⁻¹	ChemAxon
Polarizability	37.74 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:

Folate biosynthesis

PW000908

KEGG Pathways:

Folate biosynthesis ec00790
Metabolic pathways eco01100

EcoCyc Pathways:

6-hydroxymethyl-dihydropterin diphosphate biosynthesis I PWY-6147
preQ₀ biosynthesis PWY-6703
tetrahydromonapterin biosynthesis PWY0-1433

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0kdm-5895400000-c878c84180ac32db5d6e	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00fs-7239235000-209a5180925a00469a6f	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_8) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_13) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_14) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-002b-1344900000-749ef2751d4c02be068c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03ds-3966200000-7b11e054b0d9f45b441d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-1920000000-db4d3283e1adc21eb602	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0430900000-3810f529876f3b2a139c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-005c-9550100000-5ca0214d149cdaf8e715	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-056r-9610000000-4ef866d42ea41abade0f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0000900000-c66663d87526f1b932c8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00ks-0049600000-b0bd4a1239d964cfabc2	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000b-0931000000-e97653fab66aeb2aeb35	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0100900000-44d989804f7de0829af1	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-8501900000-f10d33df2b148966d71f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-e1f5b79920ef4f1ff109	View in MoNA
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
1D NMR	1H NMR Spectrum	Not Available	View 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

Links

External Links:

Resource	Link
CHEBI ID	18372
HMDB ID	HMDB00980
Pubchem Compound ID	121885
Kegg ID	C04895
ChemSpider ID	108735
Wikipedia ID	7,8-Dihydroneopterin triphosphate
BioCyc ID	DIHYDRONEOPTERIN-P3
EcoCyc ID	DIHYDRONEOPTERIN-P3

Enzymes

Protein Details

1. Alkaline phosphatase

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.

Protein Details

2. 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

3. 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

4. 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

5. 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.

Protein Details

6. Mutator mutT protein

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.

Dihydroneopterin triphosphate (ECMDB01144) (M2MDB000274)

Structure for #<Compound:0x982e3bf8>

Enzymes

Reactions

Reactions

Reactions

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Reactions