P. aeruginosa Metabolome Database: Dihydroneopterin triphosphate (PAMDB000274)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 11:54:54 AM

Metabolite ID

PAMDB000274

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 View Structure

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

Average Molecular Weight:

495.1703

Monoisotopic Molecular Weight:

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-3,4,7,8-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-3H-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

Taxonomy Description

This compound 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
Organic pyrophosphate
Monoalkyl phosphate
Secondary aliphatic/aromatic amine
Pyrimidone
Imidolactam
Alkyl phosphate
Pyrimidine
Primary aromatic amine
Phosphoric acid ester
Organic phosphoric acid derivative
Organic phosphate
Heteroaromatic compound
Vinylogous amide
Secondary alcohol
Lactam
Ketimine
1,2-diol
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Secondary amine
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Imine
Amine
Alcohol
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	6.62 mg/mL	ALOGPS
logP	-0.77	ALOGPS
logP	-4.5	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	0.89	ChemAxon
pKa (Strongest Basic)	3.68	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	292.15 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	102.48 m³·mol^-1	ChemAxon
Polarizability	36.75 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:

Pathways:

Folate biosynthesis pae00790
Metabolic pathways pae01100

Spectra

Spectra:

Spectrum Type	Description	Splash Key
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

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	Not Available
BioCyc ID	DIHYDRONEOPTERIN-P3
EcoCyc ID	DIHYDRONEOPTERIN-P3

Dihydroneopterin triphosphate (PAMDB000274)

Structure for Dihydroneopterin triphosphate (PAMDB000274)