P. aeruginosa Metabolome Database: Dyspropterin (PAMDB000292)

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

PAMDB000292

Identification

Name:

Dyspropterin

Description:

Dyspropterin, an intermediate formed from dihydroneopterin triphosphate in the biosynthetic pathway of tetrahydrobiopterin.

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

6-(1,2-Dioxopropyl)-5,6,7,8-tetrahydropterin
6-Pyruvoyl-5,6,7,8-tetrahydropterin
6-Pyruvoyl-tetrahydropterin
6-Pyruvoyltetrahydropterin
Dyspropterin
PPH4
Pyruvoyl-H4-pterin
Pyruvoyl-H₄-pterin

Chemical Formula:

C₉H₁₁N₅O₃

Average Molecular Weight:

237.2153

Monoisotopic Molecular Weight:

237.086189243

InChI Key:

WBJZXBUVECZHCE-UHFFFAOYSA-N

InChI:

InChI=1S/C9H11N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h4,12H,2H2,1H3,(H4,10,11,13,14,17)

CAS number:

89687-39-8

IUPAC Name:

1-(2-amino-4-oxo-3,4,5,6,7,8-hexahydropteridin-6-yl)propane-1,2-dione

Traditional IUPAC Name:

1-(2-amino-4-oxo-5,6,7,8-tetrahydro-3H-pteridin-6-yl)propane-1,2-dione

SMILES:

CC(=O)C(=O)C1CNC2=C(N1)C(=O)NC(N)=N2

Chemical Taxonomy

Taxonomy Description

This compound belongs to the class of organic compounds known as pterins and derivatives. These are polycyclic aromatic compounds containing a pterin moiety, which consist of a pteridine ring bearing a ketone and an amine group to form 2-aminopteridin-4(3H)-one.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pteridines and derivatives

Sub Class

Pterins and derivatives

Direct Parent

Pterins and derivatives

Alternative Parents

Substituents

Pterin
Secondary aliphatic/aromatic amine
Pyrimidone
Imidolactam
Pyrimidine
Primary aromatic amine
Gamma-aminoketone
Beta-aminoketone
Alpha-diketone
Heteroaromatic compound
Vinylogous amide
Alpha-aminoketone
Lactam
Ketone
Azacycle
Secondary amine
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

a small molecule (6-PYRUVOYL-5678-TETRAHYDROPTERIN )

Physical Properties

State:

Solid

Charge:

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	0.647 mg/mL	ALOGPS
logP	-1	ALOGPS
logP	-1.2	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	11.12	ChemAxon
pKa (Strongest Basic)	4.63	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	125.68 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	67.02 m³·mol^-1	ChemAxon
Polarizability	21.98 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	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:

Dihydroneopterin triphosphate <> Dyspropterin + Triphosphate

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	splash10-0079-0090000000-e366b52537ab82676ed2	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01bi-1960000000-67fc5a413844945d775c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-1091-5920000000-f119b9c54a82b7839351	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0290000000-be2ef388ef865810e924	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000f-1920000000-eb2749d8b0464ac6c26e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0f6x-9300000000-27dfb045e7865625ad19	View in MoNA

References

References:

Bonafe L, Thony B, Leimbacher W, Kierat L, Blau N: Diagnosis of dopa-responsive dystonia and other tetrahydrobiopterin disorders by the study of biopterin metabolism in fibroblasts. Clin Chem. 2001 Mar;47(3):477-85. Pubmed: 11238300
Dhondt JL, Hayte JM: [Screening of tetrahydrobiopterin deficiency among hyperphenylalaninemic patients] Ann Biol Clin (Paris). 2002 Mar-Apr;60(2):165-71. Pubmed: 11937441
Iwanaga N, Yamamasu S, Tachibana D, Nishio J, Nakai Y, Shintaku H, Ishiko O: Activity of synthetic enzymes of tetrahydrobiopterin in the human placenta. Int J Mol Med. 2004 Jan;13(1):117-20. Pubmed: 14654981
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
Niederwieser A, Curtius HC: Tetrahydrobiopterin biosynthetic pathway and deficiency. Enzyme. 1987;38(1-4):302-11. Pubmed: 3326735

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	17804
HMDB ID	HMDB01195
Pubchem Compound ID	128973
Kegg ID	C03684
ChemSpider ID	114280
Wikipedia ID	Dyspropterin
BioCyc ID	6-PYRUVOYL-5678-TETRAHYDROPTERIN
EcoCyc ID	6-PYRUVOYL-5678-TETRAHYDROPTERIN

Dyspropterin (PAMDB000292)

Structure for Dyspropterin (PAMDB000292)