P. aeruginosa Metabolome Database: 7,8-Dihydroneopterin (PAMDB000454)

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

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 12:54:54 PM

Metabolite ID

PAMDB000454

Identification

Name:

7,8-Dihydroneopterin

Description:

7,8-dihydroneopterin (H(2)Neo) is an intermediate in folate biosynthesis pathway. It is converted to glycolaldehyde and 2-amino-4-hydroxy-6-hydroxymethyl-7,8-dihydropteridine via bifunctional dihydroneopterin aldolase/dihydroneopterin triphosphate 2'-epimerase (EC:4.1.2.25). it is also a substrate of alkaline phosphatase. (KEGG) Dihydromonapterin is a member of the chemical class known as Biopterins and Derivatives. These are coenzymes containing a 2-amino-pteridine-4-one derivative. Dihydromonapterin is an intermediate in the synthesis of tetrahydromonopterin. Tetrahydromonapterin is the major tetrahydropterin in Pseudomonas aeruginosa, although the biological role of tetrahydromonapterin in Pseudomonas aeruginosa is currently unknown.

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

2-Amino-4-hydroxy-6-(D-erythro)-trihydroxypropyldihydropteridin
2-Amino-4-hydroxy-6-(D-erythro-1',2',3'-trihydroxypropyl)-7,8-dihydropteridine
2-Amino-4-hydroxy-6-(D-erythro-1,2,3-trihydroxypropyl)-7,8-dihydropteridine
2-Amino-6-[(1S,2R)-1,2,3-trihydroxypropyl]-7,8-dihydropteridin-4(1H)-one
2-Amino-6-[(1S,2R)-1,2,3-trihydroxypropyl]-7,8-dihydropteridin-4(3H)-one
2-Amino-7,8-dihydro-6-(1,2,3-trihydroxypropyl)-4(1H)-pteridinone
7,8-Dihydro-D-erythro-neopterin
7,8-Dihydro-D-neopterin
7,8-Dihydroneopterin
D-Erythro-7,8-Dihydroneopterin
DHM
DHN
Dihydro-neo-pterin
Dihydroneopterin
H2-MPt
NPR

Chemical Formula:

C₉H₁₃N₅O₄

Average Molecular Weight:

255.2306

Monoisotopic Molecular Weight:

255.096753929

InChI Key:

YQIFAMYNGGOTFB-UHFFFAOYSA-N

InChI:

InChI=1S/C9H13N5O4/c10-9-13-7-5(8(18)14-9)12-3(1-11-7)6(17)4(16)2-15/h4,6,15-17H,1-2H2,(H4,10,11,13,14,18)

CAS number:

1218-98-0

IUPAC Name:

2-amino-6-(1,2,3-trihydroxypropyl)-1,4,7,8-tetrahydropteridin-4-one

Traditional IUPAC Name:

2-amino-6-(1,2,3-trihydroxypropyl)-7,8-dihydro-1H-pteridin-4-one

SMILES:

NC1=NC(=O)C2=C(NCC(=N2)C(O)C(O)CO)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
Secondary aliphatic/aromatic amine
Pyrimidone
Pyrimidine
Primary aromatic amine
Heteroaromatic compound
Vinylogous amide
Secondary alcohol
Polyol
Ketimine
1,2-diol
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Secondary amine
Hydrocarbon derivative
Primary amine
Primary alcohol
Organooxygen compound
Organonitrogen compound
Imine
Amine
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

a small molecule (DIHYDRO-NEO-PTERIN )

Physical Properties

State:

Solid

Charge:

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	1.86 mg/mL	ALOGPS
logP	-2.1	ALOGPS
logP	-3.3	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	7.97	ChemAxon
pKa (Strongest Basic)	3.22	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	152.56 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	69.66 m³·mol^-1	ChemAxon
Polarizability	23.99 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:

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	splash10-0a4i-0090000000-e5dad4abb411efa4feb6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01p9-1790000000-449cabdd2508eefabccc	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03dj-3900000000-b2abed21008ce5fb01bd	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udl-1390000000-1e1c831e7f68ac77caed	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-4950000000-948e3120b1a4f548982b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9300000000-581b6b2fd47ffbefaa0c	View in MoNA

References

References:

Baier-Bitterlich G, Baier G, Fuchs D, Bock G, Hausen A, Utermann G, Pavelka M, Wachter H: Role of 7,8-dihydroneopterin in T-cell apoptosis and HTLV-1 transcription in vitro. Oncogene. 1996 Nov 21;13(10):2281-5. Pubmed: 8950996
Baier-Bitterlich G, Fuchs D, Wachter H: 7,8-Dihydroneopterin upregulates interferon-gamma promoter in T cells. Immunobiology. 1996;196(4):350-5. Pubmed: 9061375
Baier-Bitterlich G, Fuchs D, Zangerle R, Baeuerle PA, Werner ER, Fresser F, Uberall F, Baier G, Wachter H: trans-Activation of the HIV type 1 promoter by 7,8-dihydroneopterin in vitro. AIDS Res Hum Retroviruses. 1997 Jan 20;13(2):173-8. Pubmed: 9007202
Baird SK, Reid L, Hampton MB, Gieseg SP: OxLDL induced cell death is inhibited by the macrophage synthesised pterin, 7,8-dihydroneopterin, in U937 cells but not THP-1 cells. Biochim Biophys Acta. 2005 Sep 30;1745(3):361-9. Pubmed: 16084608
Duggan S, Rait C, Platt A, Gieseg S: Protein and thiol oxidation in cells exposed to peroxyl radicals is inhibited by the macrophage synthesised pterin 7,8-dihydroneopterin. Biochim Biophys Acta. 2002 Aug 19;1591(1-3):139-145. Pubmed: 12183064
Enzinger C, Wirleitner B, Lutz C, Bock G, Tomaselli B, Baier G, Fuchs D, Baier-Bitterlich G: 7,8-Dihydroneopterin induces apoptosis of Jurkat T-lymphocytes via a Bcl-2-sensitive pathway. Eur J Cell Biol. 2002 Apr;81(4):197-202. Pubmed: 12018387
Fuchs D, Reibnegger G, Werner ER, Wachter H: Increased 7,8-dihydroneopterin and reduced methyl-group metabolism in HIV-1 infection. Lancet. 1990 May 12;335(8698):1167. Pubmed: 1971904
Gieseg SP, Cato S: Inhibition of THP-1 cell-mediated low-density lipoprotein oxidation by the macrophage-synthesised pterin, 7,8-dihydroneopterin. Redox Rep. 2003;8(2):113-5. Pubmed: 12804014
Gieseg SP, Maghzal G, Glubb D: Protection of erythrocytes by the macrophage synthesized antioxidant 7,8 dihydroneopterin. Free Radic Res. 2001 Feb;34(2):123-36. Pubmed: 11264890
Gieseg SP, Reibnegger G, Wachter H, Esterbauer H: 7,8 Dihydroneopterin inhibits low density lipoprotein oxidation in vitro. Evidence that this macrophage secreted pteridine is an anti-oxidant. Free Radic Res. 1995 Aug;23(2):123-36. Pubmed: 7581810
Gieseg SP, Whybrow J, Glubb D, Rait C: Protection of U937 cells from free radical damage by the macrophage synthesized antioxidant 7,8-dihydroneopterin. Free Radic Res. 2001 Sep;35(3):311-8. Pubmed: 11697129
Greilberger J, Oettl K, Cvirn G, Reibnegger G, Jurgens G: Modulation of LDL oxidation by 7,8-dihydroneopterin. Free Radic Res. 2004 Jan;38(1):9-17. Pubmed: 15061649
Herpfer I, Greilberger J, Ledinski G, Widner B, Fuchs D, Jurgens G: Neopterin and 7,8-dihydroneopterin interfere with low density lipoprotein oxidation mediated by peroxynitrite and/or copper. Free Radic Res. 2002 May;36(5):509-20. Pubmed: 12150539
Horejsi R, Jung C, Moller R, Tafeit E, Reibnegger G: Generation of carbon monoxide and iron from hemeproteins in the presence of 7,8-dihydroneopterin. Biochim Biophys Acta. 2002 Jun 6;1571(2):124-30. Pubmed: 12049792
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
Pagel H, Fandrey J, Schobersberger W, Fuchs D, Jelkmann W: Effects of neopterin and 7,8-dihydroneopterin on hypoxia-induced renal erythropoietin production. Eur J Haematol. 1999 May;62(5):341-5. Pubmed: 10359064
Speth C, Stockl G, Fuchs D, Wirleitner B, Widner B, Wurzner R, Mohsenipour I, Lass-Florl C, Dierich MP: Inflammation marker 7,8-dihydroneopterin induces apoptosis of neurons and glial cells: a potential contribution to neurodegenerative processes. Immunobiology. 2000 Nov;202(5):460-76. Pubmed: 11205375
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
Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Wirleitner B, Baier-Bitterlich G, Bock G, Widner B, Fuchs D: 7,8-Dihydroneopterin-induced apoptosis in Jurkat T lymphocytes: a comparison with anti-Fas- and hydrogen peroxide-mediated cell death. Biochem Pharmacol. 1998 Nov 1;56(9):1181-7. Pubmed: 9802329
Wirleitner B, Czaputa R, Oettl K, Bock G, Widner B, Reibnegger G, Baier G, Fuchs D, Baier-Bitterlich G: Induction of apoptosis by 7,8-dihydroneopterin: involvement of radical formation. Immunobiology. 2001 May;203(4):629-41. Pubmed: 11402497
Wirleitner B, Obermoser G, Bock G, Neurauter G, Schennach H, Sepp N, Fuchs D: Induction of apoptosis in human blood T cells by 7,8-dihydroneopterin: the difference between healthy controls and patients with systemic lupus erythematosus. Clin Immunol. 2003 Jun;107(3):152-9. Pubmed: 12804528

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

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Links

External Links:

Resource	Link
CHEBI ID	17001
HMDB ID	HMDB02275
Pubchem Compound ID	659
Kegg ID	C04874
ChemSpider ID	639
Wikipedia ID	Not Available
BioCyc ID	DIHYDRO-NEO-PTERIN
EcoCyc ID	DIHYDRO-NEO-PTERIN

7,8-Dihydroneopterin (PAMDB000454)

Structure for 7,8-Dihydroneopterin (PAMDB000454)