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Record Information
Version	2.0
Creation Date	2012-05-31 13:56:27 -0600
Update Date	2015-09-13 12:56:12 -0600
Secondary Accession Numbers	ECMDB02275
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 E. coli, although the biological role of tetrahydromonapterin in E. coli is currently unknown.
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xa949bb9c> Close
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
Weight:	Average: 255.2306 Monoisotopic: 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
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	Secondary alkylarylamines Pyrimidones Aminopyrimidines and derivatives Vinylogous amides Heteroaromatic compounds Secondary alcohols Ketimines Propargyl-type 1,3-dipolar organic compounds Polyols Azacyclic compounds Primary amines Primary alcohols Organopnictogen compounds Organic oxides Hydrocarbon derivatives
Substituents	Biopterin Aminopyrimidine Pyrimidone Secondary aliphatic/aromatic amine Pyrimidine Vinylogous amide Heteroaromatic compound Ketimine Secondary alcohol Azacycle Organic 1,3-dipolar compound Propargyl-type 1,3-dipolar organic compound Secondary amine Polyol Amine Organopnictogen compound Primary amine Primary alcohol Organic oxide Organooxygen compound Organonitrogen compound Hydrocarbon derivative Imine Organic oxygen compound Organic nitrogen compound Alcohol Aromatic heteropolycyclic compound
Molecular Framework	Aromatic heteropolycyclic compounds
External Descriptors	a small molecule (DIHYDRO-NEO-PTERIN )
Physical Properties
State:	Solid
Charge:	0
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 1.15 g/L ALOGPS logP -1.6 ALOGPS logP -3.3 ChemAxon logS -2.4 ALOGPS pKa (Strongest Acidic) 9.37 ChemAxon pKa (Strongest Basic) 0.28 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 9 ChemAxon Hydrogen Donor Count 6 ChemAxon Polar Surface Area 152.56 Ų ChemAxon Rotatable Bond Count 3 ChemAxon Refractivity 69.66 m³·mol⁻¹ ChemAxon Polarizability 23.99 ų 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:	7,8-Dihydroneopterin + Hydrogen ion + NADPH > NADP + Tetrahydromonapterin 7,8-Dihydroneopterin <> 6-Hydroxymethyl dihydropterin + Glycolaldehyde 7,8-Dihydroneopterin <> 7,8-Dihydroneopterin 7,8-Dihydroneopterin <> 7,8-Dihydroneopterin Dihydroneopterin triphosphate + 3 Water <> 7,8-Dihydroneopterin +3 Phosphate Dihydromonapterin-triphosphate + Water > Hydrogen ion + 7,8-Dihydroneopterin + Phosphate Dihydroneopterin monophosphate + Water > 7,8-Dihydroneopterin + Phosphate 7,8-Dihydroneopterin > Glycolaldehyde + 6-Hydroxymethyl dihydropterin Tetrahydromonapterin + NADP < Hydrogen ion + 7,8-Dihydroneopterin + NADPH 7,8-Dihydroneopterin + 7,8-Dihydroneopterin > Glycolaldehyde + 6-Hydroxymethyl dihydropterin 7 7,8-Dihydroneopterin <>6 6-Hydroxymethyl dihydropterin + Glycolaldehyde Dihydroneopterin triphosphate + 3 Water <>7 7,8-Dihydroneopterin +3 Phosphate 7 7,8-Dihydroneopterin <>6 6-Hydroxymethyl dihydropterin + Glycolaldehyde
SMPDB Pathways:	Folate biosynthesis PW000908 GTP degradation PW001888
KEGG Pathways:	Folate biosynthesis ec00790 Metabolic pathways eco01100
EcoCyc Pathways:	6-hydroxymethyl-dihydropterin diphosphate biosynthesis I PWY-6147 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 splash10-03dr-9220000000-602126fb02cae16969f6 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive splash10-0aw9-3292200000-e6b52358cd355e939ab0 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 (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_4_31) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_4_32) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_4_33) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_4_34) - 70eV, Positive Not Available View in JSpectraViewer LC-MS/MS LC-MS/MS Spectrum - Orbitrap 2V, positive splash10-0a4i-0090000000-c40ef232ef8c10af6b4a View in MoNA LC-MS/MS LC-MS/MS Spectrum - Orbitrap 3V, positive splash10-0a4i-0090000000-40779978322477cf298a View in MoNA LC-MS/MS LC-MS/MS Spectrum - Orbitrap 5V, positive splash10-0a4i-0090000000-e49838b4e8d652d72bdf View in MoNA LC-MS/MS LC-MS/MS Spectrum - Orbitrap 7V, positive splash10-0a4r-0390000000-b43231e2e78443a996d7 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Orbitrap 10V, positive splash10-014i-0920000000-5f6d06fef1bff433cb74 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Orbitrap 12V, positive splash10-014i-0900000000-1f59c6362ecd3bf94b79 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Orbitrap 16V, positive splash10-014i-0900000000-5299b47c47609ee94a30 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Orbitrap 20V, positive splash10-014i-1900000000-f31d91ebf5d2ad43354c View in MoNA LC-MS/MS LC-MS/MS Spectrum - Orbitrap 24V, positive splash10-01ba-3900000000-4d3e2458159bb9f65ce6 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Orbitrap 28V, positive splash10-00xs-6900000000-86a6eac4069432a18ae5 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Orbitrap 33V, positive splash10-00r7-9600000000-971378f9c783f6d800ff View in MoNA LC-MS/MS LC-MS/MS Spectrum - Orbitrap 38V, positive splash10-014l-9200000000-687b58605bb70fc727db View in MoNA LC-MS/MS LC-MS/MS Spectrum - Orbitrap 46V, positive splash10-014i-9000000000-b01418dfcc77acb66b6e View in MoNA LC-MS/MS LC-MS/MS Spectrum - n/a 17V, positive splash10-014i-0900000000-5da76eb2e54c7dcf9422 View in MoNA LC-MS/MS LC-MS/MS Spectrum - n/a 17V, positive splash10-014i-0900000000-df54ce2cbff970a469f4 View in MoNA LC-MS/MS LC-MS/MS Spectrum - n/a 17V, positive splash10-004i-0900000000-d6756ef30d881fb25685 View in MoNA LC-MS/MS LC-MS/MS Spectrum - n/a 17V, positive splash10-001l-0900000000-e8baecab87622e9340c6 View in MoNA LC-MS/MS LC-MS/MS Spectrum - n/a 17V, positive splash10-0w29-0900000000-4952089b8c8b79285dea View in MoNA LC-MS/MS LC-MS/MS Spectrum - n/a 17V, positive splash10-0ab9-0690000000-1f127d1244a709e9919f View in MoNA 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 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:	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)	Download (PDF)
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

Enzymes