Record Information |
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Version | 4.0 |
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Status | Expected but not Quantified |
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Creation Date | 2006-05-22 14:17:45 UTC |
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Update Date | 2020-04-22 18:02:13 UTC |
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HMDB ID | HMDB0002275 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 7,8-Dihydroneopterin |
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Description | 7,8-Dihydroneopterin, also known as dihydroneopterin, 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 synthesized in several parts of the body, including the pineal gland. 7,8-Dihydroneopterin is a strong basic compound (based on its pKa). Within humans, 7,8-dihydroneopterin participates in a number of enzymatic reactions. In particular, 7,8-dihydroneopterin can be biosynthesized from sepiapterin; which is catalyzed by the enzyme sepiapterin reductase or carbonyl reductase [NADPH] 1. In humans, 7,8-dihydroneopterin is involved in the metabolic disorder called hyperphenylalaninemia due to 6-pyruvoyltetrahydropterin synthase (PTPS) deficiency. 7,8-Dihydroneopterin is produced by human monocyte-derived macrophages upon stimulation with interferon-gamma. Increased amounts of 7,8-dihydroneopterin in human body fluids are found in many disorders, including viral infections and autoimmune diseases (PMID: 12804528 ). |
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Structure | |
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Synonyms | Value | Source |
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2-amino-7,8-dihydro-6-(1,2,3-TRIHYDROXYPROPYL)-4(1H)-pteridinone | ChEBI | Dihydroneopterin | ChEBI | 2-Amino-4-hydroxy-6-(D-erythro-1,2,3-trihydroxypropyl)-7,8-dihydropteridine | ChEBI | 7,8-Dihydro-neopterin | MeSH | 2-Amino-4-hydroxy-6-(D-erythro-1',2',3'-trihydroxypropyl)-7,8-dihydropteridine | HMDB | 2-Amino-4-hydroxy-6-(D-erythro-1’,2’,3’-trihydroxypropyl)-7,8-dihydropteridine | HMDB | 2-Amino-7,8-dihydro-6-[(1S,2R)-1,2,3-trihydroxypropyl]-4(3H)-pteridinone | HMDB | 7,8-Dihydro-D-erythro-neopterin | HMDB | 7,8-Dihydro-D-neopterin | HMDB | 7,8-Dihydroneopterin | HMDB | D-erythro-7,8-Dihydroneopterin | HMDB |
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Chemical Formula | C9H13N5O4 |
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Average Molecular Weight | 255.2306 |
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Monoisotopic Molecular Weight | 255.096753929 |
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IUPAC Name | 2-amino-6-[(1S,2R)-1,2,3-trihydroxypropyl]-1,4,7,8-tetrahydropteridin-4-one |
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Traditional Name | 2-amino-6-[(1S,2R)-1,2,3-trihydroxypropyl]-7,8-dihydro-1H-pteridin-4-one |
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CAS Registry Number | 1218-98-0 |
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SMILES | NC1=NC(=O)C2=C(NCC(=N2)[C@H](O)[C@H](O)CO)N1 |
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InChI Identifier | 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)/t4-,6+/m1/s1 |
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InChI Key | YQIFAMYNGGOTFB-XINAWCOVSA-N |
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Chemical Taxonomy |
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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. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Pteridines and derivatives |
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Sub Class | Pterins and derivatives |
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Direct Parent | Biopterins and derivatives |
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Alternative Parents | |
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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
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Ontology |
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Disposition | Source: |
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Process | Naturally occurring process: |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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General References | - 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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, 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
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