MiMeDB: Showing metabocard for Dihydroneopterin (MMDBc0049934)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-04-29 22:46:35 UTC

Update Date

2023-12-14 16:53:09 UTC

Metabolite ID

MMDBc0049934

Metabolite Identification

Common Name

Dihydroneopterin

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 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Molecular Formula

C₉H₁₃N₅O₄

Average Mass

255.2306

Monoisotopic Mass

255.096753929

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

Not Available

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

InChI Key

YQIFAMYNGGOTFB-XINAWCOVSA-N

Chemical Taxonomy

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Not Available

Spectra

Not Available

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191763	Alkaline phosphatase, placental type	Unknown	P05187	Homo sapiens
MMDBp0191766	Intestinal-type alkaline phosphatase	Unknown	P09923	Homo sapiens
MMDBp0191769	Alkaline phosphatase, tissue-nonspecific isozyme	Unknown	P05186	Homo sapiens
MMDBp0191772	Alkaline phosphatase, placental-like	Unknown	P10696	Homo sapiens
MMDBp0192101	6-pyruvoyl tetrahydrobiopterin synthase	Unknown	Q03393	Homo sapiens
MMDBp0194160	RuvB-like 2	Enzyme	Q9Y230	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0007615	Dihydroneopterin	6-Hydroxymethyl dihydropterin	Not Available	VMH	30371894
MMDBr0007674	Dihydroneopterin triphosphate	Dihydroneopterin	Not Available	VMH	30371894
MMDBr0008476	Dihydroneopterin monophosphate	Dihydroneopterin	Not Available	VMH	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria/Eubacteria	Proteobacteria	158	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human feces; pleural fluid plaque; bal; Human stool	Metabolic reconstruction
Bacteria/Eubacteria	Firmicutes	262	Pig ; Human feces; Human ; Cattle ; Human pleural fluid plaque; Human supragingival plaque; Human saliva; Human subgingival plaque	Metabolic reconstruction
Bacteria	Actinobacteria	9	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human ; Human mucosa; Human supragingival plaque; Human subgingival plaque; Human saliva; Cattle	Metabolic reconstruction
Bacteria/Eubacteria	Actinobacteria	89	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human ; Human mucosa; Human supragingival plaque; Human subgingival plaque; Human saliva; Cattle	Metabolic reconstruction
Bacteria/Eubacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Bacteroidetes	127	Human feces; Human appendix biopsy; Human ; Human stool; Human urine; Human gastric fluid; Human saliva; Human supragingival plaque; Human subgingival plaque	Metabolic reconstruction
Bacteria	Proteobacteria	8	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human feces; pleural fluid plaque; bal; Human stool	Metabolic reconstruction
Bacteria	Firmicutes	20	Pig ; Human feces; Human ; Cattle ; Human pleural fluid plaque; Human supragingival plaque; Human saliva; Human subgingival plaque	Metabolic reconstruction
Bacteria/Eubacteria	Fusobacteria	18	Human feces; Human	Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	4		Metabolic reconstruction
Bacteria/Eubacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Synergistetes	1	Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Spirochaetes	1	Human feces	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Archaea	Euryarchaeota	1		Metabolic reconstruction
Bacteria	Synergistetes	1	Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Chlamydiae	3	Human
Bacteria	nah	1
Archaea/Archaea	Euryarchaeota	3		Metabolic reconstruction

Exposure Sources

Source Type	Activity	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

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. doi: 10.1016/0140-6736(90)91176-b. [PubMed:1971904 ]
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. doi: 10.3109/10715769509064027. [PubMed:7581810 ]
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, 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. doi: 10.1089/aid.1997.13.173. [PubMed:9007202 ]
Baier-Bitterlich G, Fuchs D, Wachter H: 7,8-Dihydroneopterin upregulates interferon-gamma promoter in T cells. Immunobiology. 1996;196(4):350-5. doi: 10.1016/s0171-2985(96)80057-x. [PubMed:9061375 ]
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. doi: 10.1016/s0006-2952(98)00168-3. [PubMed:9802329 ]
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. doi: 10.1111/j.1600-0609.1999.tb01913.x. [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. doi: 10.1016/S0171-2985(00)80104-7. [PubMed:11205375 ]
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. doi: 10.1080/10715760100300121. [PubMed:11264890 ]
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. doi: 10.1016/s0171-2985(01)80012-7. [PubMed:11402497 ]
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. doi: 10.1080/10715760100300841. [PubMed:11697129 ]
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. doi: 10.1078/0171-9335-00236. [PubMed:12018387 ]
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. doi: 10.1016/s0304-4165(02)00206-4. [PubMed:12049792 ]
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. doi: 10.1080/10715760290025898. [PubMed:12150539 ]
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. doi: 10.1016/s0167-4889(02)00272-0. [PubMed:12183064 ]
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. doi: 10.1179/135100003125001396. [PubMed:12804014 ]
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. doi: 10.1016/s1521-6616(03)00040-8. [PubMed:12804528 ]
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. doi: 10.1080/10715760310001623322. [PubMed:15061649 ]
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. doi: 10.1016/j.bbamcr.2005.07.001. [PubMed:16084608 ]

Showing metabocard for Dihydroneopterin (MMDBc0049934)

MOL for #<Metabolite:0x00007f3e34e590b0>

3D MOL for #<Metabolite:0x00007f3e34e590b0>

3D SDF for #<Metabolite:0x00007f3e34e590b0>

3D-SDF for #<Metabolite:0x00007f3e34e590b0>

PDB for #<Metabolite:0x00007f3e34e590b0>

3D PDB for #<Metabolite:0x00007f3e34e590b0>

SMILES for #<Metabolite:0x00007f3e34e590b0>

INCHI for #<Metabolite:0x00007f3e34e590b0>

Structure for #<Metabolite:0x00007f3e34e590b0>

3D Structure for #<Metabolite:0x00007f3e34e590b0>