You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information |
---|
Version | 4.0 |
---|
Status | Detected and Quantified |
---|
Creation Date | 2005-11-16 15:48:42 UTC |
---|
Update Date | 2020-10-09 20:57:10 UTC |
---|
HMDB ID | HMDB0000038 |
---|
Secondary Accession Numbers | |
---|
Metabolite Identification |
---|
Common Name | Dihydrobiopterin |
---|
Description | Dihydrobiopterin, also known as BH2, 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. Dihydrobiopterin is an extremely weak basic (essentially neutral) compound (based on its pKa). Dihydrobiopterin exists in all eukaryotes, ranging from yeast to humans. Dihydrobiopterin can be biosynthesized from tetrahydrobiopterin through its interaction with the enzyme dihydropteridine reductase. In humans, dihydrobiopterin is involved in the metabolic disorder hyperphenylalaninemia due to dihydropteridine reductase (DHPR) deficiency. |
---|
Structure | |
---|
Synonyms | Value | Source |
---|
7,8-DIHYDROBIOPTERIN | ChEBI | Dihydrobiopterin | ChEBI | L-Erythro-Q-dihydrobiopterin | ChEBI | Q-BH2 | ChEBI | Quinonoid dihydrobiopterin | ChEBI | L-erythro-Dihydrobiopterin | MeSH | 7,8-Dihydro-L-biopterin | HMDB | L-erythro-7,8-Dihydrobiopterin | HMDB | BH2 | HMDB |
|
---|
Chemical Formula | C9H13N5O3 |
---|
Average Molecular Weight | 239.2312 |
---|
Monoisotopic Molecular Weight | 239.101839307 |
---|
IUPAC Name | 2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-1,4,7,8-tetrahydropteridin-4-one |
---|
Traditional Name | dihydrobiopterin |
---|
CAS Registry Number | 6779-87-9 |
---|
SMILES | C[C@H](O)[C@H](O)C1=NC2=C(NC1)NC(N)=NC2=O |
---|
InChI Identifier | InChI=1S/C9H13N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h3,6,15-16H,2H2,1H3,(H4,10,11,13,14,17)/t3-,6-/m0/s1 |
---|
InChI Key | FEMXZDUTFRTWPE-DZSWIPIPSA-N |
---|
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 | |
---|
Substituents | - Biopterin
- Secondary aliphatic/aromatic amine
- Hydroxypyrimidine
- Pyrimidine
- Heteroaromatic compound
- 1,2-diol
- Ketimine
- Secondary alcohol
- Azacycle
- Organic 1,3-dipolar compound
- Propargyl-type 1,3-dipolar organic compound
- Secondary amine
- Hydrocarbon derivative
- Organic oxygen compound
- Organooxygen compound
- Organonitrogen compound
- Organopnictogen compound
- Imine
- Organic nitrogen compound
- Amine
- Alcohol
- Aromatic heteropolycyclic compound
|
---|
Molecular Framework | Aromatic heteropolycyclic compounds |
---|
External Descriptors | |
---|
Ontology |
---|
|
Physiological effect | Health effect: |
---|
Disposition | Source: Biological location: |
---|
Process | Naturally occurring process: |
---|
Physical Properties |
---|
State | Solid |
---|
Experimental Properties | Property | Value | Reference |
---|
Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
|
---|
Predicted Properties | |
---|
Spectra |
---|
| Spectrum Type | Description | Splash Key | View |
---|
Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-01ox-8930000000-836b0568b603906f549d | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-000i-0190000000-b23b7cc50e3b7bda01be | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-0092-3900000000-a352eac2af4690fb47f1 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-014i-9400000000-054ffe617ee964dda203 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-006x-0190000000-d7c2e475a8d3f7b4994f | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-022c-0890000000-00cee7b9f9a6dd10e984 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-03k9-1900000000-0095b515a0b62e12a2a2 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-0390000000-4091667943de90fcbcad | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0006-1930000000-034022c1ca4ad39363fd | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9400000000-4251e4ef4f844b6962ad | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | Spectrum |
|
---|
Biological Properties |
---|
Cellular Locations | |
---|
Biospecimen Locations | - Blood
- Cerebrospinal Fluid (CSF)
- Feces
- Saliva
|
---|
Tissue Locations | Not Available |
---|
Pathways | |
---|
Normal Concentrations |
---|
| |
Blood | Detected and Quantified | 0.006 +/- 0.0003 uM | Adult (>18 years old) | Both | Normal | | details | Cerebrospinal Fluid (CSF) | Detected and Quantified | 0.0004-0.014 uM | Adult (>18 years old) | Both | Normal | | details | Saliva | Detected and Quantified | 8.25 +/- 8.34 uM | Adult (>18 years old) | Female | Normal | | details | Saliva | Detected and Quantified | 1.22 +/- 3.60 uM | Adult (>18 years old) | Not Specified | Normal | | details | Saliva | Detected and Quantified | 10.8 +/- 14.7 uM | Adult (>18 years old) | Not Specified | Normal | | details | Saliva | Detected and Quantified | 23.6 +/- 28.7 uM | Adult (>18 years old) | Both | Normal | | details |
|
---|
Abnormal Concentrations |
---|
| |
Blood | Detected and Quantified | 0.0635 +/- 0.0041 uM | Adult (>18 years old) | Both | Kidney disease | | details | Feces | Detected but not Quantified | Not Quantified | Children (1-13 years old) | Both | Enthesitis-related arthritis | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Colorectal Cancer | | details |
|
---|
Associated Disorders and Diseases |
---|
Disease References | Kidney disease |
---|
- Yokoyama K, Tajima M, Yoshida H, Nakayama M, Tokutome G, Sakagami H, Hosoya T: Plasma pteridine concentrations in patients with chronic renal failure. Nephrol Dial Transplant. 2002 Jun;17(6):1032-6. [PubMed:12032193 ]
| Colorectal cancer |
---|
- Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
|
|
---|
Associated OMIM IDs | |
---|
External Links |
---|
DrugBank ID | DB04400 |
---|
Phenol Explorer Compound ID | Not Available |
---|
FooDB ID | FDB021884 |
---|
KNApSAcK ID | Not Available |
---|
Chemspider ID | 106382 |
---|
KEGG Compound ID | C02953 |
---|
BioCyc ID | CPD-15159 |
---|
BiGG ID | Not Available |
---|
Wikipedia Link | Dihydrobiopterin |
---|
METLIN ID | Not Available |
---|
PubChem Compound | 119055 |
---|
PDB ID | Not Available |
---|
ChEBI ID | 43029 |
---|
Food Biomarker Ontology | Not Available |
---|
VMH ID | Not Available |
---|
MarkerDB ID | MDB00000019 |
---|
References |
---|
Synthesis Reference | Gal E M. Synthesis and quantitative aspects of dihydrobiopterin control of cerebral serotonin levels. Advances in experimental medicine and biology (1981), 133 197-206. |
---|
Material Safety Data Sheet (MSDS) | Download (PDF) |
---|
General References | - Witteveen CF, Giovanelli J, Kaufman S: Reduction of quinonoid dihydrobiopterin to tetrahydrobiopterin by nitric oxide synthase. J Biol Chem. 1996 Feb 23;271(8):4143-7. [PubMed:8626754 ]
- Niederwieser A, Curtius HC, Bettoni O, Bieri J, Schircks B, Viscontini M, Schaub J: Atypical phenylketonuria caused by 7, 8-dihydrobiopterin synthetase deficiency. Lancet. 1979 Jan 20;1(8108):131-3. [PubMed:84153 ]
- Topal G, Brunet A, Millanvoye E, Boucher JL, Rendu F, Devynck MA, David-Dufilho M: Homocysteine induces oxidative stress by uncoupling of NO synthase activity through reduction of tetrahydrobiopterin. Free Radic Biol Med. 2004 Jun 15;36(12):1532-41. [PubMed:15182855 ]
- Yokoyama K, Tajima M, Yoshida H, Nakayama M, Tokutome G, Sakagami H, Hosoya T: Plasma pteridine concentrations in patients with chronic renal failure. Nephrol Dial Transplant. 2002 Jun;17(6):1032-6. [PubMed:12032193 ]
- Hagedoorn PL, Schmidt PP, Andersson KK, Hagen WR, Flatmark T, Martinez A: The effect of substrate, dihydrobiopterin, and dopamine on the EPR spectroscopic properties and the midpoint potential of the catalytic iron in recombinant human phenylalanine hydroxylase. J Biol Chem. 2001 Jun 22;276(25):22850-6. Epub 2001 Apr 11. [PubMed:11301319 ]
- Leeming RJ, Blair JA, Melikian V, O'Gorman DJ: Biopterin derivatives in human body fluids and tissues. J Clin Pathol. 1976 May;29(5):444-51. [PubMed:932231 ]
- Howells DW, Hyland K: Direct analysis of tetrahydrobiopterin in cerebrospinal fluid by high-performance liquid chromatography with redox electrochemistry: prevention of autoxidation during storage and analysis. Clin Chim Acta. 1987 Jul 30;167(1):23-30. [PubMed:3665086 ]
- Goodwill KE, Sabatier C, Stevens RC: Crystal structure of tyrosine hydroxylase with bound cofactor analogue and iron at 2.3 A resolution: self-hydroxylation of Phe300 and the pterin-binding site. Biochemistry. 1998 Sep 29;37(39):13437-45. [PubMed:9753429 ]
- Bonafe L, Thony B, Penzien JM, Czarnecki B, Blau N: Mutations in the sepiapterin reductase gene cause a novel tetrahydrobiopterin-dependent monoamine-neurotransmitter deficiency without hyperphenylalaninemia. Am J Hum Genet. 2001 Aug;69(2):269-77. Epub 2001 Jul 6. [PubMed:11443547 ]
- Shinozaki K, Hirayama A, Nishio Y, Yoshida Y, Ohtani T, Okamura T, Masada M, Kikkawa R, Kodama K, Kashiwagi A: Coronary endothelial dysfunction in the insulin-resistant state is linked to abnormal pteridine metabolism and vascular oxidative stress. J Am Coll Cardiol. 2001 Dec;38(7):1821-8. [PubMed:11738280 ]
|
---|