| Record Information |
| Version |
3.5 |
| Creation Date |
2005-11-16 08:48:42 -0700 |
| Update Date |
2013-02-08 17:07:48 -0700 |
| HMDB ID |
HMDB00038 |
| Secondary Accession Numbers |
None |
| Metabolite Identification |
| Common Name |
Dihydrobiopterin |
| Description |
Dihydrobiopterin (BH2) is an oxidation product of tetrahydrobiopterin. Tetrahydrobiopterin is a natural occurring cofactor of the aromatic amino acid hydroxylase and is involved in the synthesis of tyrosine and the neurotransmitters dopamine and serotonin. Tetrahydrobiopterin is also essential for nitric oxide synthase catalyzed oxidation of L-arginine to L-citrulline and nitric oxide. |
| Structure |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
|
| Synonyms |
- (6R)-6-(L-erythro-1,2-Dihydroxypropyl)-7,8-dihydro-6H-pterin
- (S-(R*,S*))-2-amino-6-(1,2-dihydroxypropyl)-7,8-dihydro-4(1H)-Pteridinone
- 2-Amino-6-((1R,2S)-1,2-dihydroxypropyl)-7,8-dihydro-4(1H)-Pteridinone
- 2-Amino-6-(1,2-dihydroxypropyl)-7,8-dihydro-4(1H)-Pteridinone
- 6,7-Dihydrobiopterin
- 7,8-Dihydro-L-biopterin
- 7,8-Dihydrobiopterin
- BH2
- Dihydrobiopterin
- L-Erythro-1-(2-amino-7,8-dihydro-4-hydroxy-6-pteridinyl)-1,2-Propanediol
- L-Erythro-7,8-Dihydrobiopterin
- L-Erythro-Dihydrobiopterin
- L-Erythro-q-Dihydrobiopterin
- Quinoid-dihydrobiopterin
- Quinonoid dihydrobiopterin
|
| Chemical Formula |
C9H13N5O3 |
| Average Molecular Weight |
239.2312 |
| Monoisotopic Molecular Weight |
239.101839307 |
| IUPAC Name |
2-amino-6-(1,2-dihydroxypropyl)-3,4,7,8-tetrahydropteridin-4-one |
| Traditional IUPAC Name |
2-amino-6-(1,2-dihydroxypropyl)-7,8-dihydro-3H-pteridin-4-one |
| CAS Registry Number |
6779-87-9 |
| SMILES |
CC(O)C(O)C1=NC2=C(NC1)N=C(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) |
| InChI Key |
FEMXZDUTFRTWPE-UHFFFAOYSA-N |
| Chemical Taxonomy |
| Kingdom |
Organic Compounds |
| Super Class |
Aromatic Heteropolycyclic Compounds |
| Class |
Pteridines and Derivatives |
| Sub Class |
Pterins and Derivatives |
| Other Descriptors |
- Pterins and Derivatives
- a biopterin(Cyc)
|
| Substituents |
- 1,2 Diol
- 1,3 Aminoalcohol
- Aminopyrimidine
- Imine
- Pyrimidine
- Pyrimidone
- Secondary Alcohol
|
| Direct Parent |
Biopterins and Derivatives |
| Ontology |
| Status |
Detected and Quantified |
| Origin |
|
| Biofunction |
- Component of Folate biosynthesis
|
| Application |
Not Available |
| Cellular locations |
|
| 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 |
|
|
| Biological Properties |
| Cellular Locations |
|
| Biofluid Locations |
- Blood
- Cerebrospinal Fluid (CSF)
|
| Tissue Location |
Not Available
|
| Pathways |
|
| Normal Concentrations |
|
| Blood |
Detected and Quantified |
|
0.006 +/- 0.0003 uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.0004-0.014 uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
|
| Abnormal Concentrations |
|
| Blood |
Detected and Quantified |
|
0.0635 +/- 0.0041 uM |
Adult (>18 years old) |
Both |
Kidney disease |
Chronic renal failure, undergoing hemodialysis,...
|
|
| 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
|
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| Associated OMIM IDs |
None |
| External Links |
| DrugBank ID |
Not Available |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB021884 |
| KNApSAcK ID |
Not Available |
| Chemspider ID |
247  |
| KEGG Compound ID |
C02953  |
| BioCyc ID |
BIOPTERIN  |
| BiGG ID |
Not Available |
| Wikipedia Link |
Dihydrobiopterin  |
| NuGOwiki Link |
HMDB00038  |
| Metagene Link |
HMDB00038  |
| METLIN ID |
5106  |
| PubChem Compound |
252  |
| PDB ID |
1DCP  |
| ChEBI ID |
64277  |
| 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
|
| Enzymes |
| Name: |
Tyrosinase
|
| Reactions: |
- L-tyrosine + L-dopa + O2 = L-dopa + dopaquinone + H2O [RN:R02078]
|
| Gene Name: |
TYR |
| Uniprot ID: |
P14679  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
|
| Name: |
Tyrosine 3-monooxygenase
|
| Reactions: |
- L-tyrosine + tetrahydrobiopterin + O2 = 3,4-dihydroxy-L-phenylalanine + 4a-hydroxytetrahydrobiopterin [RN:R07212]
|
| Gene Name: |
TH |
| Uniprot ID: |
P07101  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
|
| Name: |
Sepiapterin reductase
|
| Reactions: |
- (1) 7,8-dihydrobiopterin + NADP+ = sepiapterin + NADPH + H+ [RN:R02975]
- (2) tetrahydrobiopterin + 2 NADP+ = 6-pyruvoyl-5,6,7,8-tetrahydropterin + 2 NADPH + 2 H+ [RN:R08208]
|
| Gene Name: |
SPR |
| Uniprot ID: |
P35270  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
|
| Name: |
Tryptophan 5-hydroxylase 1
|
| Reactions: |
- L-tryptophan + tetrahydrobiopterin + O2 = 5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin [RN:R07213]
|
| Gene Name: |
TPH1 |
| Uniprot ID: |
P17752  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
|
| Name: |
Dihydropteridine reductase
|
| Reactions: |
- a 5,6,7,8-tetrahydropteridine + NAD(P)+ = a 6,7-dihydropteridine + NAD(P)H + H+ [RN:R07354 R07355]
|
| Gene Name: |
QDPR |
| Uniprot ID: |
P09417  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
|
| Name: |
Dihydrofolate reductase
|
| Reactions: |
- 5,6,7,8-tetrahydrofolate + NADP+ = 7,8-dihydrofolate + NADPH + H+ [RN:R00939]
|
| Gene Name: |
DHFR |
| Uniprot ID: |
P00374  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
|
|
|
|
|
| Name: |
Pterin-4-alpha-carbinolamine dehydratase
|
| Reactions: |
- (6R)-6-(L-erythro-1,2-dihydroxypropyl)-5,6,7,8-tetrahydro-4a- hydroxypterin = (6R)-6-(L-erythro-1,2-dihydroxypropyl)-7,8-dihydro-6H-pterin + H2O [RN:R04734]
|
| Gene Name: |
PCBD1 |
| Uniprot ID: |
P61457  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
|