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Human Metabolome Database Version 3.5

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Showing metabocard for Dihydrobiopterin (HMDB00038)

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 Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (6R)-6-(L-erythro-1,2-Dihydroxypropyl)-7,8-dihydro-6H-pterin
  2. (S-(R*,S*))-2-amino-6-(1,2-dihydroxypropyl)-7,8-dihydro-4(1H)-Pteridinone
  3. 2-Amino-6-((1R,2S)-1,2-dihydroxypropyl)-7,8-dihydro-4(1H)-Pteridinone
  4. 2-Amino-6-(1,2-dihydroxypropyl)-7,8-dihydro-4(1H)-Pteridinone
  5. 6,7-Dihydrobiopterin
  6. 7,8-Dihydro-L-biopterin
  7. 7,8-Dihydrobiopterin
  8. BH2
  9. Dihydrobiopterin
  10. L-Erythro-1-(2-amino-7,8-dihydro-4-hydroxy-6-pteridinyl)-1,2-Propanediol
  11. L-Erythro-7,8-Dihydrobiopterin
  12. L-Erythro-Dihydrobiopterin
  13. L-Erythro-q-Dihydrobiopterin
  14. Quinoid-dihydrobiopterin
  15. 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
  • Endogenous
Biofunction
  • Component of Folate biosynthesis
Application Not Available
Cellular locations
  • Cytoplasm
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
Property Value Source
Water Solubility 1.63 g/L ALOGPS
LogP -1.65 ALOGPS
LogP -1.9 ChemAxon
LogS -2.17 ALOGPS
pKa (strongest acidic) 10.81 ChemAxon
pKa (strongest basic) 3.67 ChemAxon
Hydrogen Acceptor Count 7 ChemAxon
Hydrogen Donor Count 5 ChemAxon
Polar Surface Area 132.33 A2 ChemAxon
Rotatable Bond Count 2 ChemAxon
Refractivity 68.31 ChemAxon
Polarizability 23.04 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
Tissue Location Not Available
Pathways
Name SMPDB Link KEGG Link
Pterine Biosynthesis SMP00005 map00790 Link_out
Catecholamine Biosynthesis SMP00012 map00350 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
0.006 +/- 0.0003 uM Adult (>18 years old) Both Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
0.0004-0.014 uM Adult (>18 years old) Both Normal Not Available
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
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 Link_out
    Associated OMIM IDs None
    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 Link_out
    KEGG Compound ID C02953 Link_out
    BioCyc ID BIOPTERIN Link_out
    BiGG ID Not Available
    Wikipedia Link Dihydrobiopterin Link_out
    NuGOwiki Link HMDB00038 Link_out
    Metagene Link HMDB00038 Link_out
    METLIN ID 5106 Link_out
    PubChem Compound 252 Link_out
    PDB ID 1DCP Link_out
    ChEBI ID 64277 Link_out
    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
    1. 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 Link_out
    2. 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 Link_out
    3. 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 Link_out
    4. 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 Link_out
    5. 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 Link_out
    6. 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 Link_out
    7. 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 Link_out
    8. 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 Link_out
    9. 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 Link_out
    10. 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 Link_out
    Enzymes
    Name: Tyrosinase
    Reactions:
    • L-tyrosine + L-dopa + O2 = L-dopa + dopaquinone + H2O [RN:R02078]
    Gene Name: TYR
    Uniprot ID: P14679 Link_out
    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 Link_out
    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 Link_out
    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 Link_out
    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 Link_out
    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 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Nitric oxide synthase, brain
    Reactions:
    • L-arginine + n NADPH + n H+ + m O2 = citrulline + nitric oxide + n NADP+ [RN:R00557]
    Gene Name: NOS1
    Uniprot ID: P29475 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Nitric oxide synthase, endothelial
    Reactions:
    • L-arginine + n NADPH + n H+ + m O2 = citrulline + nitric oxide + n NADP+ [RN:R00557]
    Gene Name: NOS3
    Uniprot ID: P29474 Link_out
    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 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA