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Dihydrobiopterin (YMDB00030)

Identification
YMDB IDYMDB00030
NameDihydrobiopterin
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionDihydrobiopterin, 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.
Structure
Thumb
MOLSDFPDBSMILESInChI
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
  • Q-BH2
  • Quinoid-dihydrobiopterin
  • Quinonoid dihydro-(6H)-biopterin
  • Quinonoid dihydrobiopterin
CAS number6779-87-9
WeightAverage: 239.2312
Monoisotopic: 239.101839307
InChI KeyFEMXZDUTFRTWPE-UHFFFAOYSA-N
InChIInChI=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)
IUPAC Name2-amino-6-(1,2-dihydroxypropyl)-3,4,7,8-tetrahydropteridin-4-one
Traditional IUPAC Name7,8-dihydrobiopterin
Chemical FormulaC9H13N5O3
SMILES[H]OC([H])(C1=NC2=C(N=C(N([H])[H])N([H])C2=O)N([H])C1([H])[H])C([H])(O[H])C([H])([H])[H]
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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPteridines and derivatives
Sub ClassPterins and derivatives
Direct ParentBiopterins 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 FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility1.63 g/LALOGPS
logP-1.6ALOGPS
logP-1.9ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)7.62ChemAxon
pKa (Strongest Basic)0.59ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area132.33 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity68.31 m³·mol⁻¹ChemAxon
Polarizability23.04 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01ox-8930000000-836b0568b603906f549dJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0103-9108000000-2cc35139ca2f2f86d361JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-0190000000-b23b7cc50e3b7bda01beJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0092-3900000000-a352eac2af4690fb47f1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014i-9400000000-054ffe617ee964dda203JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0390000000-4091667943de90fcbcadJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-1930000000-034022c1ca4ad39363fdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9400000000-4251e4ef4f844b6962adJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006x-0190000000-d7c2e475a8d3f7b4994fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-022c-0890000000-00cee7b9f9a6dd10e984JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03k9-1900000000-0095b515a0b62e12a2a2JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
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.
External Links:
ResourceLink
CHEBI ID15375
HMDB IDHMDB00038
Pubchem Compound ID252
Kegg IDC02953
ChemSpider ID247
FOODB IDFDB021884
WikipediaDihydrobiopterin
BioCyc IDBIOPTERIN

Enzymes

Protein Details
1. Putative pterin-4-alpha-carbinolamine dehydratase
General function:
Involved in 4-alpha-hydroxytetrahydrobiopterin dehydratase activity
Specific function:
(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 + H(2)O
Gene Name:
Not Available
Uniprot ID:
P38744
Molecular weight:
14026.0
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 + H(2)O.