Showing Metabocard for (4aS,6R)-4a-hydroxy-L-erythro-5,6,7,8-tetrahydrobiopterin (BASm0000388)

Common Name(4as,6r)-4a-hydroxy-l-erythro-5,6,7,8-tetrahydrobiopterin
DescriptionTetrahydrobiopterin (BH4) is essential for catalyzing the conversion of phenylalanine into tyrosine by phenylalanine hydroxylase. During this physiological reaction, the oxidation of BH4 creates 4a-hydroxytetrahydropterin (CAS: 70110-58-6) intermediates and hydrogen peroxide is formed. The hydrogen peroxide and the hydroxytetrahydropterin can both be derived from alternate breakdown routes of a common precursor, the corresponding 4a-hydroperoxytetrahydropterin (PMID: 8323303 ).
Structure
Molecular FormulaC9H15N5O4
Average Mass257.25000
Monoisotopic Mass257.11240
IUPAC Name2-amino-6-(1,2-dihydroxypropyl)-4a-hydroxy-4,4a,5,6,7,8-hexahydropteridin-4-one
Traditional Name2-amino-6-(1,2-dihydroxypropyl)-4a-hydroxy-5,6,7,8-tetrahydropteridin-4-one
CAS Registry Number1379003-93-6
SMILESC[C@H](O)[C@H](O)[C@H]1CNC2=NC(N)=NC(=O)[C@]2(O)N1
InChI IdentifierInChI=1S/C9H15N5O4/c1-3(15)5(16)4-2-11-6-9(18,14-4)7(17)13-8(10)12-6/h3-5,14-16,18H,2H2,1H3,(H3,10,11,12,13,17)/t3-,4+,5-,9-/m0/s1
InChI KeyKJKIEFUPAPPGBC-XXKOCQOQSA-N
CHEBI IDCHEBI:15642
HMDB IDHMDB0002281
Pathways
NameSMPDB/PathBank
Tyrosine metabolism
Tryptophan metabolism
Phenylalanine and Tyrosine Metabolism
Alkaptonuria
Hawkinsinuria
Phenylketonuria
Tyrosinemia Type I
Tyrosinemia Type 2 (or Richner-Hanhart syndrome)
Tyrosinemia Type 3 (TYRO3)
Disulfiram Action Pathway
Tyrosinemia, transient, of the newborn
Dopamine beta-hydroxylase deficiency
Monoamine oxidase-a deficiency (MAO-A)
StateSolid
Water Solubility4.81e+00 g/l
logP-2.29
logS-1.73
pKa (Strongest Acidic)9.81
pKa (Strongest Basic)3.85
Hydrogen Acceptor Count9
Hydrogen Donor Count6
Polar Surface Area152.56 Ų
Rotatable Bond Count2
Physiological Charge0
Formal Charge0
Refractivity58.60 m³·mol⁻¹
Polarizability24.20

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