Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-23 23:17:02 UTC
Update Date2024-04-30 20:33:05 UTC
Metabolite IDMMDBc0047939
Metabolite Identification
Common Name4a-Hydroxytetrahydrobiopterin
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
Synonyms
ValueSource
(4AS,6R)-4a-hydroxy-L-erythro-5,6,7,8-tetrahydrobiopterinChEBI
(6R)-6-(L-Erythro-1,2-dihydroxypropyl)-5,6,7,8-tetrahydro-4a-hydroxypterinChEBI
4a-Hydroxy-5,6,4,8-tetrahydrobiopterinKegg
6-[(1R,2S)-1,2-Dihydroxypropyl]-5,6,7,8-tetrahydro-4a-hydroxypterinKegg
4a-HTHBHMDB
4a-Hydroxy-5,6,7,8-tetrahydrobiopterinHMDB
4a-Hydroxy-L-erythro-5,6,7,8-tetrahydrobiopterinHMDB
4a-HydroxytetrahydrobiopterinHMDB
Molecular FormulaC9H15N5O4
Average Mass257.25
Monoisotopic Mass257.112403983
IUPAC Name(4aS,6R)-2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-4a-hydroxy-4,4a,5,6,7,8-hexahydropteridin-4-one
Traditional Name(4aS,6R)-2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-4a-hydroxy-5,6,7,8-tetrahydropteridin-4-one
CAS Registry Number1379003-93-6
SMILES
[H][C@@]1(CNC2=NC(N)=NC(=O)[C@]2(O)N1)[C@@H](O)[C@H](C)O
InChI Identifier
InChI=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