sapropterin

Ligand id: 5276

Name: sapropterin

Structure and Physico-chemical Properties

2D Structure
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Calculated Physico-chemical Properties
Hydrogen bond acceptors 7
Hydrogen bond donors 6
Rotatable bonds 2
Topological polar surface area 136.29
Molecular weight 241.12
XLogP -0.1
No. Lipinski's rules broken 1

Molecular properties generated using the CDK

Classification
Compound class Metabolite or derivative
Approved drug? Yes (FDA (2007), EMA (2008))
IUPAC Name
(6R)-2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-3,4,5,6,7,8-hexahydropteridin-4-one
International Nonproprietary Names
INN number INN
6553 sapropterin
Synonyms
Kuvan® | sapropterin dihydrochloride | SUN-0588 | T-1401 | tetrahydrobiopterin (THB)
Comments
Sapropterin (also known as tetrahydrobiopterin or BH4) is an essential enzymatic cofactor for aromatic amino acid hydroxylase enzymes; phenylalanine hydroxylase (PAH), tryptophan hydroxylase, tyrosine hydroxylase and for nitric oxide synthase. It is used by PAH to degrade phenylalanine, and is required for the biosynthesis of the neurotransmitters serotonin, melatonin, dopamine, norepinephrine (noradrenaline) and epinephrine (adrenaline).
Sapropterin is produced via a pathway of reactions catalysed by the enzymes GTP cyclohydrolase I (GCH1; the primary and rate-limiting reaction), 6-pyruvoyltetrahydropterin synthase (PTPS) and sepiapterin reductase (SR; the terminal reaction).
Database Links
CAS Registry No. 17528-72-2
ChEBI CHEBI:59560
ChEMBL Ligand CHEMBL1201774
DrugBank Ligand DB00360
GtoPdb PubChem SID 178101959
PubChem CID 44257
RCSB PDB Ligand H4B
Search Google for chemical match using the InChIKey FNKQXYHWGSIFBK-RPDRRWSUSA-N
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Search PubMed clinical trials sapropterin
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Search UniChem for chemical match using the InChIKey FNKQXYHWGSIFBK-RPDRRWSUSA-N
Search UniChem for chemicals with the same backbone FNKQXYHWGSIFBK
SynPHARM 79537 (in complex with L-Phenylalanine hydroxylase )
Wikipedia Tetrahydrobiopterin