sapropterin   Click here for help

GtoPdb Ligand ID: 5276

Synonyms: Kuvan® | sapropterin dihydrochloride | SUN-0588 | T-1401 | tetrahydrobiopterin (THB)
Approved drug PDB Ligand Immunopharmacology Ligand
sapropterin is an approved drug (FDA (2007), EMA (2008))
Comment: 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).
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2D Structure
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Physico-chemical Properties
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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
SMILES / InChI / InChIKey
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Canonical SMILES CC(C(C1CNc2c(N1)c(=O)[nH]c(n2)N)O)O
Isomeric SMILES C[C@@H]([C@@H]([C@H]1CNc2c(N1)c(=O)[nH]c(n2)N)O)O
InChI InChI=1S/C9H15N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h3-4,6,12,15-16H,2H2,1H3,(H4,10,11,13,14,17)/t3-,4+,6-/m0/s1
InChI Key FNKQXYHWGSIFBK-RPDRRWSUSA-N
Classification Click here for help
Compound class Metabolite or derivative
Approved drug? Yes (FDA (2007), EMA (2008))
IUPAC Name Click here for help
(6R)-2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-3,4,5,6,7,8-hexahydropteridin-4-one
International Nonproprietary Names Click here for help
INN number INN
6553 sapropterin
Synonyms Click here for help
Kuvan® | sapropterin dihydrochloride | SUN-0588 | T-1401 | tetrahydrobiopterin (THB)
Database Links Click here for help
CAS Registry No. 17528-72-2
ChEBI CHEBI:59560
ChEMBL Ligand CHEMBL1201774
DrugBank Ligand DB00360
DrugCentral Ligand 2612
GtoPdb PubChem SID 178101959
PubChem CID 44257
RCSB PDB Ligand H4B
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SynPHARM 79537 (in complex with L-Phenylalanine hydroxylase )
Wikipedia Tetrahydrobiopterin