CHEBI:59560 - sapropterin

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ChEBI Name sapropterin
Definition A tetrahydropterin that is 2-amino-5,6,7,8-tetrahydropteridin-4(3H)-one in which a hydrogen at position 6 is substituted by a 1,2-dihydroxypropyl group (6R,1'R,2'S-enantiomer).
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Kristian Axelsen
Secondary ChEBI IDs CHEBI:64242
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Formula C9H15N5O3
Net Charge 0
Average Mass 241.24710
Monoisotopic Mass 241.11749
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
SMILES [H][C@@]1(CNc2nc(N)[nH]c(=O)c2N1)[C@@H](O)[C@H](C)O
Roles Classification
Biological Role(s): human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
(via 5,6,7,8-tetrahydrobiopterin )
An organic molecule or ion (usually a metal ion) that is required by an enzyme for its activity. It may be attached either loosely (coenzyme) or tightly (prosthetic group).
A low-molecular-weight, non-protein organic compound participating in enzymatic reactions as dissociable acceptor or donor of chemical groups or electrons.
(via 5,6,7,8-tetrahydrobiopterin )
prosthetic group
A tightly bound, specific nonpolypeptide unit in a protein determining and involved in its biological activity.
(via 5,6,7,8-tetrahydrobiopterin )
Application(s): diagnostic agent
A substance administered to aid diagnosis of a disease.
A product in capsule, tablet or liquid form that provide essential nutrients, such as a vitamin, an essential mineral, a protein, an herb, or similar nutritional substance.
(via 5,6,7,8-tetrahydrobiopterin )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing sapropterin (CHEBI:59560) has role coenzyme (CHEBI:23354)
sapropterin (CHEBI:59560) has role cofactor (CHEBI:23357)
sapropterin (CHEBI:59560) has role diagnostic agent (CHEBI:33295)
sapropterin (CHEBI:59560) has role human metabolite (CHEBI:77746)
sapropterin (CHEBI:59560) is a 5,6,7,8-tetrahydrobiopterin (CHEBI:15372)
Incoming sapropterin dihydrochloride (CHEBI:32120) has part sapropterin (CHEBI:59560)
INNs Sources
sapropterin ChemIDplus
sapropterina ChemIDplus
sapropterinum ChemIDplus
Synonyms Sources
(−)-(6R)-2-amino-6-((1R,2S)-1,2-dihydroxypropyl)-5,6,7,8-tetrahydro-4(3H)-pteridinone ChemIDplus
(6R)-L-erythro-5,6,7,8-tetrahydrobiopterin UniProt
(6R)-L-erythro-tetrahydrobiopterin ChEBI
2-Amino-6-(1,2-dihydroxypropyl)-5,6,7,8-tetrahydoro-4(1H)-pteridinone KEGG COMPOUND
5,6,7,8-Tetrahydrobiopterin KEGG COMPOUND
6R-5,6,7,8-tetrahydrobiopterin ChemIDplus
6R-L-5,6,7,8-tetrahydrobiopterin ChemIDplus
tetrahydrobiopterin DrugBank
Manual Xrefs Databases
2612 DrugCentral
C00018229 KNApSAcK
CPD-14053 MetaCyc
DB00360 DrugBank
EP191335 Patent
H4B PDBeChem
HMDB0000787 HMDB
Sapropterin Wikipedia
US4713454 Patent
View more database links
Registry Numbers Types Sources
17528-72-2 CAS Registry Number KEGG COMPOUND
27070-47-9 CAS Registry Number ChemIDplus
4699705 Beilstein Registry Number Beilstein
4699705 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
10333495 PubMed citation SUBMITTER
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Last Modified
26 July 2019
General Comment
2011-03-17 The active enantiomer of tetrahydrobiopterin, sapropterin is a natural co-factor of the three aromatic amino acid hydroxylase enzymes responsible for the conversion of phenylalanine to tyrosine, tyrosine to L-dopa, and tryptophan to 5-hydroxytryptophan. These conversions are particularly important in the biosynthesis of the neurotransmitters serotonin, melatonin, dopamine, noradrenaline and adrenaline. Sapropterin is also an essential cofactor in the biosynthesis of nitric oxide. It is used as its dihydrochloride for the diagnosis and treatment of variant forms of phenylketonuria (hyperphenylalaninaemia) associated with tetrahydrobiopterin deficiency.