CHEBI:59560 - sapropterin

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name sapropterin
ChEBI ID CHEBI:59560
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
Supplier Information No supplier information found for this compound.
Download Molfile XML SDF
more structures >>
Wikipedia License
Waiting for wikipedia content
Read full article at Wikipedia
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
InChIKey FNKQXYHWGSIFBK-RPDRRWSUSA-N
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 )
cofactor
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).
coenzyme
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.
nutraceutical
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)
IUPAC Name
(6R)-2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-5,6,7,8-tetrahydropteridin-4(3H)-one
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-BH4 ChEBI
6R-L-5,6,7,8-tetrahydrobiopterin ChemIDplus
R-THBP ChEBI
tetrahydrobiopterin DrugBank
Manual Xrefs Databases
2612 DrugCentral
C00018229 KNApSAcK
C00272 KEGG COMPOUND
CPD-14053 MetaCyc
D08505 KEGG DRUG
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 Reaxys Registry Number Reaxys
Citations
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.