Sapropterin (CED0007353)

Record Information
Version1.0
Creation Date2016-05-26 05:22:08 UTC
Update Date2026-05-14 16:36:33 UTC
Accession NumberCHEM034958
Identification
Common NameSapropterin
ClassSmall Molecule
Description
Sapropterin is an organic compound with the formula C9H15N5O3 and an average molecular weight of 241.25 g/mol. Sapropterin belongs to the pterins and derivatives, a subclass of pteridines and derivatives within the organic compounds. This compound is found in healthcare, pharmaceuticals, and veterinary products, specifically within alimentary tract and metabolism products, and is administered via the oral exposure route. Sapropterin acts as a cofactor for four recorded protein targets: Phenylalanine-4-hydroxylase (PAH), Nitric oxide synthase 3 (NOS3), Tyrosine 3-monooxygenase (TH), and Tryptophan 5-hydroxylase 1 (TPH1).
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(-)-(6R)-2-Amino-6-((1R,2S)-1,2-dihydroxypropyl)-5,6,7,8-tetrahydro-4(3H)-pteridinoneChEBI
(6R)-L-Erythro-5,6,7,8-tetrahydrobiopterinChEBI
(6R)-L-Erythro-tetrahydrobiopterinChEBI
2-Amino-6-(1,2-dihydroxypropyl)-5,6,7,8-tetrahydoro-4(1H)-pteridinoneChEBI
5,6,7,8-TetrahydrobiopterinChEBI
6R-5,6,7,8-TetrahydrobiopterinChEBI
6R-BH4ChEBI
6R-L-5,6,7,8-TetrahydrobiopterinChEBI
R-THBPChEBI
SapropterinaChEBI
SapropterinumChEBI
TetrahydrobiopterinChEBI
5,6,7,8-erythro-TetrahydrobiopterinMeSH, HMDB
5,6,7,8-tetrahydro-L-ErythrobiopterinMeSH, HMDB
5,6,7,8-Tetrahydrobiopterin, (S-(r*,s*))-isomerMeSH, HMDB
5,6,7,8-TetrahydrodictyopterinMeSH, HMDB
6R-L-erythro-5,6,7,8-TetrahydrobiopterinMeSH, HMDB
BPH4MeSH, HMDB
D-threo-TetrahydrobiopterinMeSH, HMDB
THBPMeSH, HMDB
KuvanMeSH, HMDB
Phenylalanine hydroxylase cofactorMeSH, HMDB
Sapropterin dihydrochlorideMeSH, HMDB
tetrahydro-6-BiopterinMeSH, HMDB
2',4',5'-TrihydroxybutyrophenoneMeSH
SapropterinMeSH
TrihydroxybutyrophenoneMeSH
1-Butanone, 1-(2,4,5-trihydroxyphenyl)MeSH
2,4,5-TrihydroxybutyrophenoneMeSH
(6R)-5,6,7,8-Tetrahydro-L-biopterinHMDB
(6R)-5,6,7,8-TetrahydrobiopterinHMDB
(6R)-TetrahydrobiopterinHMDB
2-Amino-6-(1,2-dihydroxypropyl)-5,6,7,8-tetrahydro-4(3H)-pteridinoneHMDB
6R-Tetrahydro-L-biopterinHMDB
6beta-5,6,7,8-Tetrahydro-L-biopterinHMDB
6β-5,6,7,8-Tetrahydro-L-biopterinHMDB
L-erythro-TetrahydrobiopterinHMDB
(6R)-2-Amino-6-[(1R,2S)-1,2-dihydroxypropyl]-5,6,7,8-tetrahydro-4(1H)-pteridinoneHMDB
Chemical FormulaC9H15N5O3
Average Molecular Mass241.247 g/mol
Monoisotopic Mass241.117 g/mol
CAS Registry Number62989-33-7
IUPAC Name(6R)-2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-1,4,5,6,7,8-hexahydropteridin-4-one
Traditional Nametetrahydrobiopterin
SMILESC[C@H](O)[C@H](O)C1CNC2=C(N1)C(=O)N=C(N)N2
InChI IdentifierInChI=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 KeyFNKQXYHWGSIFBK-BYAPIUGTSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as biopterins and derivatives. These are coenzymes containing a 2-amino-pteridine-4-one derivative. They are mainly synthesized in several parts of the body, including the pineal gland.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPteridines and derivatives
Sub ClassPterins and derivatives
Direct ParentBiopterins and derivatives
Alternative Parents
Substituents
  • Biopterin
  • Aminopyrimidine
  • Pyrimidone
  • Secondary aliphatic/aromatic amine
  • Pyrimidine
  • 1,3-aminoalcohol
  • Vinylogous amide
  • Heteroaromatic compound
  • Secondary alcohol
  • 1,2-diol
  • 1,2-aminoalcohol
  • Secondary amine
  • Azacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.21 g/LALOGPS
logP-1.7ALOGPS
logP-2.7ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)13.52ChemAxon
pKa (Strongest Basic)1.58ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area132 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity68.43 m³·mol⁻¹ChemAxon
Polarizability23.67 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-014i-5900000000-804847492ab49a9a85fcNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-03di-3019000000-70dd873f93868fd0cb17Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-006x-0090000000-241111b39335d9a7d02dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01bl-0980000000-a6b56555596f17eb9943Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01dj-1900000000-337483f746fd21c54572Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0290000000-5db8572d378da978b669Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0007-0930000000-4e48e429709976699df9Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9600000000-8474626666ad84477dd8Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
2095.0Log mg/kg[1200:3700]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
272Alimentary tract and metabolism productsHealthcare, pharmaceuticals & veterinary productsNot Available
Pathways
0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Phenylalanine-4-hydroxylase structureClick to view 3D structurePhenylalanine-4-hydroxylaseP00439HumansPredicted (SEA)0.0778492
Click to view 3D structureNitric oxide synthase 3Q28969Sus scrofaPredicted (SEA)0.155698
Dihydrofolate synthase/folylpolyglutamate synthase structureClick to view 3D structureDihydrofolate synthase/folylpolyglutamate synthaseP08192Escherichia coli (strain K12)Predicted (SEA)15.6477
Click to view 3D structureSolute carrier organic anion transporter family member 1A3P70502Rattus norvegicusPredicted (SEA)17.2047
Nitric oxide synthase 3 structureClick to view 3D structureNitric oxide synthase 3P29474HumansPredicted (SEA)143.943
Nitric oxide synthase 1 structureClick to view 3D structureNitric oxide synthase 1P29475HumansPredicted (SEA)377.102
Nitric oxide synthase, inducible structureClick to view 3D structureNitric oxide synthase, inducibleP35228HumansPredicted (SEA)221.715
Dihydrofolate reductase structureClick to view 3D structureDihydrofolate reductaseP00374HumansPredicted (SEA)1614.75
Gastrotropin structureClick to view 3D structureGastrotropinP51161HumansPredicted (SEA)21.2528
Click to view 3D structureSerine/threonine protein kinase UL97P16788HHV-5Predicted (SEA)12.7673
Click to view 3D structureXanthine dehydrogenaseO54050Rhodobacter capsulatusPredicted (SEA)8.87481
Dihydrofolate reductase structureClick to view 3D structureDihydrofolate reductaseP0ABQ4Escherichia coli (strain K12)Predicted (SEA)1269.88
Click to view 3D structureHypoxanthine-guanine phosphoribosyltransferaseP9WHQ9Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)Predicted (SEA)29.1935
Cyclin-dependent kinase 2 structureClick to view 3D structureCyclin-dependent kinase 2P24941HumansPredicted (SEA)7324.99
Dihydropteroate synthase structureClick to view 3D structureDihydropteroate synthaseP0AC13Escherichia coli (strain K12)Predicted (SEA)65.0041
Click to view 3D structureCyclic di-GMP phosphodiesterase RocRQ9HX69Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG12228)Predicted (SEA)46.6317
Click to view 3D structureRYamide receptorP25931Drosophila melanogasterPredicted (SEA)5.99439
Thymidylate synthase structureClick to view 3D structureThymidylate synthaseP04818HumansPredicted (SEA)1444.41
Cyclin-dependent kinase 1 structureClick to view 3D structureCyclin-dependent kinase 1P06493HumansPredicted (SEA)7242.7
Purine nucleoside phosphorylase structureClick to view 3D structurePurine nucleoside phosphorylaseP00491HumansPredicted (SEA)91.3171
2-amino-4-hydroxy-6-hydroxymethyldihydropteridine pyrophosphokinase structureClick to view 3D structure2-amino-4-hydroxy-6-hydroxymethyldihydropteridine pyrophosphokinaseP26281Escherichia coli (strain K12)Predicted (SEA)35.11
Click to view 3D structureBifunctional dihydrofolate reductase-thymidylate synthaseQ07422Toxoplasma gondiiPredicted (SEA)2239.72
Click to view 3D structureThymidylate synthaseC3SWJ7Escherichia coliPredicted (SEA)645.526
Click to view 3D structureProton-coupled folate transporterQ96NT5HumansPredicted (SEA)424.278
Folate receptor alpha structureClick to view 3D structureFolate receptor alphaP15328HumansPredicted (SEA)438.68
Concentrations
Not Available
External Links
DrugBank IDDB00360
HMDB IDHMDB0059658
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDCPD-14053
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkSapropterin
Chemspider ID40270
ChEBI ID59560
PubChem Compound ID44257
Kegg Compound IDC00272
YMDB IDNot Available
ECMDB IDECMDB24177
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10333495
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=1297822
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=16510994
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=19627172
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=21466737
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=21646032
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=22110560
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=22112818
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=22310224
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=22388642
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=22391997
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=22575621
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=22832064
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=23235653
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=23266371
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=23430527
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=23430545
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=23436109
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=23462988
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=23690520
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=23705856
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=23712020
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=23743404
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=4004257