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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:21 UTC
HMDB IDHMDB00787
Secondary Accession NumbersNone
Metabolite Identification
Common NameSapropterin
DescriptionSapropterin is converted from 7,8-dihydroneopterin triphosphate by 6-pyruvoyl tetrahydropterin synthase and sepiapterin reductase. It is essential in the formation of neurotransmitters and for nitric oxide synthase (PMID 16946131 ).
Structure
Thumb
Synonyms
ValueSource
L-erythro-TetrahydrobiopterinChEBI
(6R)-5,6,7,8-tetrahydro-L-BiopterinHMDB
(6R)-5,6,7,8-TetrahydrobiopterinHMDB
(6R)-L-erythro-5,6,7,8-TetrahydrobiopterinHMDB
(6R)-L-erythro-TetrahydrobiopterinHMDB
(6R)-TetrahydrobiopterinHMDB
6b-5,6,7,8-tetrahydro-L-BiopterinHMDB
6R-BH4HMDB
6R-tetrahydro-L-BiopterinHMDB
R-THBPHMDB
[6R-[6R*(1R*,2S*)]]-2-amino-6-(1,2-dihydroxypropyl)-5,6,7,8-tetrahydro-4(1H)-pteridinoneHMDB
Chemical FormulaC9H15N5O3
Average Molecular Weight241.2471
Monoisotopic Molecular Weight241.117489371
IUPAC Name2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-1,4,5,6,7,8-hexahydropteridin-4-one
Traditional Name2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-5,6,7,8-tetrahydro-1H-pteridin-4-one
CAS Registry Number62989-33-7
SMILES
C[C@H](O)[C@H](O)C1CNC2=C(N1)C(=O)N=C(N)N2
InChI Identifier
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 KeyInChIKey=FNKQXYHWGSIFBK-BYAPIUGTSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Secondary aliphatic/aromatic amine
  • Pyrimidone
  • Pyrimidine
  • Primary aromatic amine
  • Heteroaromatic compound
  • Vinylogous amide
  • 1,3-aminoalcohol
  • Secondary alcohol
  • 1,2-diol
  • 1,2-aminoalcohol
  • Azacycle
  • Secondary amine
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.21 mg/mLALOGPS
logP-1.7ALOGPS
logP-2.7ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)10.01ChemAxon
pKa (Strongest Basic)3.58ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area132 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity68.43 m3·mol-1ChemAxon
Polarizability23.69 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Aromatic L-Aminoacid Decarboxylase DeficiencySMP00170Not Available
Catecholamine BiosynthesisSMP00012map00350
Tyrosine hydroxylase deficiencySMP00497Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0110 +/- 0.0008 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.026 (0.014-0.038) uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0099 +/- 0.0008 uMAdult (>18 years old)BothSmoking details
Associated Disorders and Diseases
Disease References
Smoking
  1. Ueda S, Matsuoka H, Miyazaki H, Usui M, Okuda S, Imaizumi T: Tetrahydrobiopterin restores endothelial function in long-term smokers. J Am Coll Cardiol. 2000 Jan;35(1):71-5. [10636262 ]
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022243
KNApSAcK IDNot Available
Chemspider ID7991951
KEGG Compound IDC00272
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00787
Metagene LinkHMDB00787
METLIN ID5753
PubChem Compound9816201
PDB IDNot Available
ChEBI ID64491
References
Synthesis ReferenceKatoh, Setsuko; Akino, Miki. Biosynthesis of tetrahydrobiopterin in animals. Zoological Science (1986), 3(5), 745-57.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Toda Y, Mori K, Hashimoto T, Miyazaki M, Nozaki S, Watanabe Y, Kuroda Y, Kagami S: Administration of secretin for autism alters dopamine metabolism in the central nervous system. Brain Dev. 2006 Mar;28(2):99-103. Epub 2005 Sep 15. [16168596 ]
  2. Moens AL, Kass DA: Tetrahydrobiopterin and cardiovascular disease. Arterioscler Thromb Vasc Biol. 2006 Nov;26(11):2439-44. Epub 2006 Aug 31. [16946131 ]
  3. Komori H, Matsuishi T, Yamada S, Yamashita Y, Ohtaki E, Kato H: Cerebrospinal fluid biopterin and biogenic amine metabolites during oral R-THBP therapy for infantile autism. J Autism Dev Disord. 1995 Apr;25(2):183-93. [7559284 ]

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Plays an important role in the physiology of adrenergic neurons.
Gene Name:
TH
Uniprot ID:
P07101
Molecular weight:
55611.26
General function:
Involved in amino acid binding
Specific function:
Not Available
Gene Name:
PAH
Uniprot ID:
P00439
Molecular weight:
51861.565
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the final one or two reductions in tetra-hydrobiopterin biosynthesis to form 5,6,7,8-tetrahydrobiopterin.
Gene Name:
SPR
Uniprot ID:
P35270
Molecular weight:
28048.13
General function:
Involved in amino acid binding
Specific function:
Not Available
Gene Name:
TPH1
Uniprot ID:
P17752
Molecular weight:
50984.725
General function:
Involved in amino acid binding
Specific function:
Not Available
Gene Name:
TPH2
Uniprot ID:
Q8IWU9
Molecular weight:
56056.295
General function:
Involved in oxidoreductase activity
Specific function:
The product of this enzyme, tetrahydrobiopterin (BH-4), is an essential cofactor for phenylalanine, tyrosine, and tryptophan hydroxylases.
Gene Name:
QDPR
Uniprot ID:
P09417
Molecular weight:
25789.295
General function:
Involved in oxidoreductase activity
Specific function:
Produces nitric oxide (NO) which is implicated in vascular smooth muscle relaxation through a cGMP-mediated signal transduction pathway. NO mediates vascular endothelial growth factor (VEGF)-induced angiogenesis in coronary vessels and promotes blood clotting through the activation of platelets. Isoform eNOS13C: Lacks eNOS activity, dominant-negative form that may down-regulate eNOS activity by forming heterodimers with isoform 1.
Gene Name:
NOS3
Uniprot ID:
P29474
Molecular weight:
133273.59