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Showing Compound Tetrahydrobiopterin (FDB021880)

Record Information
Version1.0
Creation date2011-09-21 00:04:26 UTC
Update date2015-07-21 06:56:49 UTC
Primary IDFDB021880
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameTetrahydrobiopterin
DescriptionTetrahydrobiopterin or BH4 is a cofactor in the synthesis of nitric oxide. It is also essential in the conversion of phenylalanine to tyrosine by the enzyme phenylalanine-4-hydroxylase; the conversion of tyrosine to L-dopa by the enzyme tyrosine hydroxylase; and conversion of tryptophan to 5-hydroxytryptophan via tryptophan hydroxylase. A defect in BH4 production and/or a defect in the enzyme dihydropteridine reductase (DHPR) causes phenylketonuria type IV, as well as dopa-responsive dystonias. -- Wikipedia. [HMDB]
CAS Number17528-72-2
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
2-Amino-6-(1,2-dihydroxypropyl)-5,6,7,8-tetrahydoro-4(1H)-pteridinoneChEBI
BH4ChEBI
(1R,2S)-(2-Amino-3,4,5,6,7,8-hexahydro-4-oxo-6-pteridinyl)-1,2-propandiolHMDB
2-Amino-6-(1,2-dihydroxypropyl)-5,6,7,8-tetrahydoro-4(1H)-5,6,7,8-tetrahydro-2-amino-6-(1,2-dihydroxypropyl)-4(1H)-pteridinoneHMDB
2-Amino-6-(1,2-dihydroxypropyl)-5,6,7,8-tetrahydro-4(1H)-pteridinoneHMDB
5,6,7,8-Erythro-tetrahydrobiopterinHMDB
5,6,7,8-Tetra-H-biopterinHMDB
5,6,7,8-Tetrahydro-2-amino-6-(1,2-dihydroxypropyl)-4(1H)-pteridinoneHMDB
5,6,7,8-TetrahydrobiopterinHMDB
L-Erythro-2-amino-6-(1,2-dihydroxypropyl)-5,6,7,8-tetrahydro-4(3H)-pteridinonHMDB
Tetra-H-biopterinHMDB
Tetra-hydro-biopterinHMDB
5,6,7,8-TetrahydrodictyopterinHMDB
6R-BH4HMDB
6R-L-Erythro-5,6,7,8-tetrahydrobiopterinHMDB
THBPHMDB
5,6,7,8-Tetrahydrobiopterin, (S-(r*,s*))-isomerHMDB
BPH4HMDB
D-Threo-tetrahydrobiopterinHMDB
5,6,7,8-Tetrahydro-L-erythrobiopterinHMDB
Sapropterin dihydrochlorideHMDB
Tetrahydro-6-biopterinHMDB
KuvanHMDB
Phenylalanine hydroxylase cofactorHMDB
SapropterinHMDB
1-Butanone, 1-(2,4,5-trihydroxyphenyl)HMDB
2,4,5-TrihydroxybutyrophenoneHMDB
TrihydroxybutyrophenoneHMDB
2',4',5'-TrihydroxybutyrophenoneHMDB
2-Amino-6-(1,2-dihydroxypropyl)-5,6,7,8-tetrahydoro-4(1H)-5,6,7,8-Tetrahydro-2-amino-6-(1,2-dihydroxypropyl)-4(1H)-pteridinonehmdb
2-amino-6-(1,2-Dihydroxypropyl)-5,6,7,8-tetrahydoro-4(1H)-pteridinoneChEBI
2-amino-6-(1,2-dihydroxypropyl)-5,6,7,8-tetrahydro-4(1H)-Pteridinonehmdb
5,6,7,8-erythro-tetrahydrobiopterinhmdb
5,6,7,8-tetra-H-biopterinhmdb
L-erythro-2-Amino-6-(1,2-dihydroxypropyl)-5,6,7,8-tetrahydro-4(3H)-pteridinonhmdb
tetra-H-biopterinhmdb
tetra-hydro-biopterinhmdb
Tetrahydrobiopterinhmdb
Predicted Properties
PropertyValueSource
Water Solubility2.21 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity68.43 m³·mol⁻¹ChemAxon
Polarizability23.4 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC9H15N5O3
IUPAC name2-amino-6-(1,2-dihydroxypropyl)-1,4,5,6,7,8-hexahydropteridin-4-one
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)
InChI KeyFNKQXYHWGSIFBK-UHFFFAOYSA-N
Isomeric SMILESCC(O)C(O)C1CNC2=C(N1)C(=O)N=C(N)N2
Average Molecular Weight241.2471
Monoisotopic Molecular Weight241.117489371
Classification
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
Ontology
Physiological effect

Health effect:

Disposition

Source:

Biological location:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSTetrahydrobiopterin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-014i-5900000000-804847492ab49a9a85fcSpectrum
Predicted GC-MSTetrahydrobiopterin, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000i-8095000000-47f102cc1afbed04012fSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006x-0090000000-241111b39335d9a7d02dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01bl-0980000000-a6b56555596f17eb9943Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01dj-1900000000-337483f746fd21c54572Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0290000000-5db8572d378da978b669Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0007-0930000000-4e48e429709976699df9Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9600000000-8474626666ad84477dd8Spectrum
NMRNot Available
ChemSpider ID1093
ChEMBL IDCHEMBL337765
KEGG Compound IDC00272
Pubchem Compound ID1125
Pubchem Substance IDNot Available
ChEBI ID15372
Phenol-Explorer IDNot Available
DrugBank IDDB00360
HMDB IDHMDB00027
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID34464
KNApSAcK IDNot Available
HET ID1DF1
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDTetrahydrobiopterin
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Tyrosine 3-monooxygenaseTHP07101
Phenylalanine-4-hydroxylasePAHP00439
Tryptophan 5-hydroxylase 1TPH1P17752
Tryptophan 5-hydroxylase 2TPH2Q8IWU9
Pterin-4-alpha-carbinolamine dehydratasePCBD1P61457
Sepiapterin reductaseSPRP35270
Pathways
NameSMPDB LinkKEGG Link
Pterine BiosynthesisSMP00005 map00790
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference