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Record Information
Version4.0
Creation Date2012-10-30 10:32:48 UTC
Update Date2017-09-27 08:43:23 UTC
HMDB IDHMDB0059658
Secondary Accession Numbers
  • HMDB59658
Metabolite Identification
Common NameL-erythro-tetrahydrobiopterin
DescriptionL-erythro-tetrahydrobiopterin is part of the Folate biosynthesis pathway. It is a substrate for: Sepiapterin reductase.
Structure
Thumb
Synonyms
ValueSource
(-)-(6R)-2-amino-6-((1R,2S)-1,2-Dihydroxypropyl)-5,6,7,8-tetrahydro-4(3H)-pteridinoneChEBI
(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
5,6,7,8-tetrahydro-L-ErythrobiopterinMeSH
5,6,7,8-Tetrahydrobiopterin, (S-(r*,s*))-isomerMeSH
5,6,7,8-TetrahydrodictyopterinMeSH
6R-L-erythro-5,6,7,8-TetrahydrobiopterinMeSH
BPH4MeSH
D-threo-TetrahydrobiopterinMeSH
THBPMeSH
KuvanMeSH
Phenylalanine hydroxylase cofactorMeSH
Sapropterin dihydrochlorideMeSH
tetrahydro-6-BiopterinMeSH
Chemical FormulaC9H15N5O3
Average Molecular Weight241.2471
Monoisotopic Molecular Weight241.117489371
IUPAC Name(6R)-2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-3,4,5,6,7,8-hexahydropteridin-4-one
Traditional Name6R-5,6,7,8-tetrahydrobiopterin
CAS Registry NumberNot Available
SMILES
[H][C@@]1(CNC2=C(N1)C(=O)NC(N)=N2)[C@@H](O)[C@H](C)O
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 KeyFNKQXYHWGSIFBK-RPDRRWSUSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassPteridines and derivatives
Direct ParentBiopterins and derivatives
Alternative Parents
Substituents
  • Biopterin
  • Aminopyrimidine
  • Secondary aliphatic/aromatic amine
  • Pyrimidone
  • Primary aromatic amine
  • Pyrimidine
  • 1,3-aminoalcohol
  • Heteroaromatic compound
  • Vinylogous amide
  • 1,2-aminoalcohol
  • 1,2-diol
  • Secondary alcohol
  • Azacycle
  • Secondary amine
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Amine
  • Alcohol
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Role

Industrial application:

  Pharmaceutical industry:

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 Solubility2.83 g/LALOGPS
logP-1.8ALOGPS
logP-2.3ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)11.12ChemAxon
pKa (Strongest Basic)4.61ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area132 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity68.63 m³·mol⁻¹ChemAxon
Polarizability23.61 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (6 TMS)splash10-0zfr-2921300000-63bf6ee58b9df85919f6View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-0zfr-2921300000-63bf6ee58b9df85919f6View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006x-0090000000-e6b01d1139ccb3c6338dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gi3-0980000000-8963ef41f1138b05a813View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00xr-1900000000-bcfa359703563c696c0fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0390000000-4810efa20f31adea3824View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006y-1930000000-5b32feeb643e238bb159View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9400000000-a7dbebeb1df4ea110948View in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Phenylalanine and Tyrosine MetabolismPw000042Pw000042 greyscalePw000042 simpleMap00360
PhenylketonuriaPw000119Pw000119 greyscalePw000119 simpleNot Available
Tyrosinemia Type 2 (or Richner-Hanhart syndrome)Pw000120Pw000120 greyscalePw000120 simpleNot Available
Tyrosinemia Type 3 (TYRO3)Pw000121Pw000121 greyscalePw000121 simpleNot Available
Displaying all 4 entries
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID40270
KEGG Compound IDC00272
BioCyc IDCPD-14053
BiGG IDNot Available
Wikipedia LinkSapropterin
METLIN IDNot Available
PubChem Compound44257
PDB IDNot Available
ChEBI ID59560
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

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
Reactions
L-Tyrosine + L-erythro-tetrahydrobiopterin + Oxygen → L-Dopa + 4a-Hydroxytetrahydrobiopterindetails
L-erythro-tetrahydrobiopterin + L-Tyrosine + Oxygen → L-Dopa + 4a-Carbinolamine tetrahydrobiopterin + Waterdetails
General function:
Involved in amino acid binding
Specific function:
Not Available
Gene Name:
PAH
Uniprot ID:
P00439
Molecular weight:
51861.565
Reactions
L-Phenylalanine + L-erythro-tetrahydrobiopterin + Oxygen → L-Tyrosine + 4a-Hydroxytetrahydrobiopterindetails
L-erythro-tetrahydrobiopterin + L-Phenylalanine + Oxygen → 4a-Carbinolamine tetrahydrobiopterin + L-Tyrosine + Waterdetails
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
Reactions
L-erythro-tetrahydrobiopterin + NADP → Dyspropterin + NADPHdetails
L-erythro-tetrahydrobiopterin + NADP → 6-Lactoyltetrahydropterin + NADPH + Hydrogen Iondetails
General function:
Involved in amino acid binding
Specific function:
Not Available
Gene Name:
TPH1
Uniprot ID:
P17752
Molecular weight:
50984.725
Reactions
L-Tryptophan + L-erythro-tetrahydrobiopterin + Oxygen → Oxitriptan + 4a-Hydroxytetrahydrobiopterindetails
L-erythro-tetrahydrobiopterin + L-Tryptophan + Oxygen → Oxitriptan + 4a-Carbinolamine tetrahydrobiopterin + Waterdetails
General function:
Involved in amino acid binding
Specific function:
Not Available
Gene Name:
TPH2
Uniprot ID:
Q8IWU9
Molecular weight:
56056.295
Reactions
L-Tryptophan + L-erythro-tetrahydrobiopterin + Oxygen → Oxitriptan + 4a-Hydroxytetrahydrobiopterindetails
L-erythro-tetrahydrobiopterin + L-Tryptophan + Oxygen → Oxitriptan + 4a-Carbinolamine tetrahydrobiopterin + Waterdetails
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
Reactions
4a-Carbinolamine tetrahydrobiopterin + NADH + Hydrogen Ion → L-erythro-tetrahydrobiopterin + NADdetails
4a-Carbinolamine tetrahydrobiopterin + NADPH + Hydrogen Ion → L-erythro-tetrahydrobiopterin + NADPdetails
General function:
Not Available
Specific function:
Glyceryl-ether monooxygenase that cleaves the O-alkyl bond of ether lipids. Ether lipids are essential components of brain membranes.
Gene Name:
AGMO
Uniprot ID:
Q6ZNB7
Molecular weight:
51499.41
Reactions
1-alkyl-sn-glycerol + L-erythro-tetrahydrobiopterin + Oxygen → 1-O-alkyl-sn-glycerol + Dihydrobiopterin + Waterdetails