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Record Information
Version3.6
Creation Date2012-10-30 10:32:48 UTC
Update Date2016-02-11 07:50:25 UTC
HMDB IDHMDB59658
Secondary Accession NumbersNone
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
L-erythro-TetrahydrobiopterinChEBI
R-THBPChEBI
SapropterinaChEBI
SapropterinumChEBI
TetrahydrobiopterinChEBI
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@@](C)(O)[C@]([H])(O)[C@@]1([H])CNC2=C(N1)C(O)=NC(=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-RPDRRWSUSA-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
  • Imidolactam
  • Pyrimidine
  • Primary aromatic amine
  • Heteroaromatic compound
  • Vinylogous amide
  • 1,3-aminoalcohol
  • Secondary alcohol
  • Lactam
  • 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
StatusExpected but not Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity68.63 m3·mol-1ChemAxon
Polarizability23.61 Å3ChemAxon
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
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 LinkKEGG Link
Phenylalanine and Tyrosine MetabolismSMP00008map00360
PhenylketonuriaSMP00206Not Available
Tyrosinemia Type 2 (or Richner-Hanhart syndrome)SMP00369Not Available
Tyrosinemia Type 3 (TYRO3)SMP00370Not Available
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 IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB59658
Metagene LinkHMDB59658
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