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Record Information
Version3.6
Creation Date2006-05-22 14:17:34 UTC
Update Date2016-02-11 01:05:15 UTC
HMDB IDHMDB02065
Secondary Accession NumbersNone
Metabolite Identification
Common Name6-Lactoyltetrahydropterin
Description6-Lactoyltetrahydropterin is a putative intermediate in the de novo synthesis of tetrahydrobiopterin (BH4) pathway, in a reaction involving the enzyme sepiapterin reductase (E.C. 1.1.1.153) in human liver. In brain, an enzyme distinct from sepiapterin reductase catalyzes the TPNH-dependent reduction of 6-pyruvoyl-tetrahydropterin to 6-lactoyl-tetrahydropterin. (PMID: 4004850 ). In brain, the expression of other enzymes involved in BH4 biosynthesis includes aldose reductase, carbonyl reductase, GTP-cyclohydrolase I, and 6-pyruvoyltetrahydrobiopterin. Sepiapterin reductase expression is increased in Parkinson's disease brain tissue. (PMID: 17270157 ).
Structure
Thumb
Synonyms
ValueSource
2-amino-6-Lactoyl-5,6,7,8-tetrahydropteridin-4(3H)-oneChEBI
6-1'-oxo-2'-Hydroxypropyl tetrahydropterinChEBI
6-LactoyltetrahydropterinChEBI
6-Lactoyl tetrahydropterinHMDB
Lactoyl-H4-pterinHMDB
Lactoyl-PH4HMDB
Chemical FormulaC9H13N5O3
Average Molecular Weight239.2312
Monoisotopic Molecular Weight239.101839307
IUPAC Name2-amino-6-(2-hydroxypropanoyl)-3,4,5,6,7,8-hexahydropteridin-4-one
Traditional Name6-lactoyl tetrahydropterin
CAS Registry Number33405-80-0
SMILES
CC(O)C(=O)C1CNC2=C(N1)C(=O)NC(N)=N2
InChI Identifier
InChI=1S/C9H13N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h3-4,12,15H,2H2,1H3,(H4,10,11,13,14,17)
InChI KeyInChIKey=HKCYZTKHPLJZDR-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as pterins and derivatives. These are polycyclic aromatic compounds containing a pterin moiety, which consist of a pteridine ring bearing a ketone and an amine group to form 2-aminopteridin-4(3H)-one.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPteridines and derivatives
Sub ClassPterins and derivatives
Direct ParentPterins and derivatives
Alternative Parents
Substituents
  • Pterin
  • Secondary aliphatic/aromatic amine
  • Pyrimidone
  • Pyrimidine
  • Primary aromatic amine
  • Beta-aminoketone
  • Acyloin
  • Heteroaromatic compound
  • Vinylogous amide
  • Alpha-hydroxy ketone
  • Alpha-aminoketone
  • 1,3-aminoalcohol
  • Secondary alcohol
  • Ketone
  • Azacycle
  • Secondary amine
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusExpected but not 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 Solubility1.21 mg/mLALOGPS
logP-1.6ALOGPS
logP-1.7ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)11.12ChemAxon
pKa (Strongest Basic)4.62ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area128.84 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity67.87 m3·mol-1ChemAxon
Polarizability22.59 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 LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Dopa-responsive dystoniaSMP00486Not Available
Hyperphenylalaniemia due to guanosine triphosphate cyclohydrolase deficiencySMP00487Not Available
Hyperphenylalaninemia due to 6-pyruvoyltetrahydropterin synthase deficiency (ptps)SMP00488Not Available
Hyperphenylalaninemia due to dhpr-deficiencySMP00489Not Available
Pterine BiosynthesisSMP00005map00790
Segawa syndromeSMP00490Not Available
Sepiapterin reductase deficiencySMP00491Not 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 IDFDB022828
KNApSAcK IDNot Available
Chemspider ID148245
KEGG Compound IDC04244
BioCyc ID6-LACTOYL-5678-TETRAHYDROPTERIN
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB02065
Metagene LinkHMDB02065
METLIN ID6468
PubChem Compound169508
PDB IDNot Available
ChEBI ID17248
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Milstien S, Kaufman S: Biosynthesis of tetrahydrobiopterin: conversion of dihydroneopterin triphosphate to tetrahydropterin intermediates. Biochem Biophys Res Commun. 1985 May 16;128(3):1099-107. [4004850 ]
  2. Tobin JE, Cui J, Wilk JB, Latourelle JC, Laramie JM, McKee AC, Guttman M, Karamohamed S, DeStefano AL, Myers RH: Sepiapterin reductase expression is increased in Parkinson's disease brain tissue. Brain Res. 2007 Mar 30;1139:42-7. Epub 2007 Jan 8. [17270157 ]

Enzymes

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 → 6-Lactoyltetrahydropterin + NADPH + Hydrogen Iondetails
6-Lactoyltetrahydropterin + NADP → Dyspropterin + NADPH + Hydrogen Iondetails