Common Name |
6-Lactoyltetrahydropterin
Description |
6-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 Parkinsons disease brain tissue. (PMID: 17270157 ).
Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms |
Value |
Source |
2-amino-6-Lactoyl-5,6,7,8-tetrahydropteridin-4(3H)-oneChEBI
6-1'-oxo-2'-Hydroxypropyl tetrahydropterinChEBI
6-Lactoyl tetrahydropterinHMDB
6-Lactoyl-5,6,7,8-tetrahydropterinHMDB
Lactoyl-H4-pterinHMDB
Lactoyl-PH4HMDB
1'-oxo-2'-Hydroxypropyl-tetrahydropterinMeSH
Chemical Formlia |
C9H13N5O3
Average Molecliar Weight |
239.2312
Monoisotopic Molecliar Weight |
239.101839307
IUPAC Name |
2-amino-6-(2-hydroxypropanoyl)-3,4,5,6,7,8-hexahydropteridin-4-one
Traditional Name |
6-lactoyl tetrahydropterin
CAS Registry Number |
33405-80-0
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 Key |
HKCYZTKHPLJZDR-UHFFFAOYSA-N
Chemical Taxonomy |
Description |
This compound belongs to the class of chemical entities 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.
Kingdom |
Chemical entities
Super Class |
Organic compounds
Class |
Organoheterocyclic compounds
Sub Class |
Pteridines and derivatives
Direct Parent |
Pterins and derivatives
Alternative Parents |
Secondary alkylarylamines
Pyrimidones
Aminopyrimidines and derivatives
Primary aromatic amines
Acyloins
Vinylogous amides
Heteroaromatic compounds
Alpha-hydroxy ketones
Alpha-amino ketones
1,3-aminoalcohols
Secondary alcohols
Azacyclic compounds
Organopnictogen compounds
Organic oxides
Hydrocarbon derivatives
Substituents |
Pterin
Aminopyrimidine
Secondary aliphatic/aromatic amine
Pyrimidone
Acyloin
Primary aromatic amine
Pyrimidine
1,3-aminoalcohol
Alpha-aminoketone
Alpha-hydroxy ketone
Heteroaromatic compound
Vinylogous amide
Ketone
Secondary alcohol
Azacycle
Secondary amine
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Amine
Organic oxide
Organopnictogen compound
Alcohol
Primary amine
Organic oxygen compound
Aromatic heteropolycyclic compound
Molecliar Framework |
Aromatic heteropolycyclic compounds
External Descriptors |
tetrahydropterin (CHEBI:17248 )
a small moleclie (6-LACTOYL-5678-TETRAHYDROPTERIN )
Ontology |
Status |
Expected but not Quantified
Origin |
Endogenous
Biofunction |
Not Available
Application |
Not Available
Cellliar locations |
Cytoplasm (predicted from logP)
Physical Properties |
State |
Solid
Experimental Properties |
Property |
Value |
Reference |
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties |
Property |
Value |
Source |
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
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
Spectra |
Spectra |
Not Available
Biological Properties |
Cellliar Locations |
Cytoplasm (predicted from logP)
Biofluid Locations |
Not Available
Tissue Location |
Not Available
Pathways |
Name |
SMPDB Link |
KEGG 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 References |
None
Associated OMIM IDs |
None
External Links |
DrugBank ID |
Not Available
DrugBank Metabolite ID |
Not Available
Phenol Explorer Compound ID |
Not Available
Phenol Explorer Metabolite ID |
Not Available
FoodDB ID |
FDB022828
KNApSAcK ID |
Not Available
Chemspider ID |
148245
KEGG Compound ID |
C04244
BioCyc ID |
6-LACTOYL-5678-TETRAHYDROPTERIN
BiGG ID |
Not Available
Wikipedia Link |
Not Available
NuGOwiki Link |
HMDB02065
Metagene Link |
HMDB02065
METLIN ID |
6468
PubChem Compound |
169508
PDB ID |
Not Available
ChEBI ID |
17248
Product: Ozanimod
References |
Synthesis Reference |
Not Available |
Material Safety Data Sheet (MSDS) |
Not Available |
General References |
- 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. [PubMed:4004850 ]
- 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 Parkinsons disease brain tissue. Brain Res. 2007 Mar 30;1139:42-7. Epub 2007 Jan 8. [PubMed: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 Ion |
details |
6-Lactoyltetrahydropterin + NADP → Dyspropterin + NADPH + Hydrogen Ion |
details |
PMID: 23285225