| 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