| Common Name |
2-Deoxysepiapterin
| Description |
2-Deoxysepiapterin is a metabolite of the catabolism of tetrahydrobiopterin, present in variable amounts in various human biofluids (blood, urine, feces) and tissues (kidney, liver, adrenal, brain, and blood). (PMID 6638488 , 7356152 , 7374483 ) 2-Deoxysepiapterin can also be degraded or catabolized by microorganisms located within the cecal contents (PMID 7469409 ).
| Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
2-amino-7,8-dihydro-6-(1-Oxopropyl)-4(1H)-pteridinHMDB
2-amino-7,8-dihydro-6-Propionyl-4(3H)-pteridinoneHMDB
DeoxysepiapterinHMDB
IsosepiapterinHMDB
| Chemical Formlia |
C9H11N5O2
| Average Molecliar Weight |
221.2159
| Monoisotopic Molecliar Weight |
221.091274621
| IUPAC Name |
2-amino-6-propanoyl-1,4,7,8-tetrahydropteridin-4-one
| Traditional Name |
2-amino-6-propanoyl-7,8-dihydro-1H-pteridin-4-one
| CAS Registry Number |
1797-87-1
| SMILES |
CCC(=O)C1=NC2=C(NC1)NC(N)=NC2=O
| InChI Identifier |
InChI=1S/C9H11N5O2/c1-2-5(15)4-3-11-7-6(12-4)8(16)14-9(10)13-7/h2-3H2,1H3,(H4,10,11,13,14,16)
| InChI Key |
MXQYRFPIGKAGPW-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
Vinylogous amides
Heteroaromatic compounds
Ketones
Ketimines
Propargyl-type 1,3-dipolar organic compounds
Azacyclic compounds
Organopnictogen compounds
Organic oxides
Hydrocarbon derivatives
| Substituents |
Pterin
Aminopyrimidine
Pyrimidone
Secondary aliphatic/aromatic amine
Primary aromatic amine
Pyrimidine
Heteroaromatic compound
Vinylogous amide
Ketimine
Ketone
Azacycle
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Amine
Imine
Carbonyl group
Aromatic heteropolycyclic compound
| Molecliar Framework |
Aromatic heteropolycyclic compounds
| External Descriptors |
Not Available
| Ontology |
| Status |
Expected but not Quantified
| Origin |
Endogenous
| Biofunction |
Not Available
| Application |
Not Available
| Cellliar locations |
Not Available
| 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 Solubility1.0 mg/mLALOGPS
logP-0.39ALOGPS
logP-0.42ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)7.93ChemAxon
pKa (Strongest Basic)3.16ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area108.94 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity65.93 m3·mol-1ChemAxon
Polarizability21.67 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
| Spectrum Type |
Description |
Splash Key |
|
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, Positivesplash10-00di-0090000000-57b858bb6190a8ce9e99View in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, Positivesplash10-00di-2790000000-d5d1d80e350bedff2f87View in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, Positivesplash10-01vk-4900000000-974d9809a6eeb3bc71d2View in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, Negativesplash10-00di-0290000000-15fcc62eae66b0f30015View in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, Negativesplash10-006x-3960000000-b9d338c33d1e86e76a70View in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, Negativesplash10-052f-9200000000-695020ff3c5215b6f94eView in MoNA
| Biological Properties |
| Cellliar Locations |
Not Available
| Biofluid Locations |
Not Available
| Tissue Location |
Not Available
| Pathways |
Not 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 |
FDB022007
| KNApSAcK ID |
Not Available
| Chemspider ID |
13628076
| KEGG Compound ID |
Not Available
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB00389
| Metagene Link |
HMDB00389
| METLIN ID |
Not Available
| PubChem Compound |
14055971
| PDB ID |
Not Available
| ChEBI ID |
Not Available
Product: CDD3505
References |
| Synthesis Reference |
Baur, Ralph; Sugimoto, Takashi; Pfleiderer, Wolfgang. Pteridines. LXXXV. Chemical synthesis of deoxysepiapterin and 6-acylpteridines by acyl radical substitution reactions. Helvetica Chimica Acta (1988), 71(3), 531-43. |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
- Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30. [PubMed:12829005 ]
- Yamamoto T, Moriwaki Y, Takahashi S, Ohata H, Nakano T, Yamakita J, Higashino K: Effect of glucagon on the xylitol-induced increase in the plasma concentration and urinary excretion of purine bases. Metabolism. 1996 Nov;45(11):1354-9. [PubMed:8931639 ]
- Andondonskaja-Renz B, Zeitler HJ: Separation of pteridines from blood cells and plasma by reverse-phase high-performance liquid chromatography. Anal Biochem. 1983 Aug;133(1):68-78. [PubMed:6638488 ]
- Fukushima T, Nixon JC: Analysis of reduced forms of biopterin in biological tissues and fluids. Anal Biochem. 1980 Feb;102(1):176-88. [PubMed:7356152 ]
- Fukushima T, Nixon JC: Chromatographic analysis of pteridines. Methods Enzymol. 1980;66:429-36. [PubMed:7374483 ]
- Fukushima T, Nixon JC: Anaerobic degradation of pteridines and purines by intestinal organisms. Appl Environ Microbiol. 1980 Aug;40(2):244-8. [PubMed:7469409 ]
|
PMID: 1433178