2'-Deoxysepiapterin (CHEM034838)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:15:55 UTC
Update Date2016-11-09 01:21:12 UTC
Accession NumberCHEM034838
Identification
Common Name2'-Deoxysepiapterin
ClassSmall Molecule
Description2'-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) [HMDB]
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-Amino-7,8-dihydro-6-(1-oxopropyl)-4(1H)-pteridinHMDB
2-Amino-7,8-dihydro-6-propionyl-4(3H)-pteridinoneHMDB
DeoxysepiapterinHMDB
IsosepiapterinHMDB
Chemical FormulaC9H11N5O2
Average Molecular Mass221.216 g/mol
Monoisotopic Mass221.091 g/mol
CAS Registry Number1797-87-1
IUPAC Name2-amino-6-propanoyl-1,4,7,8-tetrahydropteridin-4-one
Traditional Name2-amino-6-propanoyl-7,8-dihydro-1H-pteridin-4-one
SMILESCCC(=O)C1=NC2=C(NC1)NC(N)=NC2=O
InChI IdentifierInChI=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 KeyMXQYRFPIGKAGPW-UHFFFAOYSA-N
Chemical Taxonomy
Description 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
  • Aminopyrimidine
  • Pyrimidone
  • Secondary aliphatic/aromatic amine
  • Pyrimidine
  • Heteroaromatic compound
  • Vinylogous amide
  • Ketimine
  • Ketone
  • Propargyl-type 1,3-dipolar organic compound
  • Secondary amine
  • Organic 1,3-dipolar compound
  • Azacycle
  • 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
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility1 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity65.93 m³·mol⁻¹ChemAxon
Polarizability21.67 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-08i0-4900000000-a8e7ae80998be3cd5fbbSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0090000000-57b858bb6190a8ce9e99Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-2790000000-d5d1d80e350bedff2f87Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01vk-4900000000-974d9809a6eeb3bc71d2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0290000000-15fcc62eae66b0f30015Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006x-3960000000-b9d338c33d1e86e76a70Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9200000000-695020ff3c5215b6f94eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03k9-0950000000-aebd1c6a85be31e11ae0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006x-0910000000-904542c89f779c60705aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9400000000-09cde025a3be59f8e3bfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0090000000-3180cf5bc92aa7bfafd1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01b9-0940000000-63494505a00cd69a6956Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001j-7900000000-c15579616e4c7f7e463dSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0000389
FooDB IDFDB022007
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID13628076
ChEBI ID166566
PubChem Compound ID14055971
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. 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.
2. 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.
3. 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.
4. 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.
5. Fukushima T, Nixon JC: Analysis of reduced forms of biopterin in biological tissues and fluids. Anal Biochem. 1980 Feb;102(1):176-88.
6. Fukushima T, Nixon JC: Chromatographic analysis of pteridines. Methods Enzymol. 1980;66:429-36.
7. Fukushima T, Nixon JC: Anaerobic degradation of pteridines and purines by intestinal organisms. Appl Environ Microbiol. 1980 Aug;40(2):244-8.