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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-26 21:22:08 UTC
HMDB IDHMDB0000389
Secondary Accession Numbers
  • HMDB00389
Metabolite Identification
Common Name2'-Deoxysepiapterin
Description2'-Deoxysepiapterin, also known as isosepiapterin, 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. 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). 2'-Deoxysepiapterin is a strong basic compound (based on its pKa).
Structure
Data?1582752128
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 Weight221.2159
Monoisotopic Molecular Weight221.091274621
IUPAC Name2-amino-6-propanoyl-1,4,7,8-tetrahydropteridin-4-one
Traditional Name2-amino-6-propanoyl-7,8-dihydro-1H-pteridin-4-one
CAS Registry Number1797-87-1
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 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
Ontology
Disposition

Source:

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 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-08i0-4900000000-a8e7ae80998be3cd5fbbSpectrum
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
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022007
KNApSAcK IDNot Available
Chemspider ID13628076
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14055971
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceBaur, 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
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. Fukushima T, Nixon JC: Chromatographic analysis of pteridines. Methods Enzymol. 1980;66:429-36. [PubMed:7374483 ]
  6. Fukushima T, Nixon JC: Anaerobic degradation of pteridines and purines by intestinal organisms. Appl Environ Microbiol. 1980 Aug;40(2):244-8. [PubMed:7469409 ]