Record Information
Version1.0
Creation date2011-09-21 00:05:04 UTC
Update date2015-10-09 22:30:49 UTC
Primary IDFDB021914
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameSepiapterin
DescriptionSepiapterin, also known as lopac-S-154, 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. Sepiapterin is an extremely weak basic (essentially neutral) compound (based on its pKa). Sepiapterin is a potentially toxic compound. Sepiapterin, with regard to humans, has been linked to the inborn metabolic disorder sepiapterin reductase deficiency.
CAS Number17094-01-8
Structure
Thumb
Synonyms
SynonymSource
(S)-2-Amino-7,8-dihydro-6-(2-hydroxy-1-oxopropyl)-4(1H)-pteridinoneHMDB
1-(2-Amino-7,8-dihydro-4-hydroxy-6-pteridinyl)-2-hydroxy-1-propanoneHMDB
2-Amino-6-(S)-lactoyl-7,8-dihydro-4(3H)-pteridinoneHMDB
2-Amino-7,8-dihydro-6-[(2S)-2-hydroxy-1-oxopropyl]-4(1H)pteridinoneHMDB
L-SepiapterinHMDB
Lopac-S-154HMDB
SepiapterineHMDB
Sepiapterin-CHMDB
2-Amino-6-(S)-lactoyl-7,8-dihydro-4(3H)- pteridinoneHMDB
Sepia-pterinHMDB
2-Amino-7,8-dihydro-6-((2S)-2-hydroxy-1-oxopropyl)-4(3H)-pteridinone acidHMDB
(S)-2-amino-7,8-dihydro-6-(2-hydroxy-1-oxopropyl)-4(1H)-Pteridinonehmdb
1-(2-amino-7,8-dihydro-4-hydroxy-6-pteridinyl)-2-hydroxy-1-Propanonehmdb
2-amino-7,8-dihydro-6-[(2S)-2-hydroxy-1-oxopropyl]-4(1H)Pteridinonehmdb
L-sepiapterinhmdb
Sepiapterinhmdb
Predicted Properties
PropertyValueSource
Water Solubility1.18 g/LALOGPS
logP-1.1ALOGPS
logP-1.4ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)9.18ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area129.17 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity67.5 m³·mol⁻¹ChemAxon
Polarizability22.44 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC9H11N5O3
IUPAC name2-amino-6-[(2S)-2-hydroxypropanoyl]-1,4,7,8-tetrahydropteridin-4-one
InChI IdentifierInChI=1S/C9H11N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h3,15H,2H2,1H3,(H4,10,11,13,14,17)/t3-/m0/s1
InChI KeyVPVOXUSPXFPWBN-VKHMYHEASA-N
Isomeric SMILESC[C@H](O)C(=O)C1=NC2=C(NC1)NC(N)=NC2=O
Average Molecular Weight237.2153
Monoisotopic Molecular Weight237.086189243
Classification
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
  • Acyloin
  • Pyrimidine
  • Alpha-hydroxy ketone
  • Heteroaromatic compound
  • Vinylogous amide
  • Secondary alcohol
  • Ketimine
  • Ketone
  • Propargyl-type 1,3-dipolar organic compound
  • Secondary amine
  • Azacycle
  • Organic 1,3-dipolar compound
  • Alcohol
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxide
  • Imine
  • Carbonyl group
  • Organic oxygen compound
  • Amine
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location:

Source:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-5910000000-428f8e46f66f7bfd3119JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-000j-6590000000-f5711e35dabd2148a990JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00ko-0950000000-2cf5caf622d639c89359JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0297-2900000000-f9fe1627a36e71b61db6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00di-3900000000-82cabe6461c502831c78JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0079-0090000000-1e9c5af672b8662896afJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0940000000-1e5701cfd0eed57e783eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03k9-2910000000-3e376e485f9ccca285f4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0290000000-9eff7a7965f178fa7e5eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-1920000000-a634b611cb12a5f44b6bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006x-9200000000-ddd484b0e0f2ed7d6cd7JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
ChemSpider ID58746
ChEMBL IDCHEMBL1255653
KEGG Compound IDC00835
Pubchem Compound ID65253
Pubchem Substance IDNot Available
ChEBI ID16095
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00238
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Sepiapterin reductaseSPRP35270
14-3-3 protein zeta/deltaYWHAZP63104
14-3-3 protein beta/alphaYWHABP31946
14-3-3 protein gammaYWHAGP61981
Pathways
NameSMPDB LinkKEGG Link
Pterine BiosynthesisSMP00005 map00790
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference