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Record Information
Version2.0
Created at2022-09-10 13:46:22 UTC
Updated at2022-09-10 13:46:23 UTC
NP-MRD IDNP0301041
Secondary Accession NumbersNone
Natural Product Identification
Common Name2,4-dihydroxy-6-methyl-8-[(2s,3s,4r)-2,3,4,5-tetrahydroxypentyl]pteridin-7-one
Description6-Methyl-7-oxo-8-(1-D-ribityl)lumazine (2-oxo tautomer), also known as photolumazine C or 7-hydroxy-6-methyl-8-(1-D-ribityl)lumazine, belongs to the class of organic compounds known as pteridines and derivatives. These are polycyclic aromatic compounds containing a pteridine moiety, which consists of a pyrimidine fused to a pyrazine ring to form pyrimido(4,5-b)pyrazine. 2,4-dihydroxy-6-methyl-8-[(2s,3s,4r)-2,3,4,5-tetrahydroxypentyl]pteridin-7-one is found in Formica polyctena and Russula emetica. Based on a literature review very few articles have been published on 6-methyl-7-oxo-8-(1-D-ribityl)lumazine (2-oxo tautomer).
Structure
Thumb
Synonyms
ValueSource
Photolumazine CChEBI
7-Hydroxy-6-methyl-8-(1-D-ribityl)lumazineMeSH
6-Methyl-7-hydroxyribolumazineMeSH
Chemical FormulaC12H16N4O7
Average Mass328.2810 Da
Monoisotopic Mass328.10190 Da
IUPAC Name2,4-dihydroxy-6-methyl-8-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]-7,8-dihydropteridin-7-one
Traditional Name2,4-dihydroxy-6-methyl-8-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]pteridin-7-one
CAS Registry NumberNot Available
SMILES
CC1=NC2=C(O)N=C(O)N=C2N(C[C@H](O)[C@H](O)[C@H](O)CO)C1=O
InChI Identifier
InChI=1S/C12H16N4O7/c1-4-11(22)16(2-5(18)8(20)6(19)3-17)9-7(13-4)10(21)15-12(23)14-9/h5-6,8,17-20H,2-3H2,1H3,(H2,14,15,21,23)/t5-,6+,8-/m0/s1
InChI KeyQCYVUUAIJUUUPI-BBVRLYRLSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Formica polyctenaLOTUS Database
Russula emeticaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pteridines and derivatives. These are polycyclic aromatic compounds containing a pteridine moiety, which consists of a pyrimidine fused to a pyrazine ring to form pyrimido(4,5-b)pyrazine.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPteridines and derivatives
Sub ClassNot Available
Direct ParentPteridines and derivatives
Alternative Parents
Substituents
  • Pteridine
  • Pyrimidone
  • Pyrazine
  • Pyrimidine
  • Vinylogous amide
  • Heteroaromatic compound
  • Urea
  • Secondary alcohol
  • Lactam
  • Azacycle
  • Polyol
  • Alcohol
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2.2ChemAxon
pKa (Strongest Acidic)10.74ChemAxon
pKa (Strongest Basic)-1.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area179.83 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity77.45 m³·mol⁻¹ChemAxon
Polarizability30.26 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID389705
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440869
PDB IDNot Available
ChEBI ID60900
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]