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Record Information
Version2.0
Created at2022-09-10 04:42:25 UTC
Updated at2022-09-10 04:42:25 UTC
NP-MRD IDNP0295622
Secondary Accession NumbersNone
Natural Product Identification
Common Name[(1r,3s,4ar,10ar)-9-hydroxy-1-methyl-5,10-dioxo-1h,3h,4h,4ah,10ah-naphtho[2,3-c]pyran-3-yl]acetic acid
Description2-[(1R,3S,4aR,10aR)-9-hydroxy-1-methyl-5,10-dioxo-1H,3H,4H,4aH,5H,10H,10aH-naphtho[2,3-c]pyran-3-yl]acetic acid belongs to the class of organic compounds known as naphthopyranones. Naphthopyranones are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system. [(1r,3s,4ar,10ar)-9-hydroxy-1-methyl-5,10-dioxo-1h,3h,4h,4ah,10ah-naphtho[2,3-c]pyran-3-yl]acetic acid is found in Streptomyces tanashiensis. Based on a literature review very few articles have been published on 2-[(1R,3S,4aR,10aR)-9-hydroxy-1-methyl-5,10-dioxo-1H,3H,4H,4aH,5H,10H,10aH-naphtho[2,3-c]pyran-3-yl]acetic acid.
Structure
Thumb
Synonyms
ValueSource
2-[(1R,3S,4AR,10ar)-9-hydroxy-1-methyl-5,10-dioxo-1H,3H,4H,4ah,5H,10H,10ah-naphtho[2,3-c]pyran-3-yl]acetateGenerator
Chemical FormulaC16H16O6
Average Mass304.2980 Da
Monoisotopic Mass304.09469 Da
IUPAC Name2-[(1R,3S,4aR,10aR)-9-hydroxy-1-methyl-5,10-dioxo-1H,3H,4H,4aH,5H,10H,10aH-naphtho[2,3-c]pyran-3-yl]acetic acid
Traditional Name[(1R,3S,4aR,10aR)-9-hydroxy-1-methyl-5,10-dioxo-1H,3H,4H,4aH,10aH-naphtho[2,3-c]pyran-3-yl]acetic acid
CAS Registry NumberNot Available
SMILES
C[C@H]1O[C@H](CC(O)=O)C[C@@H]2[C@H]1C(=O)C1=C(O)C=CC=C1C2=O
InChI Identifier
InChI=1S/C16H16O6/c1-7-13-10(5-8(22-7)6-12(18)19)15(20)9-3-2-4-11(17)14(9)16(13)21/h2-4,7-8,10,13,17H,5-6H2,1H3,(H,18,19)/t7-,8+,10-,13+/m1/s1
InChI KeyIRONHSFDHVKJAJ-HUZBHQLSSA-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
Streptomyces tanashiensisLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as naphthopyranones. Naphthopyranones are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassNaphthopyrans
Sub ClassNaphthopyranones
Direct ParentNaphthopyranones
Alternative Parents
Substituents
  • Naphthopyranone
  • Naphthoquinone
  • Naphthalene
  • Tetralin
  • Quinone
  • Aryl ketone
  • Aryl alkyl ketone
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • Benzenoid
  • Pyran
  • Oxane
  • Vinylogous acid
  • Ketone
  • Oxacycle
  • Carboxylic acid
  • Dialkyl ether
  • Ether
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxygen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
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
logP1.65ChemAxon
pKa (Strongest Acidic)3.53ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area100.9 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity75.91 m³·mol⁻¹ChemAxon
Polarizability29.69 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound163194006
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]