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Record Information
Version2.0
Created at2022-09-12 01:48:51 UTC
Updated at2022-09-12 01:48:51 UTC
NP-MRD IDNP0322813
Secondary Accession NumbersNone
Natural Product Identification
Common Name5-hydroxy-10-(1-hydroxypropyl)-2,2-dimethyl-6-(3-methylbutanoyl)pyrano[2,3-f]chromen-8-one
Description5-Hydroxy-10-(1-hydroxypropyl)-2,2-dimethyl-6-(3-methylbutanoyl)-2H,8H-pyrano[2,3-h]chromen-8-one belongs to the class of organic compounds known as angular pyranocoumarins. These are organic compounds containing a pyran (or a hydrogenated derivative) angularly fused to a coumarin moiety. 5-hydroxy-10-(1-hydroxypropyl)-2,2-dimethyl-6-(3-methylbutanoyl)pyrano[2,3-f]chromen-8-one is found in Mesua assamica. 5-Hydroxy-10-(1-hydroxypropyl)-2,2-dimethyl-6-(3-methylbutanoyl)-2H,8H-pyrano[2,3-h]chromen-8-one is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC22H26O6
Average Mass386.4440 Da
Monoisotopic Mass386.17294 Da
IUPAC Name5-hydroxy-10-(1-hydroxypropyl)-2,2-dimethyl-6-(3-methylbutanoyl)-2H,8H-pyrano[2,3-f]chromen-8-one
Traditional Name5-hydroxy-10-(1-hydroxypropyl)-2,2-dimethyl-6-(3-methylbutanoyl)pyrano[2,3-f]chromen-8-one
CAS Registry NumberNot Available
SMILES
CCC(O)C1=CC(=O)OC2=C(C(=O)CC(C)C)C(O)=C3C=CC(C)(C)OC3=C12
InChI Identifier
InChI=1S/C22H26O6/c1-6-14(23)13-10-16(25)27-21-17(13)20-12(7-8-22(4,5)28-20)19(26)18(21)15(24)9-11(2)3/h7-8,10-11,14,23,26H,6,9H2,1-5H3
InChI KeyKGIZIVCWFFPHEN-UHFFFAOYSA-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
Mesua assamicaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as angular pyranocoumarins. These are organic compounds containing a pyran (or a hydrogenated derivative) angularly fused to a coumarin moiety.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassPyranocoumarins
Direct ParentAngular pyranocoumarins
Alternative Parents
Substituents
  • Angular pyranocoumarin
  • 2,2-dimethyl-1-benzopyran
  • Butyrophenone
  • Benzopyran
  • 1-benzopyran
  • Aryl alkyl ketone
  • Aryl ketone
  • Alkyl aryl ether
  • Pyranone
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous acid
  • Secondary alcohol
  • Lactone
  • Ketone
  • Oxacycle
  • Ether
  • Organoheterocyclic compound
  • Aromatic alcohol
  • Alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen 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
logP3.49ALOGPS
logP3.98ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)7.42ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area93.06 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity107.1 m³·mol⁻¹ChemAxon
Polarizability41.8 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 Compound75071148
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]