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Record Information
Version1.0
Created at2022-09-05 20:29:28 UTC
Updated at2022-09-05 20:29:29 UTC
NP-MRD IDNP0219486
Secondary Accession NumbersNone
Natural Product Identification
Common Name(3r,4r)-6-methoxy-1-oxo-3-pentyl-3,4-dihydro-2-benzopyran-4-yl acetate
Description(3R,4R)-(-)-6-methoxy-1-oxo-3-n-pentyl-3,4-dihydro-1H-isochromen-4-yl-acetate belongs to the class of organic compounds known as 2-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 2-position (3R,4R)-(-)-6-methoxy-1-oxo-3-n-pentyl-3,4-dihydro-1H-isochromen-4-yl-acetate is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. It was first documented in 2008 (PMID: 17870137). Based on a literature review very few articles have been published on (3R,4R)-(-)-6-methoxy-1-oxo-3-n-pentyl-3,4-dihydro-1H-isochromen-4-yl-acetate.
Structure
Thumb
Synonyms
ValueSource
(3R,4R)-(-)-6-Methoxy-3,4-dihydro-4-acetoxy-5-N-pentyl-1H-2-benzopyran-1-oneChEBI
(3R,4R)-(-)-6-Methoxy-1-oxo-3-N-pentyl-3,4-dihydro-1H-isochromen-4-yl-acetic acidGenerator
Chemical FormulaC17H22O5
Average Mass306.3580 Da
Monoisotopic Mass306.14672 Da
IUPAC Name(3R,4R)-6-methoxy-1-oxo-3-pentyl-3,4-dihydro-1H-2-benzopyran-4-yl acetate
Traditional Name(3R,4R)-6-methoxy-1-oxo-3-pentyl-3,4-dihydro-2-benzopyran-4-yl acetate
CAS Registry NumberNot Available
SMILES
CCCCC[C@H]1OC(=O)C2=CC=C(OC)C=C2[C@H]1OC(C)=O
InChI Identifier
InChI=1S/C17H22O5/c1-4-5-6-7-15-16(21-11(2)18)14-10-12(20-3)8-9-13(14)17(19)22-15/h8-10,15-16H,4-7H2,1-3H3/t15-,16-/m1/s1
InChI KeyXFZDFYYRUDDKBS-HZPDHXFCSA-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 OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 2-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 2-position.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzopyrans
Sub Class2-benzopyrans
Direct Parent2-benzopyrans
Alternative Parents
Substituents
  • 2-benzopyran
  • Anisole
  • Alkyl aryl ether
  • Dicarboxylic acid or derivatives
  • Benzenoid
  • Carboxylic acid ester
  • Lactone
  • Carboxylic acid derivative
  • Oxacycle
  • Ether
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Organooxygen compound
  • 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
logP3.45ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area61.83 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity80.96 m³·mol⁻¹ChemAxon
Polarizability33.3 ųChemAxon
Number of Rings2ChemAxon
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 ID24721597
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound24796588
PDB IDNot Available
ChEBI ID66698
Good Scents IDNot Available
References
General References
  1. Guimaraes KG, de Souza Filho JD, Dos Mares-Guia TR, Braga FC: Dihydroisocoumarin from Xyris pterygoblephara active against dermatophyte fungi. Phytochemistry. 2008 Jan;69(2):439-44. doi: 10.1016/j.phytochem.2007.08.002. Epub 2007 Sep 17. [PubMed:17870137 ]
  2. LOTUS database [Link]