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Record Information
Version2.0
Created at2022-09-10 01:49:30 UTC
Updated at2022-09-10 01:49:31 UTC
NP-MRD IDNP0293686
Secondary Accession NumbersNone
Natural Product Identification
Common Name1-{5-[1-(acetyloxy)tridecyl]oxolan-2-yl}-13-(5-methyl-2-oxo-5h-furan-3-yl)tridecyl acetate
Description1-{5-[1-(Acetyloxy)tridecyl]oxolan-2-yl}-13-(5-methyl-2-oxo-2,5-dihydrofuran-3-yl)tridecyl acetate belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain. 1-{5-[1-(acetyloxy)tridecyl]oxolan-2-yl}-13-(5-methyl-2-oxo-5h-furan-3-yl)tridecyl acetate is found in Annona muricata. 1-{5-[1-(Acetyloxy)tridecyl]oxolan-2-yl}-13-(5-methyl-2-oxo-2,5-dihydrofuran-3-yl)tridecyl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
Synonyms
ValueSource
1-{5-[1-(acetyloxy)tridecyl]oxolan-2-yl}-13-(5-methyl-2-oxo-2,5-dihydrofuran-3-yl)tridecyl acetic acidGenerator
Chemical FormulaC39H68O7
Average Mass648.9660 Da
Monoisotopic Mass648.49650 Da
IUPAC Name1-{5-[1-(acetyloxy)tridecyl]oxolan-2-yl}-13-(5-methyl-2-oxo-2,5-dihydrofuran-3-yl)tridecyl acetate
Traditional Name1-{5-[1-(acetyloxy)tridecyl]oxolan-2-yl}-13-(5-methyl-2-oxo-5H-furan-3-yl)tridecyl acetate
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCC(OC(C)=O)C1CCC(O1)C(CCCCCCCCCCCCC1=CC(C)OC1=O)OC(C)=O
InChI Identifier
InChI=1S/C39H68O7/c1-5-6-7-8-9-10-14-17-20-23-26-35(44-32(3)40)37-28-29-38(46-37)36(45-33(4)41)27-24-21-18-15-12-11-13-16-19-22-25-34-30-31(2)43-39(34)42/h30-31,35-38H,5-29H2,1-4H3
InChI KeyPSTPUNZWIKIYNV-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
Annona muricataLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty alcohols
Direct ParentAnnonaceous acetogenins
Alternative Parents
Substituents
  • Annonaceae acetogenin skeleton
  • Fatty alcohol ester
  • Tricarboxylic acid or derivatives
  • 2-furanone
  • Dihydrofuran
  • Tetrahydrofuran
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Carboxylic acid ester
  • Lactone
  • Oxacycle
  • Ether
  • Dialkyl ether
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organooxygen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic 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
logP8.97ALOGPS
logP11.36ChemAxon
logS-7.5ALOGPS
pKa (Strongest Acidic)13.47ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area88.13 ŲChemAxon
Rotatable Bond Count30ChemAxon
Refractivity184.31 m³·mol⁻¹ChemAxon
Polarizability82.25 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
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 IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]