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Record Information
Version2.0
Created at2022-09-12 08:11:58 UTC
Updated at2022-09-12 08:11:58 UTC
NP-MRD IDNP0326545
Secondary Accession NumbersNone
Natural Product Identification
Common Name12-(acetyloxy)-2-hydroxy-5-isopropyl-6,9-dimethyl-3-oxo-15-oxatetracyclo[7.6.1.0²,⁶.0¹³,¹⁶]hexadeca-1(16),13-dien-4-yl acetate
Description4-(Acetyloxy)-2-hydroxy-6,9-dimethyl-3-oxo-5-(propan-2-yl)-15-oxatetracyclo[7.6.1.0²,⁶.0¹³,¹⁶]Hexadeca-1(16),13-dien-12-yl acetate belongs to the class of organic compounds known as alpha-acyloxy ketones. These are ketones that have an acyloxy substituent alpha to the carbonyl group. They have the general structure R4C(=O)OC(R2)(R3)C(R1)=O (R1=organyl, R4=H or organyl; R2,R3 = any atom). 12-(acetyloxy)-2-hydroxy-5-isopropyl-6,9-dimethyl-3-oxo-15-oxatetracyclo[7.6.1.0²,⁶.0¹³,¹⁶]hexadeca-1(16),13-dien-4-yl acetate is found in Coprinellus heptemerus. 4-(Acetyloxy)-2-hydroxy-6,9-dimethyl-3-oxo-5-(propan-2-yl)-15-oxatetracyclo[7.6.1.0²,⁶.0¹³,¹⁶]Hexadeca-1(16),13-dien-12-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
Synonyms
ValueSource
4-(Acetyloxy)-2-hydroxy-6,9-dimethyl-3-oxo-5-(propan-2-yl)-15-oxatetracyclo[7.6.1.0,.0,]hexadeca-1(16),13-dien-12-yl acetic acidGenerator
4-(Acetyloxy)-2-hydroxy-6,9-dimethyl-3-oxo-5-(propan-2-yl)-15-oxatetracyclo[7.6.1.0²,⁶.0¹³,¹⁶]hexadeca-1(16),13-dien-12-yl acetic acidGenerator
Chemical FormulaC24H32O7
Average Mass432.5130 Da
Monoisotopic Mass432.21480 Da
IUPAC Name12-(acetyloxy)-2-hydroxy-6,9-dimethyl-3-oxo-5-(propan-2-yl)-15-oxatetracyclo[7.6.1.0²,⁶.0¹³,¹⁶]hexadeca-1(16),13-dien-4-yl acetate
Traditional Name12-(acetyloxy)-2-hydroxy-5-isopropyl-6,9-dimethyl-3-oxo-15-oxatetracyclo[7.6.1.0²,⁶.0¹³,¹⁶]hexadeca-1(16),13-dien-4-yl acetate
CAS Registry NumberNot Available
SMILES
CC(C)C1C(OC(C)=O)C(=O)C2(O)C3=C4C(=CO3)C(CCC4(C)CCC12C)OC(C)=O
InChI Identifier
InChI=1S/C24H32O7/c1-12(2)17-19(31-14(4)26)20(27)24(28)21-18-15(11-29-21)16(30-13(3)25)7-8-22(18,5)9-10-23(17,24)6/h11-12,16-17,19,28H,7-10H2,1-6H3
InChI KeyZIKZQHFSXRIGND-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
Coprinellus heptemerusLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha-acyloxy ketones. These are ketones that have an acyloxy substituent alpha to the carbonyl group. They have the general structure R4C(=O)OC(R2)(R3)C(R1)=O (R1=organyl, R4=H or organyl; R2,R3 = any atom).
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlpha-acyloxy ketones
Alternative Parents
Substituents
  • Alpha-acyloxy ketone
  • Dicarboxylic acid or derivatives
  • Heteroaromatic compound
  • Tertiary alcohol
  • Furan
  • Cyclic alcohol
  • Ketone
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Organic oxide
  • Hydrocarbon derivative
  • Alcohol
  • 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
logP3.21ALOGPS
logP3.23ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)11.09ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area103.04 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity110.61 m³·mol⁻¹ChemAxon
Polarizability46.66 ųChemAxon
Number of Rings4ChemAxon
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 Compound85421851
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]