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Record Information
Version2.0
Created at2022-09-09 23:52:41 UTC
Updated at2022-09-09 23:52:41 UTC
NP-MRD IDNP0292375
Secondary Accession NumbersNone
Natural Product Identification
Common Name5-hydroxy-1'',6'',8''-trimethyl-2'',5''-dioxodispiro[bis(oxolane)-3,2':5',7''-[3]oxatricyclo[6.3.1.0⁴,¹²]dodecan]-6''-yl acetate
Description5-Hydroxy-1'',6'',8''-trimethyl-2'',5''-dioxodispiro[bis(oxolane)-3,2':5',7''-[3]Oxatricyclo[6.3.1.0⁴,¹²]Dodecane]-6''-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). 5-hydroxy-1'',6'',8''-trimethyl-2'',5''-dioxodispiro[bis(oxolane)-3,2':5',7''-[3]oxatricyclo[6.3.1.0⁴,¹²]dodecan]-6''-yl acetate is found in Leonurus cardiaca. 5-Hydroxy-1'',6'',8''-trimethyl-2'',5''-dioxodispiro[bis(oxolane)-3,2':5',7''-[3]Oxatricyclo[6.3.1.0⁴,¹²]Dodecane]-6''-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
Synonyms
ValueSource
5-Hydroxy-1'',6'',8''-trimethyl-2'',5''-dioxodispiro[bis(oxolane)-3,2':5',7''-[3]oxatricyclo[6.3.1.0,]dodecane]-6''-yl acetic acidGenerator
5-Hydroxy-1'',6'',8''-trimethyl-2'',5''-dioxodispiro[bis(oxolane)-3,2':5',7''-[3]oxatricyclo[6.3.1.0⁴,¹²]dodecane]-6''-yl acetic acidGenerator
Chemical FormulaC22H30O8
Average Mass422.4740 Da
Monoisotopic Mass422.19407 Da
IUPAC Name5-hydroxy-1'',6'',8''-trimethyl-2'',5''-dioxodispiro[bis(oxolane)-3,2':5',7''-[3]oxatricyclo[6.3.1.0⁴,¹²]dodecane]-6''-yl acetate
Traditional Name5-hydroxy-1'',6'',8''-trimethyl-2'',5''-dioxodispiro[bis(oxolane)-3,2':5',7''-[3]oxatricyclo[6.3.1.0⁴,¹²]dodecane]-6''-yl acetate
CAS Registry NumberNot Available
SMILES
CC(=O)OC1(C)C(=O)C2OC(=O)C3(C)CCCC(C)(C23)C11CCC2(COC(O)C2)O1
InChI Identifier
InChI=1S/C22H30O8/c1-12(23)29-20(4)16(25)14-15-18(2,17(26)28-14)6-5-7-19(15,3)22(20)9-8-21(30-22)10-13(24)27-11-21/h13-15,24H,5-11H2,1-4H3
InChI KeyYPFSOWQXNOLVDV-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
Leonurus cardiacaLOTUS 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
  • Gamma butyrolactone
  • Tetrahydrofuran
  • Carboxylic acid ester
  • Hemiacetal
  • Ketone
  • Lactone
  • Carboxylic acid derivative
  • Ether
  • Dialkyl ether
  • Oxacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic 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
logP1.27ALOGPS
logP2.17ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)12.37ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area108.36 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity100.75 m³·mol⁻¹ChemAxon
Polarizability42.48 ųChemAxon
Number of Rings5ChemAxon
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 Compound14158700
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]