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Record Information
Version2.0
Created at2022-09-05 21:21:36 UTC
Updated at2022-09-05 21:21:36 UTC
NP-MRD IDNP0220134
Secondary Accession NumbersNone
Natural Product Identification
Common Name1-(6-methoxy-6-methylhept-4-en-2-yl)-3a,6,6,9b,11a-pentamethyl-1h,2h,3h,3bh,4h,7h,8h,9h,9ah,10h,11h-cyclopenta[a]phenanthrene-4,7-diol
Description14-(6-Methoxy-6-methylhept-4-en-2-yl)-1,6,6,11,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-7-ene-5,9-diol belongs to the class of organic compounds known as cucurbitacins. These are polycyclic compounds containing the tetracyclic cucurbitane nucleus skeleton, 19-(10->9b)-abeo-10alanost-5-ene (also known as 9b-methyl-19-nor lanosta-5-ene), with a variety of oxygenation functionalities at different positions. 1-(6-methoxy-6-methylhept-4-en-2-yl)-3a,6,6,9b,11a-pentamethyl-1h,2h,3h,3bh,4h,7h,8h,9h,9ah,10h,11h-cyclopenta[a]phenanthrene-4,7-diol is found in Momordica charantia. 14-(6-Methoxy-6-methylhept-4-en-2-yl)-1,6,6,11,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-7-ene-5,9-diol is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC31H52O3
Average Mass472.7540 Da
Monoisotopic Mass472.39165 Da
IUPAC Name14-(6-methoxy-6-methylhept-4-en-2-yl)-1,6,6,11,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-5,9-diol
Traditional Name14-(6-methoxy-6-methylhept-4-en-2-yl)-1,6,6,11,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-5,9-diol
CAS Registry NumberNot Available
SMILES
COC(C)(C)C=CCC(C)C1CCC2(C)C3C(O)C=C4C(CCC(O)C4(C)C)C3(C)CCC12C
InChI Identifier
InChI=1S/C31H52O3/c1-20(11-10-15-27(2,3)34-9)21-14-16-31(8)26-24(32)19-23-22(12-13-25(33)28(23,4)5)29(26,6)17-18-30(21,31)7/h10,15,19-22,24-26,32-33H,11-14,16-18H2,1-9H3
InChI KeyJITGKINHLQAZRO-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
Momordica charantiaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cucurbitacins. These are polycyclic compounds containing the tetracyclic cucurbitane nucleus skeleton, 19-(10->9b)-abeo-10alanost-5-ene (also known as 9b-methyl-19-nor lanosta-5-ene), with a variety of oxygenation functionalities at different positions.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassCucurbitacins
Direct ParentCucurbitacins
Alternative Parents
Substituents
  • Cucurbitacin skeleton
  • Triterpenoid
  • 7-hydroxysteroid
  • 3-hydroxysteroid
  • Hydroxysteroid
  • 3-hydroxy-delta-5-steroid
  • Delta-5-steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Ether
  • Dialkyl ether
  • Organooxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic 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
logP6.6ALOGPS
logP5.97ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)19.41ChemAxon
pKa (Strongest Basic)-0.42ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.69 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity142.95 m³·mol⁻¹ChemAxon
Polarizability58.27 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
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 Compound73236884
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]