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Record Information
Version1.0
Created at2022-09-12 01:40:19 UTC
Updated at2022-09-12 01:40:19 UTC
NP-MRD IDNP0322729
Secondary Accession NumbersNone
Natural Product Identification
Common Name11-[(benzoyloxy)methyl]-5,6-dihydroxy-3,7,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-4-yl benzoate
Description[4-(Benzoyloxy)-5,6-dihydroxy-3,7,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]Pentadeca-2,7-dien-11-yl]methyl benzoate belongs to the class of organic compounds known as tigliane and ingenane diterpenoids. These are diterpenoids containing the tigliane or ingenane carbon skeleton. The tigliane skeleton is a tetracyclic ring that consists of the 4/7/6/3 ring junction. It is derived from casbane by 6,10- and 5,14-cyclizations and is a framework of phorbol. The ingenane skeleton is derived by rearrangement of tigliane. 11-[(benzoyloxy)methyl]-5,6-dihydroxy-3,7,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-4-yl benzoate is found in Euphorbia portulacoides. [4-(Benzoyloxy)-5,6-dihydroxy-3,7,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]Pentadeca-2,7-dien-11-yl]methyl benzoate is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
Synonyms
ValueSource
[4-(Benzoyloxy)-5,6-dihydroxy-3,7,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0,.0,]pentadeca-2,7-dien-11-yl]methyl benzoic acidGenerator
[4-(Benzoyloxy)-5,6-dihydroxy-3,7,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-11-yl]methyl benzoic acidGenerator
Chemical FormulaC34H36O7
Average Mass556.6550 Da
Monoisotopic Mass556.24610 Da
IUPAC Name11-[(benzoyloxy)methyl]-5,6-dihydroxy-3,7,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-4-yl benzoate
Traditional Name11-[(benzoyloxy)methyl]-5,6-dihydroxy-3,7,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-4-yl benzoate
CAS Registry NumberNot Available
SMILES
CC1CC2C(C3C=C(C)C(O)C4(O)C(OC(=O)C5=CC=CC=C5)C(C)=CC14C3=O)C2(C)COC(=O)C1=CC=CC=C1
InChI Identifier
InChI=1S/C34H36O7/c1-19-15-24-26-25(32(26,4)18-40-30(37)22-11-7-5-8-12-22)16-21(3)33(28(24)36)17-20(2)29(34(33,39)27(19)35)41-31(38)23-13-9-6-10-14-23/h5-15,17,21,24-27,29,35,39H,16,18H2,1-4H3
InChI KeyRTKRAQUFZMFZSV-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
Euphorbia portulacoidesLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as tigliane and ingenane diterpenoids. These are diterpenoids containing the tigliane or ingenane carbon skeleton. The tigliane skeleton is a tetracyclic ring that consists of the 4/7/6/3 ring junction. It is derived from casbane by 6,10- and 5,14-cyclizations and is a framework of phorbol. The ingenane skeleton is derived by rearrangement of tigliane.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassDiterpenoids
Direct ParentTigliane and ingenane diterpenoids
Alternative Parents
Substituents
  • Ingenane diterpenoid
  • Benzoate ester
  • Benzoic acid or derivatives
  • Benzoyl
  • Monocyclic benzene moiety
  • Benzenoid
  • Dicarboxylic acid or derivatives
  • Tertiary alcohol
  • 1,2-diol
  • Secondary alcohol
  • Carboxylic acid ester
  • Ketone
  • Carboxylic acid derivative
  • Carbonyl group
  • Alcohol
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic 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
logP3.97ALOGPS
logP5.28ChemAxon
logS-5.6ALOGPS
pKa (Strongest Acidic)12.14ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area110.13 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity153.67 m³·mol⁻¹ChemAxon
Polarizability58.4 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
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]