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Record Information
Version2.0
Created at2022-09-09 23:53:28 UTC
Updated at2022-09-09 23:53:29 UTC
NP-MRD IDNP0292383
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1r,2s,3r,6r,8s,12s,13s,14r,15r,16s)-12,15,16-trihydroxy-9,13,17-trimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-en-3-yl 2-methylbutanoate
Description(1R,2S,3R,6R,8S,12S,13S,14R,15R,16S)-12,15,16-trihydroxy-9,13,17-trimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]Nonadec-9-en-3-yl 2-methylbutanoate belongs to the class of organic compounds known as quassinoids. These are a group of compounds chemically degraded from triterpenes. According to their basic skeleton, quassinoids are categorized into five distinct groups, C-18, C-19, C-20, C-22 and C-25 types. The C-20 quassinoids can be further classified into two types, tetracyclic and the pentacyclic. The tetracyclic variety does not have oxygenation at C-20, while the pentacyclic quassinoids possess additional oxygenation at C-20 that allows for the formation of an additional ring. (1r,2s,3r,6r,8s,12s,13s,14r,15r,16s)-12,15,16-trihydroxy-9,13,17-trimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-en-3-yl 2-methylbutanoate is found in Leitneria floridana, Quassia africana, Quassia amara, Simaba guianensis and Simaba orinocensis. Based on a literature review very few articles have been published on (1R,2S,3R,6R,8S,12S,13S,14R,15R,16S)-12,15,16-trihydroxy-9,13,17-trimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]Nonadec-9-en-3-yl 2-methylbutanoate.
Structure
Thumb
Synonyms
ValueSource
(1R,2S,3R,6R,8S,12S,13S,14R,15R,16S)-12,15,16-Trihydroxy-9,13,17-trimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0,.0,.0,]nonadec-9-en-3-yl 2-methylbutanoic acidGenerator
Chemical FormulaC25H34O9
Average Mass478.5380 Da
Monoisotopic Mass478.22028 Da
IUPAC Name(1R,2S,3R,6R,8S,12S,13S,14R,15R,16S)-12,15,16-trihydroxy-9,13,17-trimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0^{1,6}.0^{2,17}.0^{8,13}]nonadec-9-en-3-yl 2-methylbutanoate
Traditional Name(1R,2S,3R,6R,8S,12S,13S,14R,15R,16S)-12,15,16-trihydroxy-9,13,17-trimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0^{1,6}.0^{2,17}.0^{8,13}]nonadec-9-en-3-yl 2-methylbutanoate
CAS Registry NumberNot Available
SMILES
CCC(C)C(=O)O[C@@H]1[C@H]2C3(C)OC[C@]22[C@@H](C[C@H]4C(C)=CC(=O)[C@@H](O)[C@]4(C)[C@H]2[C@@H](O)[C@@H]3O)OC1=O
InChI Identifier
InChI=1S/C25H34O9/c1-6-10(2)21(30)34-16-18-24(5)20(29)15(27)17-23(4)12(11(3)7-13(26)19(23)28)8-14(33-22(16)31)25(17,18)9-32-24/h7,10,12,14-20,27-29H,6,8-9H2,1-5H3/t10?,12-,14+,15+,16+,17+,18-,19+,20-,23-,24?,25+/m0/s1
InChI KeyOKIKYYZNNZCZRX-CWFVKNSDSA-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
Leitneria floridanaLOTUS Database
Quassia africanaLOTUS Database
Quassia amaraLOTUS Database
Simaba guianensisLOTUS Database
Simaba orinocensisLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as quassinoids. These are a group of compounds chemically degraded from triterpenes. According to their basic skeleton, quassinoids are categorized into five distinct groups, C-18, C-19, C-20, C-22 and C-25 types. The C-20 quassinoids can be further classified into two types, tetracyclic and the pentacyclic. The tetracyclic variety does not have oxygenation at C-20, while the pentacyclic quassinoids possess additional oxygenation at C-20 that allows for the formation of an additional ring.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene lactones
Direct ParentQuassinoids
Alternative Parents
Substituents
  • Polycyclic triterpenoid
  • Triterpenoid
  • C-20 quassinoid skeleton
  • Quassinoid
  • Naphthopyran
  • Naphthalene
  • Furopyran
  • Delta_valerolactone
  • Cyclohexenone
  • Delta valerolactone
  • Fatty acid ester
  • Oxepane
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • Oxane
  • Pyran
  • Furan
  • Cyclic alcohol
  • Tetrahydrofuran
  • Cyclic ketone
  • Lactone
  • Carboxylic acid ester
  • Ketone
  • Secondary alcohol
  • Carboxylic acid derivative
  • Dialkyl ether
  • Oxacycle
  • Ether
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Carbonyl group
  • Alcohol
  • Organic oxygen compound
  • Organic oxide
  • Organooxygen compound
  • 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
logP0.54ChemAxon
pKa (Strongest Acidic)12.66ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area139.59 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity117.23 m³·mol⁻¹ChemAxon
Polarizability48.78 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 ID283418
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound320171
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]