Np mrd loader

Record Information
Version2.0
Created at2022-09-10 02:02:05 UTC
Updated at2022-09-10 02:02:05 UTC
NP-MRD IDNP0293814
Secondary Accession NumbersNone
Natural Product Identification
Common Namemethyl 3-{[(2e)-3,4-dimethylpent-2-enoyl]oxy}-15,16-dihydroxy-9,13-dimethyl-4,12-dioxo-11-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-10-ene-17-carboxylate
DescriptionMethyl 3-[(E)-3,4-dimethylpent-2-enoyl]oxy-15,16-dihydroxy-9,13-dimethyl-4,12-dioxo-11-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]Nonadec-10-ene-17-carboxylate, also known as 3-0-(glucopyranosyl)bruceantin or bruceantinoside b, 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. methyl 3-{[(2e)-3,4-dimethylpent-2-enoyl]oxy}-15,16-dihydroxy-9,13-dimethyl-4,12-dioxo-11-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-10-ene-17-carboxylate is found in Brucea antidysenterica and Brucea javanica. Based on a literature review very few articles have been published on Methyl 3-[(E)-3,4-dimethylpent-2-enoyl]oxy-15,16-dihydroxy-9,13-dimethyl-4,12-dioxo-11-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]Nonadec-10-ene-17-carboxylate.
Structure
Thumb
Synonyms
ValueSource
Methyl 3-[(e)-3,4-dimethylpent-2-enoyl]oxy-15,16-dihydroxy-9,13-dimethyl-4,12-dioxo-11-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-10-ene-17-carboxylic acidGenerator
3-0-(Glucopyranosyl)bruceantinMeSH
Bruceantinoside bMeSH
Yadanzioside pMeSH
Chemical FormulaC34H46O16
Average Mass710.7260 Da
Monoisotopic Mass710.27859 Da
IUPAC Namemethyl 3-{[(2E)-3,4-dimethylpent-2-enoyl]oxy}-15,16-dihydroxy-9,13-dimethyl-4,12-dioxo-11-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,18-dioxapentacyclo[12.5.0.0^{1,6}.0^{2,17}.0^{8,13}]nonadec-10-ene-17-carboxylate
Traditional Namemethyl 3-{[(2E)-3,4-dimethylpent-2-enoyl]oxy}-15,16-dihydroxy-9,13-dimethyl-4,12-dioxo-11-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,18-dioxapentacyclo[12.5.0.0^{1,6}.0^{2,17}.0^{8,13}]nonadec-10-ene-17-carboxylate
CAS Registry NumberNot Available
SMILES
COC(=O)C12OCC34C1C(OC(=O)\C=C(/C)C(C)C)C(=O)OC3CC1C(C)C=C(OC3OC(CO)C(O)C(O)C3O)C(=O)C1(C)C4C(O)C2O
InChI Identifier
InChI=1S/C34H46O16/c1-12(2)13(3)8-19(36)50-24-26-33-11-46-34(26,31(44)45-6)28(42)23(40)25(33)32(5)15(9-18(33)49-29(24)43)14(4)7-16(27(32)41)47-30-22(39)21(38)20(37)17(10-35)48-30/h7-8,12,14-15,17-18,20-26,28,30,35,37-40,42H,9-11H2,1-6H3/b13-8+
InChI KeyYSFALLIAQRJCQF-MDWZMJQESA-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
Brucea antidysentericaLOTUS Database
Brucea javanicaLOTUS 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
  • C-20 quassinoid skeleton
  • Quassinoid
  • Fatty acyl glycoside of mono- or disaccharide
  • Fatty acyl glycoside
  • Naphthopyran
  • Hexose monosaccharide
  • O-glycosyl compound
  • Glycosyl compound
  • Naphthalene
  • Tricarboxylic acid or derivatives
  • Furopyran
  • Cyclohexenone
  • Oxepane
  • Delta_valerolactone
  • Fatty acid ester
  • Delta valerolactone
  • Beta-hydroxy acid
  • Fatty acyl
  • Pyran
  • Oxane
  • Monosaccharide
  • Hydroxy acid
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Methyl ester
  • Tetrahydrofuran
  • Furan
  • Cyclic alcohol
  • Secondary alcohol
  • Lactone
  • Ketone
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Ether
  • Dialkyl ether
  • Carboxylic acid derivative
  • Acetal
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • 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
logP-0.78ChemAxon
pKa (Strongest Acidic)12.09ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area245.04 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity166.8 m³·mol⁻¹ChemAxon
Polarizability70.86 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 ID4940880
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6436230
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]