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Record Information
Version2.0
Created at2022-09-10 02:02:31 UTC
Updated at2022-09-10 02:02:32 UTC
NP-MRD IDNP0293819
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1's,3r,3'r,3as,7r,7'r,8as,9's,10's)-12'-acetyl-10'-hydroxy-7,9'-dimethyl-4'-methylidene-6-(3-oxobutyl)-4,7,8,8a-tetrahydro-3ah-6'-oxaspiro[cyclohepta[b]furan-3,13'-tricyclo[8.4.0.0³,⁷]tetradecan]-11'-ene-2,5'-dione
Description(1'S,3R,3'R,3aS,7R,7'R,8aS,9'S,10'S)-12'-acetyl-10'-hydroxy-7,9'-dimethyl-4'-methylidene-6-(3-oxobutyl)-2,3a,4,7,8,8a-hexahydro-6'-oxaspiro[cyclohepta[b]furan-3,13'-tricyclo[8.4.0.0³,⁷]Tetradecan]-11'-ene-2,5'-dione belongs to the class of organic compounds known as xanthanolides. These are sesquiterpenoids with a structure based on the xanthanolide skeleton consistsing of a cycloheptane ring usually attached to a four-carbon chain (at carbon 1 ) and a methyl group (at carbon 10), and fused to a five-member lactone ring (sharing carbons 7 and 8). The lactone ring can be conjugated with a methyl or methylene group at position 11. (1's,3r,3'r,3as,7r,7'r,8as,9's,10's)-12'-acetyl-10'-hydroxy-7,9'-dimethyl-4'-methylidene-6-(3-oxobutyl)-4,7,8,8a-tetrahydro-3ah-6'-oxaspiro[cyclohepta[b]furan-3,13'-tricyclo[8.4.0.0³,⁷]tetradecan]-11'-ene-2,5'-dione is found in Xanthium strumarium. Based on a literature review very few articles have been published on (1'S,3R,3'R,3aS,7R,7'R,8aS,9'S,10'S)-12'-acetyl-10'-hydroxy-7,9'-dimethyl-4'-methylidene-6-(3-oxobutyl)-2,3a,4,7,8,8a-hexahydro-6'-oxaspiro[cyclohepta[b]furan-3,13'-tricyclo[8.4.0.0³,⁷]Tetradecan]-11'-ene-2,5'-dione.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC30H38O7
Average Mass510.6270 Da
Monoisotopic Mass510.26175 Da
IUPAC Name(1'S,3R,3'R,3aS,7R,7'R,8aS,9'S,10'S)-12'-acetyl-10'-hydroxy-7,9'-dimethyl-4'-methylidene-6-(3-oxobutyl)-2,3a,4,7,8,8a-hexahydro-6'-oxaspiro[cyclohepta[b]furan-3,13'-tricyclo[8.4.0.0^{3,7}]tetradecan]-11'-ene-2,5'-dione
Traditional Name(1'S,3R,3'R,3aS,7R,7'R,8aS,9'S,10'S)-12'-acetyl-10'-hydroxy-7,9'-dimethyl-4'-methylidene-6-(3-oxobutyl)-4,7,8,8a-tetrahydro-3aH-6'-oxaspiro[cyclohepta[b]furan-3,13'-tricyclo[8.4.0.0^{3,7}]tetradecan]-11'-ene-2,5'-dione
CAS Registry NumberNot Available
SMILES
C[C@@H]1C[C@@H]2OC(=O)[C@]3(C[C@@H]4C[C@H]5[C@@H](C[C@H](C)[C@@]4(O)C=C3C(C)=O)OC(=O)C5=C)[C@@H]2CC=C1CCC(C)=O
InChI Identifier
InChI=1S/C30H38O7/c1-15-10-26-23(9-8-20(15)7-6-17(3)31)29(28(34)37-26)13-21-12-22-18(4)27(33)36-25(22)11-16(2)30(21,35)14-24(29)19(5)32/h8,14-16,21-23,25-26,35H,4,6-7,9-13H2,1-3,5H3/t15-,16+,21+,22-,23-,25-,26+,29-,30+/m1/s1
InChI KeyWJIPAPYZRBJZDU-PNHQVPILSA-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
Xanthium strumariumLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as xanthanolides. These are sesquiterpenoids with a structure based on the xanthanolide skeleton consistsing of a cycloheptane ring usually attached to a four-carbon chain (at carbon 1 ) and a methyl group (at carbon 10), and fused to a five-member lactone ring (sharing carbons 7 and 8). The lactone ring can be conjugated with a methyl or methylene group at position 11.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene lactones
Direct ParentXanthanolides
Alternative Parents
Substituents
  • Xanthanolide-skeleton
  • Sesquiterpenoid
  • Dicarboxylic acid or derivatives
  • Gamma butyrolactone
  • Cyclic alcohol
  • Tertiary alcohol
  • Tetrahydrofuran
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Lactone
  • Ketone
  • Carboxylic acid ester
  • Oxacycle
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Carbonyl group
  • 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
logP3.5ChemAxon
pKa (Strongest Acidic)13.91ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area106.97 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity137.55 m³·mol⁻¹ChemAxon
Polarizability55.35 ųChemAxon
Number of Rings5ChemAxon
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 Compound95224227
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]