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Record Information
Version2.0
Created at2022-09-06 04:27:03 UTC
Updated at2022-09-06 04:27:03 UTC
NP-MRD IDNP0225662
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1's,2r,2's,4's,7's,8'r,9's,12's,13's,14's,15'r,16'r,18's)-14'-(acetyloxy)-16',18'-dihydroxy-7',9',13'-trimethyl-5-methylidene-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-15'-yl acetate
DescriptionTupichigenin Ac belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. (1's,2r,2's,4's,7's,8'r,9's,12's,13's,14's,15'r,16'r,18's)-14'-(acetyloxy)-16',18'-dihydroxy-7',9',13'-trimethyl-5-methylidene-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-15'-yl acetate is found in Rohdea chinensis. Based on a literature review very few articles have been published on tupichigenin Ac.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC31H46O8
Average Mass546.7010 Da
Monoisotopic Mass546.31927 Da
IUPAC Name(1'S,2R,2'S,4'S,7'S,8'R,9'S,12'S,13'S,14'S,15'R,16'R,18'S)-14'-(acetyloxy)-16',18'-dihydroxy-7',9',13'-trimethyl-5-methylidene-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosane]-15'-yl acetate
Traditional Name(1'S,2R,2'S,4'S,7'S,8'R,9'S,12'S,13'S,14'S,15'R,16'R,18'S)-14'-(acetyloxy)-16',18'-dihydroxy-7',9',13'-trimethyl-5-methylidene-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosane]-15'-yl acetate
CAS Registry NumberNot Available
SMILES
C[C@H]1[C@H]2[C@H](C[C@H]3[C@@H]4CC[C@]5(O)C[C@@H](O)[C@@H](OC(C)=O)[C@@H](OC(C)=O)[C@]5(C)[C@H]4CC[C@]23C)O[C@]11CCC(=C)CO1
InChI Identifier
InChI=1S/C31H46O8/c1-16-7-12-31(36-15-16)17(2)25-24(39-31)13-22-20-8-11-30(35)14-23(34)26(37-18(3)32)27(38-19(4)33)29(30,6)21(20)9-10-28(22,25)5/h17,20-27,34-35H,1,7-15H2,2-6H3/t17-,20+,21-,22-,23+,24-,25-,26+,27+,28-,29-,30-,31+/m0/s1
InChI KeyORRBQAHWWZOTHR-VKFJXMKWSA-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
Rohdea chinensisLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTriterpenoids
Direct ParentTriterpenoids
Alternative Parents
Substituents
  • Triterpenoid
  • Spirostane skeleton
  • Steroid ester
  • 3-hydroxysteroid
  • 5-hydroxysteroid
  • 3-beta-hydroxysteroid
  • Hydroxysteroid
  • Steroid
  • Ketal
  • Cyclitol or derivatives
  • Dicarboxylic acid or derivatives
  • Oxane
  • Cyclic alcohol
  • Tetrahydrofuran
  • Tertiary alcohol
  • Carboxylic acid ester
  • Secondary alcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Carboxylic acid derivative
  • Acetal
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Alcohol
  • 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
logP2.72ChemAxon
pKa (Strongest Acidic)13.78ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area111.52 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity141.47 m³·mol⁻¹ChemAxon
Polarizability61.03 ųChemAxon
Number of Rings6ChemAxon
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 ID9148829
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10973623
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]