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Record Information
Version2.0
Created at2022-09-11 13:13:11 UTC
Updated at2022-09-11 13:13:11 UTC
NP-MRD IDNP0314881
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1's,2r,2's,4's,5s,7's,8'r,9's,12's,13'r,16's)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-18'-ene-5,16'-diol
DescriptionIsonuatigenin belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Thus, isonuatigenin is considered to be a sterol. (1's,2r,2's,4's,5s,7's,8'r,9's,12's,13'r,16's)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-18'-ene-5,16'-diol is found in Solanum myriacanthum, Tacca leontopetaloides and Vestia lycioides. (1's,2r,2's,4's,5s,7's,8'r,9's,12's,13'r,16's)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-18'-ene-5,16'-diol was first documented in 2005 (PMID: 15990250). Based on a literature review very few articles have been published on Isonuatigenin (PMID: 33788045).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC27H42O4
Average Mass430.6290 Da
Monoisotopic Mass430.30831 Da
IUPAC Name(1'S,2R,2'S,4'S,5S,7'S,8'R,9'S,12'S,13'R,16'S)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosan]-18'-ene-5,16'-diol
Traditional Name(1'S,2R,2'S,4'S,5S,7'S,8'R,9'S,12'S,13'R,16'S)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosan]-18'-ene-5,16'-diol
CAS Registry NumberNot Available
SMILES
C[C@H]1[C@H]2[C@H](C[C@H]3[C@@H]4CC=C5C[C@@H](O)CC[C@]5(C)[C@H]4CC[C@]23C)O[C@]11CC[C@](C)(O)CO1
InChI Identifier
InChI=1S/C27H42O4/c1-16-23-22(31-27(16)12-11-24(2,29)15-30-27)14-21-19-6-5-17-13-18(28)7-9-25(17,3)20(19)8-10-26(21,23)4/h5,16,18-23,28-29H,6-15H2,1-4H3/t16-,18-,19+,20-,21-,22-,23-,24-,25-,26-,27+/m0/s1
InChI KeyNHBDEADLHQSGDF-SGKAZYAESA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Solanum myriacanthumLOTUS Database
Tacca leontopetaloidesLOTUS Database
Vestia lycioidesLOTUS 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
  • 3-hydroxy-delta-5-steroid
  • 3-hydroxysteroid
  • Hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • 3-beta-hydroxysteroid
  • Steroid
  • Delta-5-steroid
  • Ketal
  • Oxane
  • Tetrahydrofuran
  • Tertiary alcohol
  • Cyclic alcohol
  • Secondary alcohol
  • Acetal
  • Organoheterocyclic compound
  • Oxacycle
  • Organic oxygen compound
  • Organooxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • 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
logP3.77ChemAxon
pKa (Strongest Acidic)14.27ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area58.92 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity121.79 m³·mol⁻¹ChemAxon
Polarizability51.46 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
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 ID62992466
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound12311129
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Guo J, Zhao J, Liu R, Yu J, Zhang M, Wang H, Liu L: Metabolomics analysis of serum in pediatric nephrotic syndrome based on targeted and non-targeted platforms. Metabolomics. 2021 Mar 31;17(4):38. doi: 10.1007/s11306-021-01788-1. [PubMed:33788045 ]
  2. Ferro EA, Alvarenga NL, Ibarrola DA, Hellion-Ibarrola MC, Ravelo AG: A new steroidal saponin from Solanum sisymbriifolium roots. Fitoterapia. 2005 Sep;76(6):577-9. doi: 10.1016/j.fitote.2005.04.008. [PubMed:15990250 ]
  3. LOTUS database [Link]