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Record Information
Version2.0
Created at2022-09-09 19:56:35 UTC
Updated at2022-09-09 19:56:35 UTC
NP-MRD IDNP0289651
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1's,2r,2's,4's,5r,7's,8'r,9's,12's,13'r,15'r,16'r)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-18'-ene-15',16'-diol
DescriptionYuccagenin belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Thus, yuccagenin is considered to be a sterol. (1's,2r,2's,4's,5r,7's,8'r,9's,12's,13'r,15'r,16'r)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-18'-ene-15',16'-diol is found in Agave lecheguilla, Allium karataviense, Allium rotundum, Allium stipitatum, Trigonella foenum-graecum and Yucca schottii. (1's,2r,2's,4's,5r,7's,8'r,9's,12's,13'r,15'r,16'r)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-18'-ene-15',16'-diol was first documented in 2008 (PMID: 19419073). Based on a literature review very few articles have been published on Yuccagenin.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC27H42O4
Average Mass430.6290 Da
Monoisotopic Mass430.30831 Da
IUPAC Name(1'S,2R,2'S,4'S,5R,7'S,8'R,9'S,12'S,13'R,15'R,16'R)-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-15',16'-diol
Traditional Name(1'S,2R,2'S,4'S,5R,7'S,8'R,9'S,12'S,13'R,15'R,16'R)-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-15',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)[C@H](O)C[C@]5(C)[C@H]4CC[C@]23C)O[C@]11CC[C@@H](C)CO1
InChI Identifier
InChI=1S/C27H42O4/c1-15-7-10-27(30-14-15)16(2)24-23(31-27)12-20-18-6-5-17-11-21(28)22(29)13-26(17,4)19(18)8-9-25(20,24)3/h5,15-16,18-24,28-29H,6-14H2,1-4H3/t15-,16+,18-,19+,20+,21-,22-,23+,24+,25+,26+,27-/m1/s1
InChI KeyORXKASWXOVPKDV-UBWBUNFISA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Agave lechuguillaLOTUS Database
Allium karatavienseLOTUS Database
Allium rotundumLOTUS Database
Allium stipitatumLOTUS Database
Trigonella foenum-graecumLOTUS Database
Yucca schottiiLOTUS 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
  • 2-hydroxysteroid
  • 3-beta-hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • Hydroxysteroid
  • Delta-5-steroid
  • Steroid
  • Ketal
  • Oxane
  • Cyclic alcohol
  • Tetrahydrofuran
  • 1,2-diol
  • Secondary alcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Acetal
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
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
logP3.85ChemAxon
pKa (Strongest Acidic)13.85ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area58.92 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity121.63 m³·mol⁻¹ChemAxon
Polarizability51.63 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 ID2340787
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound3083608
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Guerra JO, Meneses A, Simonet AM, Macias FA, Nogueiras C, Gomez A, Escario JA: [Steroidal saponins from the plant Agave brittoniana with activity against the parasite Trichomona vaginalis]. Rev Biol Trop. 2008 Dec;56(4):1645-52. [PubMed:19419073 ]
  2. LOTUS database [Link]