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Record Information
Version2.0
Created at2022-09-06 22:26:30 UTC
Updated at2022-09-06 22:26:31 UTC
NP-MRD IDNP0238956
Secondary Accession NumbersNone
Natural Product Identification
Common Name4-epihederagenin
Description4-Epihederagenin belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. 4-epihederagenin is found in Lantana indica, Rubia yunnanensis and Scutellaria strigillosa. 4-epihederagenin was first documented in 2010 (PMID: 20387830). Based on a literature review very few articles have been published on 4-epihederagenin.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC30H48O4
Average Mass472.7100 Da
Monoisotopic Mass472.35526 Da
IUPAC Name(4aS,6aS,6bR,8aR,9S,10S,12aR,12bR,14bS)-10-hydroxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid
Traditional Name(4aS,6aS,6bR,8aR,9S,10S,12aR,12bR,14bS)-10-hydroxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid
CAS Registry NumberNot Available
SMILES
CC1(C)CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@H](O)[C@](C)(CO)[C@@H]5CC[C@@]34C)[C@@H]2C1)C(O)=O
InChI Identifier
InChI=1S/C30H48O4/c1-25(2)13-15-30(24(33)34)16-14-28(5)19(20(30)17-25)7-8-22-26(3)11-10-23(32)27(4,18-31)21(26)9-12-29(22,28)6/h7,20-23,31-32H,8-18H2,1-6H3,(H,33,34)/t20-,21+,22+,23-,26-,27+,28+,29+,30-/m0/s1
InChI KeyPGOYMURMZNDHNS-YGUUOLNVSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Lantana indicaLOTUS Database
Rubia yunnanensisLOTUS Database
Scutellaria strigillosaLOTUS 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
  • Steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic 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
logP5.31ChemAxon
pKa (Strongest Acidic)4.74ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity135.4 m³·mol⁻¹ChemAxon
Polarizability55.98 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 ID10217377
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound12302577
PDB IDNot Available
ChEBI ID69528
Good Scents IDNot Available
References
General References
  1. Nielsen NJ, Nielsen J, Staerk D: New resistance-correlated saponins from the insect-resistant crucifer Barbarea vulgaris. J Agric Food Chem. 2010 May 12;58(9):5509-14. doi: 10.1021/jf903988f. [PubMed:20387830 ]
  2. LOTUS database [Link]