hederagenin (PAMDB110357)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB110357
Identification
Name: hederagenin
Description:A sapogenin that is olean-12-en-28-oic acid substituted by hydroxy groups at positions 3 and 23 (the 3β stereoisomer).
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • Caulosapogenin
  • Astrantiagenin E
  • Hederagenic acid
  • (3-beta,4-alpha)-3,23-Dihydroxyolean-12-en-28-oic acid
Chemical Formula: C30H47O4
Average Molecular Weight: 471.7
Monoisotopic Molecular Weight: 472.3552600292
InChI Key: PGOYMURMZNDHNS-AFDXFISUSA-M
InChI: 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)/p-1/t20?,21?,22?,23-,26-,27+,28+,29+,30-/m0/s1
CAS number: Not Available
IUPAC Name:(3β)-3,23-dihydroxyolean-12-en-28-oic acid
Traditional IUPAC Name: Not Available
SMILES:CC5(CCC4(CCC1(C(=CCC2(C1(CCC3(C2(CCC(C3(C)CO)O)C))C))C4C5)C)C(=O)[O-])C
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.
Kingdom Organic compounds
Super ClassLipids and lipid-like molecules
Class Prenol lipids
Sub ClassTriterpenoids
Direct Parent Triterpenoids
Alternative Parents Not Available
Substituents
  • Triterpenoid
  • Steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Carbonyl group
  • Primary alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organic anion
  • Aliphatic homopolycyclic compound
Molecular Framework Aliphatic homopolycyclic compounds
External Descriptors
  • a triterpenoid (CPD-9481)
Physical Properties
State: Not Available
Charge:0
Melting point: Not Available
Experimental Properties: Not Available
Predicted Properties
PropertyValueSource
3D Conformer25201740 PubChem
Molecular Weight471.702 g/molPubChem
XLogP3-AA7.5 PubChem
Hydrogen Bond Donor Count2 PubChem
Hydrogen Bond Acceptor Count4 PubChem
Rotatable Bond Count1 PubChem
Exact Mass471.347 g/molPubChem
Monoisotopic Mass471.347 g/molPubChem
Topological Polar Surface Area80.6 A^2PubChem
Heavy Atom Count34 PubChem
Formal Charge-1 PubChem
Complexity902 PubChem
Isotope Atom Count0 PubChem
Defined Atom Stereocenter Count6 PubChem
Undefined Atom Stereocenter Count3 PubChem
Defined Bond Stereocenter Count0 PubChem
Undefined Bond Stereocenter Count0 PubChem
Covalently-Bonded Unit Count1 PubChem
Biological Properties
Cellular Locations: Not Available
Reactions:
Pathways:
    Spectra
    Spectra: Not Available
    References
    References:
    • Jin ZL, Gao N, Zhou D, Chi MG, Yang XM, Xu JP (2012)The extracts of Fructus Akebiae, a preparation containing 90% of the active ingredient hederagenin: serotonin, norepinephrine and dopamine reuptake inhibitor. Pharmacology, biochemistry, and behavior 100, Pubmed: 22005599
    • Lorent J, Le Duff CS, Quetin-Leclercq J, Mingeot-Leclercq MP (2013)Induction of highly curved structures in relation to membrane permeabilization and budding by the triterpenoid saponins, a- and d-Hederin. The Journal of biological chemistry 288, Pubmed: 23530040
    Synthesis Reference: Not Available
    Material Safety Data Sheet (MSDS) Not Available
    External Links:
    ResourceLink
    ChEBI69579
    MetaboLightsMTBLC69579
    PubChem25201740