Showing Compound Card for Friedelin (CDB000100)

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Record Information
Version1.0
Created at2020-03-18 23:24:46 UTC
Updated at2020-11-18 16:34:46 UTC
CannabisDB IDCDB000100
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameFriedelin
DescriptionFriedelin or Friedooleanan-3-one belongs to the class of organic compounds known as triterpenoids. Triterpenoids are terpene molecules that contain 30 carbon atoms and are comprised of six isoprene units. Triterpenes are the most diverse class of secondary metabolites and can be found in all living organisms. The biosynthesis of triterpenes occurs through the mevalonic acid pathway (MVA; PMID: 17467679 ), mainly in the cytosol. A key intermediate in the biosynthesis of triterpenoids is 2,3-oxidosqualene, which undergoes several cyclization reactions to yield pentacyclic triterpenoids such as friedelin. Friedelin is a neutral compound that is barely soluble in water. It is found in pear and in the leaves of guazuma ulmifolia and apple custard. Friedelin is also found in the roots of the Cannabis plants (PMID: 28826544 ) and in chicory, apple heartwood, pomegranate stem bark and corn stalk ( Ref:DOI ). Friedelin, isolated from the leaves of Azima tetracantha Lam, exhibited anti-ulcer potential in an ethanol-induced gastric ulcer model (PMID: 25617794 ). Seven compounds, including friedelin, were isolated from crude extracts of leaves, stems and roots of Alchornea cordifolia (Schumach. and Thonn.) Müll. Arg. All compounds had antibacterial activity against pathogens of the gastrointestinal, skin, respiratory and urinary tract (PMID: 26724423 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC30H50O
Average Molecular Weight426.73
Monoisotopic Molecular Weight426.3862
IUPAC Name(4S,4aR,6aS,6bS,8aS,12aS,12bS,14aS,14bS)-4,4a,6b,8a,11,11,12b,14a-octamethyl-docosahydropicen-3-one
Traditional Name(4S,4aR,6aS,6bS,8aS,12aS,12bS,14aS,14bS)-4,4a,6b,8a,11,11,12b,14a-octamethyl-tetradecahydro-1H-picen-3-one
CAS Registry Number559-74-0
SMILES
C[C@@H]1C(=O)CC[C@@H]2[C@@]1(C)CC[C@H]1[C@@]2(C)CC[C@@]2(C)[C@H]3CC(C)(C)CC[C@@]3(C)CC[C@@]12C
InChI Identifier
InChI=1S/C30H50O/c1-20-21(31)9-10-22-27(20,5)12-11-23-28(22,6)16-18-30(8)24-19-25(2,3)13-14-26(24,4)15-17-29(23,30)7/h20,22-24H,9-19H2,1-8H3/t20-,22-,23+,24+,26+,27+,28+,29+,30+/m1/s1
InChI KeyOFMXGFHWLZPCFL-VVWBYUDUSA-N
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
  • Cyclic ketone
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Not Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP6.66ALOGPS
logP8.12ChemAxon
logS-7.2ALOGPS
pKa (Strongest Basic)-7.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity130.21 m³·mol⁻¹ChemAxon
Polarizability53.38 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSFriedelin, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSFriedelin, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available2020-06-30View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Russo EB, Marcu J: Cannabis Pharmacology: The Usual Suspects and a Few Promising Leads. Adv Pharmacol. 2017;80:67-134. doi: 10.1016/bs.apha.2017.03.004. Epub 2017 Jun 5. [PubMed:28826544 ]
  2. Buhaescu I, Izzedine H: Mevalonate pathway: a review of clinical and therapeutical implications. Clin Biochem. 2007 Jun;40(9-10):575-84. doi: 10.1016/j.clinbiochem.2007.03.016. Epub 2007 Mar 31. [PubMed:17467679 ]
  3. Antonisamy P, Duraipandiyan V, Aravinthan A, Al-Dhabi NA, Ignacimuthu S, Choi KC, Kim JH: Protective effects of friedelin isolated from Azima tetracantha Lam. against ethanol-induced gastric ulcer in rats and possible underlying mechanisms. Eur J Pharmacol. 2015 Mar 5;750:167-75. doi: 10.1016/j.ejphar.2015.01.015. Epub 2015 Jan 22. [PubMed:25617794 ]
  4. Noundou XS, Krause RW, van Vuuren SF, Ndinteh DT, Olivier DK: Antibacterial effects of Alchornea cordifolia (Schumach. and Thonn.) Mull. Arg extracts and compounds on gastrointestinal, skin, respiratory and urinary tract pathogens. J Ethnopharmacol. 2016 Feb 17;179:76-82. doi: 10.1016/j.jep.2015.12.043. Epub 2015 Dec 24. [PubMed:26724423 ]