Record Information
Version1.0
Creation date2010-04-08 22:07:18 UTC
Update date2018-05-28 23:15:29 UTC
Primary IDFDB006785
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameFriedelin
DescriptionFriedelin is a member of the class of compounds known as triterpenoids. Triterpenoids are terpene molecules containing six isoprene units. Friedelin is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Friedelin can be found in a number of food items such as pomegranate, sugar apple, apple, and mammee apple, which makes friedelin a potential biomarker for the consumption of these food products. Friedelin is a triterpenoid chemical compound found in Azima tetracantha, Orostachys japonica, and Quercus stenophylla. Friedelin is also found in the roots of the Cannabis plant .
CAS Number559-74-0
Structure
Thumb
Synonyms
SynonymSource
(-)-friedelinbiospider
D:A-Friedooleanan-3-onebiospider
D:A-Friedooleanan-3-one (VAN)biospider
Friedelan-3-onebiospider
Friedelinbiospider
Friedelinebiospider
Friedleinbiospider
Predicted Properties
PropertyValueSource
Water Solubility3.0e-05 g/LALOGPS
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
Polarizability53.67 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC30H50O
IUPAC name4,4a,6b,8a,11,11,12b,14a-octamethyl-docosahydropicen-3-one
InChI IdentifierInChI=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
InChI KeyOFMXGFHWLZPCFL-UHFFFAOYSA-N
Isomeric SMILESCC1C(=O)CCC2C1(C)CCC1C2(C)CCC2(C)C3CC(C)(C)CCC3(C)CCC12C
Average Molecular Weight426.7174
Monoisotopic Molecular Weight426.386166222
Classification
DescriptionThis compound belongs to the class of organic compounds known as taraxerane, multiflorane, glutinane and friedelane triterpenoids. These are triterpenoids with a structure based either on the taraxerane, the multiflorane, the glutinane, or the friedelane skeleton. These compounds arise upon rearrangement of the oleanane skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTriterpenoids
Direct ParentTaraxerane, multiflorane, glutinane and friedelane triterpenoids
Alternative Parents
Substituents
  • Taraxerane, multiflorane, glutinane and friedelane triterpenoid
  • Cyclohexanone
  • Cyclic ketone
  • Ketone
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting Point263 oC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0001900000-3ccfe4ea99fee2319b92View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05xr-1139500000-ad43ad3ede8c9aefb585View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0301-0129200000-9c7626288497687e9383View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000900000-85121ee7de310becbfe2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0000900000-33763ebbf1acb6ffc650View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-4009500000-fefc8ccf722c110a0010View in MoNA
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC08626
Pubchem Compound ID244297
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDFRIEDELIN
BIGG IDNot Available
KNApSAcK IDC00003747
HET IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
diuretic35498 An agent that promotes the excretion of urine through its effects on kidney function.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).