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Schottenol 3-ferulate (FDB000312)

Record Information
Version1.0
Creation date2010-04-08 22:04:31 UTC
Update date2019-11-26 02:54:37 UTC
Primary IDFDB000312
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameSchottenol 3-ferulate
DescriptionSchottenol 3-ferulate is a member of the class of compounds known as triterpenoids. Triterpenoids are terpene molecules containing six isoprene units. Schottenol 3-ferulate is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Schottenol 3-ferulate can be found in corn, which makes schottenol 3-ferulate a potential biomarker for the consumption of this food product.
CAS Number521-03-9
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility8.3e-06 g/LALOGPS
logP9.18ALOGPS
logP10.42ChemAxon
logS-7.8ALOGPS
pKa (Strongest Acidic)9.87ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area55.76 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity177.78 m³·mol⁻¹ChemAxon
Polarizability73.41 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC39H58O4
IUPAC name(2S,5S,7S,14R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-9-en-5-yl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
InChI IdentifierInChI=1S/C39H58O4/c1-8-28(25(2)3)12-9-26(4)32-15-16-33-31-14-13-29-24-30(19-21-38(29,5)34(31)20-22-39(32,33)6)43-37(41)18-11-27-10-17-35(40)36(23-27)42-7/h10-11,14,17-18,23,25-26,28-30,32-34,40H,8-9,12-13,15-16,19-22,24H2,1-7H3/b18-11+/t26-,28-,29+,30+,32-,33?,34?,38+,39-/m1/s1
InChI KeyBGOCOVGWMXAQCQ-ODEGBJFNSA-N
Isomeric SMILESCC[C@H](CC[C@@H](C)[C@H]1CCC2C3=CC[C@@]4([H])C[C@H](CC[C@]4(C)C3CC[C@]12C)OC(=O)\C=C\C1=CC(OC)=C(O)C=C1)C(C)C
Average Molecular Weight590.8754
Monoisotopic Molecular Weight590.433510344
Classification
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 ester
  • Delta-7-steroid
  • Steroid
  • Cinnamic acid or derivatives
  • Coumaric acid or derivatives
  • Hydroxycinnamic acid or derivatives
  • Cinnamic acid ester
  • Methoxyphenol
  • Anisole
  • Phenoxy compound
  • Phenol ether
  • Methoxybenzene
  • Styrene
  • Phenol
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Monocyclic benzene moiety
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Carboxylic acid ester
  • Ether
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
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
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002f-0503390000-97cb397daf2780992d4e2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002b-4904320000-23cc46596276146943692016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-005j-6449210000-c960c63de033ceb892092016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0201390000-e7a316353682cd6961152016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03dr-0701940000-7be8c6a1bcbfcc0fc70f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03dj-2709610000-94d5f02d237ad46732742016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-02tc-0103390000-8c757bd7131a58afd6d62021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0301-2314490000-8ecb3f0af1f9a77967a22021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052b-7935110000-7c0ff3e07872c491247a2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000090000-d0239152e0913bc74f1e2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900140000-f2e607bd8e5ea1768e282021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001s-0900110000-4fbb0c3b4ba9b3f6c9bc2021-10-21View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID568
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH 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 / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General Reference
  1. Iwatsuki K, Akihisa T, Tokuda H, Ukiya M, Higashihara H, Mukainaka T, Iizuka M, Hayashi Y, Kimura Y, Nishino H: Sterol ferulates, sterols, and 5-alk(en)ylresorcinols from wheat, rye, and corn bran oils and their inhibitory effects on Epstein-Barr virus activation. J Agric Food Chem. 2003 Nov 5;51(23):6683-8. Pubmed [Structure]
Content Reference— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.