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(6beta,22E)-6-Hydroxystigmasta-4,22-dien-3-one (FDB019019)

Record Information
Version1.0
Creation date2010-04-08 22:14:05 UTC
Update date2019-11-26 03:16:59 UTC
Primary IDFDB019019
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(6beta,22E)-6-Hydroxystigmasta-4,22-dien-3-one
DescriptionGraecunin D belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds. Graecunin D is a very strong basic compound (based on its pKa). Graecunin D has been detected, but not quantified in, fenugreeks and herbs and spices. This could make graecunin D a potential biomarker for the consumption of these foods.
CAS Number36450-01-8
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility9.0e-05 g/LALOGPS
logP5.72ALOGPS
logP6.82ChemAxon
logS-6.7ALOGPS
pKa (Strongest Acidic)14.55ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity131.35 m³·mol⁻¹ChemAxon
Polarizability53.04 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC29H46O2
IUPAC name14-[(3E)-5-ethyl-6-methylhept-3-en-2-yl]-8-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one
InChI IdentifierInChI=1S/C29H46O2/c1-7-20(18(2)3)9-8-19(4)23-10-11-24-22-17-27(31)26-16-21(30)12-14-29(26,6)25(22)13-15-28(23,24)5/h8-9,16,18-20,22-25,27,31H,7,10-15,17H2,1-6H3/b9-8+
InChI KeyFFKIQLXJMQUBQZ-CMDGGOBGSA-N
Isomeric SMILESCCC(\C=C\C(C)C1CCC2C3CC(O)C4=CC(=O)CCC4(C)C3CCC12C)C(C)C
Average Molecular Weight426.6743
Monoisotopic Molecular Weight426.349780716
Classification
Description Belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentOligopeptides
Alternative Parents
Substituents
  • Alpha-oligopeptide
  • Tyrosine or derivatives
  • Phenylalanine or derivatives
  • Glutamic acid or derivatives
  • Proline or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Triptan
  • N-substituted-alpha-amino acid
  • Alpha-amino acid or derivatives
  • Amphetamine or derivatives
  • 3-alkylindole
  • Indole
  • Indole or derivatives
  • Tricarboxylic acid or derivatives
  • N-acylpyrrolidine
  • Pyrrolidine carboxylic acid or derivatives
  • Pyrrolidine-2-carboxamide
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Fatty acyl
  • Fatty amide
  • Substituted pyrrole
  • N-acyl-amine
  • Benzenoid
  • Monocyclic benzene moiety
  • Tertiary carboxylic acid amide
  • Heteroaromatic compound
  • Pyrrolidine
  • Pyrrole
  • Amino acid
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Amino acid or derivatives
  • Carboxamide group
  • Carboxylic acid
  • Organoheterocyclic compound
  • Azacycle
  • Organic nitrogen compound
  • Primary amine
  • Organic oxide
  • Primary aliphatic amine
  • Hydrocarbon derivative
  • Alcohol
  • Carbonyl group
  • Organonitrogen compound
  • Organopnictogen compound
  • Organooxygen compound
  • Amine
  • Organic oxygen compound
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 81.63%; H 10.87%; O 7.50%DFC
Melting PointMp 210-212°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D +8 (CHCl3)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS(6beta,22E)-6-Hydroxystigmasta-4,22-dien-3-one, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-01ot-2539400000-1a80f107e98a6dfb1014Spectrum
Predicted GC-MS(6beta,22E)-6-Hydroxystigmasta-4,22-dien-3-one, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0089-3110900000-569d27144f5845d89130Spectrum
Predicted GC-MS(6beta,22E)-6-Hydroxystigmasta-4,22-dien-3-one, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a6r-1003900000-f0d4a526f0799e3970222016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052b-9117300000-1d725a3ac7f327d4d5792016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9244100000-d559557bd57e1b7ae0412016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000900000-831434336808117e35af2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0000900000-eadc086e616e821646fc2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4j-5009600000-191fffb24346565d08502016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000900000-e0002f0b464d749332dc2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0000900000-1f55a150ad52bf9e55c02021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-1006900000-7dca246ceacad3837a562021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0125900000-1d8c135e0ea5a558e6de2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0560-9257300000-9bf0059e52ac0f51f52c2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06si-9632000000-dfa4b9bc283d678376232021-09-25View Spectrum
NMRNot Available
ChemSpider ID21433188
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID95793
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB39425
CRC / DFC (Dictionary of Food Compounds) IDLNP72-V:LNP73-W
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 ReferenceNot Available
Content Reference