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Showing Compound 24-Acetyl- 25-cinnamoylvulgaroside (FDB021293)

Record Information
Version1.0
Creation date2010-04-08 22:15:36 UTC
Update date2019-11-26 03:20:10 UTC
Primary IDFDB021293
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name24-Acetyl- 25-cinnamoylvulgaroside
Description24-Acetyl- 25-cinnamoylvulgaroside belongs to the class of organic compounds known as cheilanthane sesterterpenoids. These are sesterterpnoids with a structure based on the cheilanthane backbone. Cheilanthane is a tricyclic compound consisting of a tetradecahydrophenanthrene ring system that carries two methyl groups at the 1-position, one methyl group at the 4a-,7-, and 8a-positions, as well as a 3-methylpentyl group at the 8-position. Based on a literature review a small amount of articles have been published on 24-Acetyl- 25-cinnamoylvulgaroside.
CAS Number172616-89-6
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
3-(2-{2-[(acetyloxy)methyl]-2-hydroxy-4b,8,8,10a-tetramethyl-tetradecahydrophenanthren-1-yl}-1-hydroxyethyl)-5-oxo-2,5-dihydrofuran-2-yl (2E)-3-phenylprop-2-enoic acidHMDB
Predicted Properties
PropertyValueSource
Water Solubility0.00048 g/LALOGPS
logP4.93ALOGPS
logP6.26ChemAxon
logS-6.1ALOGPS
pKa (Strongest Acidic)1.89ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area119.36 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity165.89 m³·mol⁻¹ChemAxon
Polarizability67.16 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC36H48O8
IUPAC name3-(2-{2-[(acetyloxy)methyl]-2-hydroxy-4b,8,8,10a-tetramethyl-tetradecahydrophenanthren-1-yl}-1-hydroxyethyl)-5-oxo-2,5-dihydrofuran-2-yl (2E)-3-phenylprop-2-enoate
InChI IdentifierInChI=1S/C36H48O8/c1-23(37)42-22-36(41)19-15-28-34(4)17-9-16-33(2,3)27(34)14-18-35(28,5)29(36)21-26(38)25-20-31(40)44-32(25)43-30(39)13-12-24-10-7-6-8-11-24/h6-8,10-13,20,26-29,32,38,41H,9,14-19,21-22H2,1-5H3/b13-12+
InChI KeyIMXZIJOCFAKDPZ-OUKQBFOZSA-N
Isomeric SMILESCC(=O)OCC1(O)CCC2C(C)(CCC3C(C)(C)CCCC23C)C1CC(O)C1=CC(=O)OC1OC(=O)\C=C\C1=CC=CC=C1
Average Molecular Weight608.7615
Monoisotopic Molecular Weight608.334918512
Classification
Description Belongs to the class of organic compounds known as cheilanthane sesterterpenoids. These are sesterterpnoids with a structure based on the cheilanthane backbone. Cheilanthane is a tricyclic compound consisting of a tetradecahydrophenanthrene ring system that carries two methyl groups at the 1-position, one methyl group at the 4a-,7-, and 8a-positions, as well as a 3-methylpentyl group at the 8-position.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesterterpenoids
Direct ParentCheilanthane sesterterpenoids
Alternative Parents
Substituents
  • Cheilanthane sesterterpenoid
  • 13-hydroxysteroid
  • Hydroxysteroid
  • 16-hydroxysteroid
  • Steroid
  • Hydrophenanthrene
  • Phenanthrene
  • Cinnamic acid or derivatives
  • Cinnamic acid ester
  • Tricarboxylic acid or derivatives
  • Styrene
  • Acylal
  • Fatty acid ester
  • Benzenoid
  • Fatty acyl
  • Monocyclic benzene moiety
  • 2-furanone
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Tertiary alcohol
  • Cyclic alcohol
  • Dihydrofuran
  • Secondary alcohol
  • Lactone
  • Carboxylic acid ester
  • Organoheterocyclic compound
  • Oxacycle
  • Carboxylic acid derivative
  • Acetal
  • Carbonyl group
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Organic oxide
  • 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
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 71.03%; H 7.95%; O 21.03%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]25D +17 (c, 1 in CHCl3)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS24-Acetyl- 25-cinnamoylvulgaroside, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001u-2633190000-9d6d5ca2aa4672f3bd2dSpectrum
Predicted GC-MS24-Acetyl- 25-cinnamoylvulgaroside, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00lr-4820239000-43c870bf8ffab89fca64Spectrum
Predicted GC-MS24-Acetyl- 25-cinnamoylvulgaroside, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS24-Acetyl- 25-cinnamoylvulgaroside, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS24-Acetyl- 25-cinnamoylvulgaroside, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS24-Acetyl- 25-cinnamoylvulgaroside, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS24-Acetyl- 25-cinnamoylvulgaroside, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS24-Acetyl- 25-cinnamoylvulgaroside, "24-Acetyl- 25-cinnamoylvulgaroside,1TMS,#1" TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001l-1601392000-ed849e7889dae11750d92017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-1911330000-7361063af552ec79a14b2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uec-4922520000-43c164d0158c6aa954122017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-3900122000-a899209a228552cc85c22017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-9521600000-7b7188d8bc02ccaca69a2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-9800400000-450cbfef1a933e686a5a2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0610589000-81937a8764769d8bebc82021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ue9-1900010000-d2d8b15a6449ae7d322c2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-1901010000-0e2251febc21792b39182021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00kb-0100490000-75bda764b069c4caf5052021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9200002000-3c5745a1619227a865dc2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056u-9300000000-220ed1ea5f735f87b7882021-09-24View 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 IDNot Available
DrugBank IDNot Available
HMDB IDHMDB41368
CRC / DFC (Dictionary of Food Compounds) IDNQK70-L:NQK74-P
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