Record Information
Creation date2010-04-08 22:10:12 UTC
Update date2019-11-26 03:06:55 UTC
Primary IDFDB012504
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameDemissidine
Description3-epidemissidine belongs to solanidines and derivatives class of compounds. Those are steroids with a structure based on the solanidane skeleton. Solanidane arises from the conversion of a cholestane side-chain into a bicyclic system. 3-epidemissidine is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). 3-epidemissidine can be found in alcoholic beverages, potato, and root vegetables, which makes 3-epidemissidine a potential biomarker for the consumption of these food products.
CAS Number474-08-8
Dihydrosolanidine Tdb_source
Solanidan-3-ol, 9CIdb_source
Solanine Ddb_source
Predicted Properties
Water Solubility0.016 g/LALOGPS
pKa (Strongest Acidic)13.64ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity129.05 m³·mol⁻¹ChemAxon
Polarizability54.51 ųChemAxon
Number of Rings4ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC28H48O5
IUPAC name(2R,5R,16S)-15-[(2S,3R,4R,5S)-3,4-dihydroxy-5,6-dimethylheptan-2-yl]-5-hydroxy-2,16-dimethyl-9-oxatetracyclo[^{2,7}.0^{12,16}]octadecan-8-one
InChI IdentifierInChI=1S/C28H48O5/c1-15(2)16(3)24(30)25(31)17(4)20-7-8-21-19-14-33-26(32)23-13-18(29)9-11-28(23,6)22(19)10-12-27(20,21)5/h15-25,29-31H,7-14H2,1-6H3/t16-,17-,18+,19?,20?,21?,22?,23?,24+,25+,27+,28+/m0/s1
Isomeric SMILES[H][C@](C)(C(C)C)[C@@]([H])(O)[C@]([H])(O)[C@@]([H])(C)C1([H])CCC2([H])C3([H])COC(=O)C4([H])C[C@]([H])(O)CC[C@]4(C)C3([H])CC[C@]12C
Average Molecular Weight464.687
Monoisotopic Molecular Weight464.350174646
Description Belongs to the class of organic compounds known as brassinolides and derivatives. These are cholestane based steroid lactones containing benzo[c]indeno[5,4-e]oxepin-3-one.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroid lactones
Direct ParentBrassinolides and derivatives
Alternative Parents
  • Brassinolide-skeleton
  • Caprolactone
  • Oxepane
  • Cyclic alcohol
  • Carboxylic acid ester
  • Lactone
  • Secondary alcohol
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Alcohol
  • Carbonyl group
  • Organic oxygen compound
  • Organic oxide
  • Organooxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 81.14%; H 11.35%; N 3.50%; O 4.00%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]18D +28 (MeOH)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
EI-MS/GC-MSNot Available
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0019800000-7cd97ecaccaca3c7c30cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-2419100000-c44f5daa433ee7d8a3adSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05u6-9622000000-03d8c0b056e01876dad3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000900000-5b7b5d9dd09b2c049e78Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0102900000-9e1f8b3f4af282b275d9Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02w9-2009500000-c1d901bd4a929c867c0aSpectrum
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 IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDHHN79-K:HHN79-K
EAFUS 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
Biological Effects and Interactions
Health Effects / Bioactivities
anti cholinesterase37733 An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of cholinesterase (EC
anti feedantDUKE
insectifuge24852 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
MSDSNot Available
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).