(+)-Quebrachidine (CHEM024415)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 21:41:07 UTC
Update Date2016-11-09 01:17:53 UTC
Accession NumberCHEM024415
Identification
Common Name(+)-Quebrachidine
ClassSmall Molecule
DescriptionConstituent of Simmondsia chinensis (jojoba) Simmondsin is an extract of jojoba seeds (pronounced "ho-HO-bah") (Simmondsia chinensis), it was traditionally thought to be a toxic substance due to jojoba seed meal causing weight loss in animals, but recently it has been researched as a potential treatment for reducing appetite of obese individuals by helping to reduce craving for food. Several mechanisms of action are thought to be involved in the appetite suppressant effect. Simmondsin is found in coffee and coffee products, fats and oils, and nuts.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
2-Cyanomethylene-1-glucosyloxy-3-hydroxy-4,5-dimethoxycyclohexaneHMDB
[6-(b-D-Glucopyranosyloxy)-2-hydroxy-3,4-dimethoxycyclohexylidene]acetonitrile, 9ciHMDB
2-(Cyanomethylene)-3-hydroxy-4,5-dimethoxycyclohexyl-beta-glucosideHMDB
Methyl (10S,13E,16S,18S)-13-ethylidene-18-hydroxy-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6-triene-17-carboxylic acidGenerator
Chemical FormulaC21H24N2O3
Average Molecular Mass352.427 g/mol
Monoisotopic Mass352.179 g/mol
CAS Registry Number21641-60-1
IUPAC Namemethyl (10S,13E,16S,18S)-13-ethylidene-18-hydroxy-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6-triene-17-carboxylate
Traditional Namemethyl (10S,13E,16S,18S)-13-ethylidene-18-hydroxy-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6-triene-17-carboxylate
SMILESCOC(=O)C12[C@@H]3CC4(C(NC5=CC=CC=C45)[C@@H]4CC1\C(CN34)=C/C)[C@@H]2O
InChI IdentifierInChI=1S/C21H24N2O3/c1-3-11-10-23-15-8-13(11)21(19(25)26-2)16(23)9-20(18(21)24)12-6-4-5-7-14(12)22-17(15)20/h3-7,13,15-18,22,24H,8-10H2,1-2H3/b11-3-/t13?,15-,16-,17?,18-,20?,21?/m0/s1
InChI KeyRLUORQGMBKDXPO-CFAUMIGUSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentO-glycosyl compounds
Alternative Parents
Substituents
  • Hexose monosaccharide
  • O-glycosyl compound
  • Cyclitol or derivatives
  • Monosaccharide
  • Oxane
  • Cyclic alcohol
  • Secondary alcohol
  • Polyol
  • Acetal
  • Organoheterocyclic compound
  • Nitrile
  • Carbonitrile
  • Oxacycle
  • Ether
  • Dialkyl ether
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic nitrogen compound
  • Alcohol
  • Primary alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.17 g/LALOGPS
logP2.38ALOGPS
logP1.2ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)13.85ChemAxon
pKa (Strongest Basic)6.98ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area61.8 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity98.85 m³·mol⁻¹ChemAxon
Polarizability38.08 ųChemAxon
Number of Rings6ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0076-3049000000-1512485f53dac99bd342Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05g3-9004200000-c80d0efaafffc8a45e86Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udr-0009000000-861a7ed16f2918f700dcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ug0-0029000000-0985fd508474fa418573Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-2096000000-e2bc058d27a511d00e0fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-00bda9e8ec0b8b34a52aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0019000000-fb75b362b0dd374df4c7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ko-0093000000-62d75063c7fd5ac92e6eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0019000000-40c487ceb6e346a1aed9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0029000000-db598bf64510018ca56eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udl-0069000000-8a9e1f50c6e35e081fcfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0049000000-63bd1a6a9039fd137926Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0090000000-a47e1d5b96b417632a5cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-0090000000-4e71703a18aaccacc836Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0030394
FooDB IDFDB002248
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkSimmondsin
Chemspider ID4733931
ChEBI IDNot Available
PubChem Compound ID5884740
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.