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Showing Compound (3beta,5alpha,6alpha)-Cholest-8-ene-3,6-diol (FDB000381)

Record Information
Version1.0
Creation date2010-04-08 22:04:33 UTC
Update date2019-11-26 02:54:42 UTC
Primary IDFDB000381
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(3beta,5alpha,6alpha)-Cholest-8-ene-3,6-diol
Description3,6-Ditigloyloxytropan-7-ol belongs to the class of organic compounds known as tropane alkaloids. These are organic compounds containing the nitrogenous bicyclic alkaloid parent N-Methyl-8-azabicyclo[3.2.1]octane. 3,6-Ditigloyloxytropan-7-ol is a very strong basic compound (based on its pKa). 3,6-Ditigloyloxytropan-7-ol has been detected, but not quantified in, fruits. This could make 3,6-ditigloyloxytropan-7-ol a potential biomarker for the consumption of these foods.
CAS Number570-92-3
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
PeniocerolHMDB
(3b,5a,6a)-Cholest-8-ene-3,6-diolGenerator
(3Β,5α,6α)-cholest-8-ene-3,6-diolGenerator
Predicted Properties
PropertyValueSource
Water Solubility0.0033 g/LALOGPS
logP5.69ALOGPS
logP5.76ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)14.7ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity121.94 m³·mol⁻¹ChemAxon
Polarizability51.15 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC27H46O2
IUPAC name2,15-dimethyl-14-(6-methylheptan-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-ene-5,8-diol
InChI IdentifierInChI=1S/C27H46O2/c1-17(2)7-6-8-18(3)21-9-10-22-20-16-25(29)24-15-19(28)11-13-27(24,5)23(20)12-14-26(21,22)4/h17-19,21-22,24-25,28-29H,6-16H2,1-5H3
InChI KeyMPCLLXXLNXORCU-UHFFFAOYSA-N
Isomeric SMILESCC(C)CCCC(C)C1CCC2C3=C(CCC12C)C1(C)CCC(O)CC1C(O)C3
Average Molecular Weight402.6529
Monoisotopic Molecular Weight402.349780716
Classification
Description Belongs to the class of organic compounds known as tropane alkaloids. These are organic compounds containing the nitrogenous bicyclic alkaloid parent N-Methyl-8-azabicyclo[3.2.1]Octane.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassTropane alkaloids
Sub ClassNot Available
Direct ParentTropane alkaloids
Alternative Parents
Substituents
  • Tropane alkaloid
  • Fatty acid ester
  • Dicarboxylic acid or derivatives
  • Piperidine
  • Fatty acyl
  • N-alkylpyrrolidine
  • Cyclic alcohol
  • Pyrrolidine
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • 1,2-aminoalcohol
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Secondary alcohol
  • Tertiary amine
  • Tertiary aliphatic amine
  • Carboxylic acid derivative
  • Azacycle
  • Organoheterocyclic compound
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Amine
  • Alcohol
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect

Health effect:

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 80.54%; H 11.51%; O 7.95%DFC
Melting PointMp 181-183°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D +59 (c, 0.76 in CHCl3)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS(3beta,5alpha,6alpha)-Cholest-8-ene-3,6-diol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-059l-1119000000-db16c092622bf65d05feSpectrum
Predicted GC-MS(3beta,5alpha,6alpha)-Cholest-8-ene-3,6-diol, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001i-4100590000-87069b854115f58cbdddSpectrum
Predicted GC-MS(3beta,5alpha,6alpha)-Cholest-8-ene-3,6-diol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3beta,5alpha,6alpha)-Cholest-8-ene-3,6-diol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f79-0009200000-2aa46a31e8be5e8a3b122016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-3139100000-a0b4a7bb6646e6e925062016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9367000000-3741596db93a263a0e492016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0003900000-fc1163406506bd489d6a2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ue9-0009800000-ebe84469a7b3a7da6d4a2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ku-3009000000-c2668c4ef5835446ae982016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0004900000-401101a259287addc3f22021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0k96-9142200000-d968e3ace673036921982021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9620000000-d2ed767dd84decf906cd2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000900000-079f76b4d985e4b92c9d2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0000900000-079f76b4d985e4b92c9d2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-0007900000-9e5898d1a9b86b4a7ec22021-09-25View Spectrum
NMRNot Available
ChemSpider ID11568064
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID5389314
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB29320
CRC / DFC (Dictionary of Food Compounds) IDHGJ81-E:BBP23-V
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00035362
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