Record Information
Version1.0
Creation date2010-04-08 22:05:34 UTC
Update date2019-11-26 02:58:08 UTC
Primary IDFDB002915
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameGentiobiose
DescriptionAllolactose is a member of the class of compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol. Allolactose is an inducer of the lac operon in Escherichia coli and many other enteric bacteria. It binds to a subunit of the tetrameric lac repressor, which results in conformational changes and reduces the binding affinity of the lac repressor to the lac operator, thereby dissociating it from the lac operator. The absence of the repressor allows the transcription of the lac operon to proceed. A non-hydrolyzable analog of allolactose, isopropyl β-D-1-thiogalactopyranoside (IPTG), is normally used in molecular biology to induce the lac operon .
CAS Number554-91-6
Structure
Thumb
Synonyms
SynonymSource
Amygdalosedb_source
Gentiobiose, 8CIdb_source
Predicted Properties
PropertyValueSource
Water Solubility511 g/LALOGPS
logP-3ALOGPS
logP-5.3ChemAxon
logS0.17ALOGPS
pKa (Strongest Acidic)11.93ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area197.37 ŲChemAxon
Rotatable Bond Count17ChemAxon
Refractivity69.76 m³·mol⁻¹ChemAxon
Polarizability31.88 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC36H66O33
IUPAC name2,3,4,5-tetrahydroxy-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hexanal; 2-[2-hydroxy-2-(3,4,5-trihydroxyoxolan-2-yl)ethoxy]-6-(hydroxymethyl)oxane-3,4,5-triol; 6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxane-2,3,4,5-tetrol
InChI IdentifierInChI=1S/3C12H22O11/c13-1-4-5(15)6(16)9(19)12(22-4)21-2-3(14)10-7(17)8(18)11(20)23-10;13-1-3-5(14)8(17)10(19)12(23-3)21-2-4-6(15)7(16)9(18)11(20)22-4;13-1-4(15)7(17)8(18)5(16)3-22-12-11(21)10(20)9(19)6(2-14)23-12/h2*3-20H,1-2H2;1,4-12,14-21H,2-3H2
InChI KeyYFSMDFMEDLKMOS-UHFFFAOYSA-N
Isomeric SMILESOCC1OC(OCC(O)C(O)C(O)C(O)C=O)C(O)C(O)C1O.OCC1OC(OCC(O)C2OC(O)C(O)C2O)C(O)C(O)C1O.OCC1OC(OCC2OC(O)C(O)C(O)C2O)C(O)C(O)C1O
Average Molecular Weight1026.8894
Monoisotopic Molecular Weight1026.348634638
Classification
Description belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl glycosides
Direct ParentFatty acyl glycosides of mono- and disaccharides
Alternative Parents
Substituents
  • Fatty acyl glycoside of mono- or disaccharide
  • Alkyl glycoside
  • Disaccharide
  • O-glycosyl compound
  • Glycosyl compound
  • Beta-hydroxy aldehyde
  • Oxane
  • Alpha-hydroxyaldehyde
  • Tetrahydrofuran
  • Secondary alcohol
  • Hemiacetal
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Organic oxygen compound
  • Organooxygen compound
  • Primary alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Aldehyde
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkNot Available
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 42.11%; H 6.48%; O 51.42%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-9000000000-bc2f3b600f60e687a46aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-9000000000-bc2f3b600f60e687a46aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-9000000000-bc2f3b600f60e687a46aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-9000000000-e5a67b632bb21e28d52dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-e5a67b632bb21e28d52dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-e5a67b632bb21e28d52dJSpectraViewer
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) IDCPD88-P:CPD88-P
EAFUS IDNot Available
Dr. Duke IDGENTIOBIOSE
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
Flavours
FlavorCitations
bitter
  1. Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
Files
MSDSNot Available
References
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).