Aloin A (CHEM018673)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 05:26:21 UTC
Update Date2016-11-09 01:15:51 UTC
Accession NumberCHEM018673
Identification
Common NameAloin A
ClassSmall Molecule
DescriptionA C-glycosyl compound that is beta-D-glucopyranose in which the anomeric hydroxy group is replaced by a 4,5-dihydroxy-2-(hydroxymethyl)-10-oxo-9,10-dihydroanthracen-9-yl moiety (the 9S diastereoisomer).
Contaminant Sources
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
BarbaloinChEBI
AloinKegg
IsobarbaloinMeSH
Barbaloin, monoglucosideMeSH
Barbaloin, (S)-isomerMeSH
Barbaloin, beta-D-isomerMeSH
Aloin aMeSH, KEGG
AlloinMeSH
Chemical FormulaC21H22O9
Average Molecular Mass418.398 g/mol
Monoisotopic Mass418.126 g/mol
CAS Registry Number1415-73-2
IUPAC Name(10S)-1,8-dihydroxy-3-(hydroxymethyl)-10-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-9,10-dihydroanthracen-9-one
Traditional Name(10S)-1,8-dihydroxy-3-(hydroxymethyl)-10-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-10H-anthracen-9-one
SMILES[H][C@]1(CO)O[C@]([H])([C@]([H])(O)[C@@]([H])(O)[C@]1([H])O)[C@@]1([H])C2=C(C(O)=CC=C2)C(=O)C2=C1C=C(CO)C=C2O
InChI IdentifierInChI=1S/C21H22O9/c22-6-8-4-10-14(21-20(29)19(28)17(26)13(7-23)30-21)9-2-1-3-11(24)15(9)18(27)16(10)12(25)5-8/h1-5,13-14,17,19-26,28-29H,6-7H2/t13-,14+,17-,19+,20-,21+/m1/s1
InChI KeyAFHJQYHRLPMKHU-OSYMLPPYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as anthracenes. These are organic compounds containing a system of three linearly fused benzene rings.
KingdomOrganic compounds
Super ClassBenzenoids
ClassAnthracenes
Sub ClassNot Available
Direct ParentAnthracenes
Alternative Parents
Substituents
  • Anthracene
  • Hexose monosaccharide
  • C-glycosyl compound
  • Glycosyl compound
  • Aryl ketone
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monosaccharide
  • Oxane
  • Vinylogous acid
  • Ketone
  • Secondary alcohol
  • Dialkyl ether
  • Ether
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic oxide
  • Aromatic alcohol
  • Organooxygen compound
  • Primary alcohol
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
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 Solubility2.63 g/LALOGPS
logP-0.49ALOGPS
logP0.41ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)8.31ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area167.91 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity103.79 m³·mol⁻¹ChemAxon
Polarizability40.26 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uxr-0011900000-39e8580ac4039b03626aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uyi-2396700000-179c1fc7b88c9c7c5c1eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-067r-3193000000-3c8d2553499a4566d0a0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-1146900000-45b4e6801923df86f787Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00rb-5339200000-d7863f53d29ddba771a0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9081000000-3020c577e1e2f5e2b409Spectrum
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 IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDC00002797
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkAloin
Chemspider IDNot Available
ChEBI ID2991
PubChem Compound ID12305761
Kegg Compound IDC10305
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=17269040
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=23569857
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=3246014