ChemSpider 2D Image | aloin A | C21H22O9

aloin A

  • Molecular FormulaC21H22O9
  • Average mass418.394 Da
  • Monoisotopic mass418.126373 Da
  • ChemSpider ID24534069

  • defined stereocentres - 6 of 6 defined stereocentres

More details:

Validated by Experts, Validated by Users, Non-Validated, Removed by Users

aloin A
(10S)-10-β-D-Glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-9(10H)-anthracenone
(1S)-1,5-Anhydro-1-[(9S)-4,5-dihydroxy-2-(hydroxymethyl)-10-oxo-9,10-dihydro-9-anthracenyl]-D-glucitol [German] [ACD/IUPAC Name]
(1S)-1,5-Anhydro-1-[(9S)-4,5-dihydroxy-2-(hydroxymethyl)-10-oxo-9,10-dihydro-9-anthracenyl]-D-glucitol [ACD/IUPAC Name]
(1S)-1,5-Anhydro-1-[(9S)-4,5-dihydroxy-2-(hydroxyméthyl)-10-oxo-9,10-dihydro-9-anthracényl]-D-glucitol [French] [ACD/IUPAC Name]
(1S)-1,5-Anhydro-1-[(9S)-4,5-dihydroxy-2-(hydroxymethyl)-10-oxo-9,10-dihydroanthracen-9-yl]-D-glucitol
1,8-Dihydroxy-10-(β-D-glucopyranosyl)-3-(hydroxymethyl)-9(10H)-anthracenone
10-β-D-Glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-9(10H)-anthracenone
215-808-0 [EINECS]
Aloin [Wiki]
More...

Validated by Experts, Validated by Users, Non-Validated, Removed by Users

6077558 [DBID]
648RW354S9 [DBID]
AIDS012598 [DBID]
AIDS-012598 [DBID]
C10305 [DBID]
NSC 227189 [DBID]
NSC 631263 [DBID]
UNII:648RW354S9 [DBID]
UNII-648RW354S9 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Chemical Class:

      A <element>C</element>-glycosyl compound that is <stereo>beta</stereo>-<stereo>D</stereo>-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 9<stereo>S</stereo> diastereoisomer). ChEBI CHEBI:2991
      A 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 diastereoisom er). ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:2991
      A 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 ). ChEBI CHEBI:2991

    • Compound Source:

      Asparagus officinalis PlantCyc CPD-11590
      barbaloin biosynthesis PlantCyc CPD-11590, CPD-11590
      Linum usitatissimum PlantCyc CPD-11590

    • Bio Activity:

      Aloin(Aloin-A; Barbaloin-A) is a natural antitumor anthraquinone glycoside with iron chelating and non-atherogenic activities. MedChem Express
      Aloin(Aloin-A; Barbaloin-A) is a natural antitumor anthraquinone glycoside with iron chelating and non-atherogenic activities.; IC50 value:; Target:; in vitro: Aloin significantly inhibited HUVECs proliferation, migration and tube formation in vitro. MedChem Express HY-N0123
      Aloin(Aloin-A; Barbaloin-A) is a natural antitumor anthraquinone glycoside with iron chelating and non-atherogenic activities.;IC50 value:;Target:;In vitro: Aloin significantly inhibited HUVECs proliferation, migration and tube formation in vitro. suppressed activation of VEGF receptor (VEGFR) 2 and STAT3 phosphorylation in endothelial cells. In addition, the constitutively activated STAT3 protein, and the expression of STAT3-regulated antiapoptotic (Bcl-xL), proliferative (c-Myc), and angiogenic (VEGF) proteins were also down-regulated in response to AL in human SW620 cancer cells [1]. aloin exerted inhibition of cell proliferation, adhesion and invasion abilities of B16-F10 melanoma cells under non-cytotoxic concentrations. Furthermore, aloin induced melanoma cell differentiation through the enhancement of melanogenesis and transglutaminase activity [2].;In vivo: Aloin substantially reduced tumor volumes and weight in vivo mouse xenografts, without obviously toxicity [1]. Aloin MedChem Express HY-N0123
      chrysophanol anthrone -> barbaloin PlantCyc CPD-11590, CPD-11590
      Others MedChem Express HY-N0123

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module, version: 14.00

Density: 1.6±0.1 g/cm3
Boiling Point: 752.6±60.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.6 mmHg at 25°C
Enthalpy of Vaporization: 115.1±3.0 kJ/mol
Flash Point: 268.0±26.4 °C
Index of Refraction: 1.741
Molar Refractivity: 102.5±0.3 cm3
#H bond acceptors: 9
#H bond donors: 7
#Freely Rotating Bonds: 3
#Rule of 5 Violations: 1
ACD/LogP: 1.86
ACD/LogD (pH 5.5): 1.64
ACD/BCF (pH 5.5): 10.26
ACD/KOC (pH 5.5): 182.57
ACD/LogD (pH 7.4): 1.01
ACD/BCF (pH 7.4): 2.41
ACD/KOC (pH 7.4): 42.94
Polar Surface Area: 168 Å2
Polarizability: 40.6±0.5 10-24cm3
Surface Tension: 99.8±3.0 dyne/cm
Molar Volume: 253.9±3.0 cm3

Click to predict properties on the Chemicalize site


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