Natural Product (NP) Details

General Information of the NP (ID: NP6628)
Name
Aloin
Synonyms
Barbaloin; aloin; 1415-73-2; Aloin A; Barbaloin A; Aloinum; UNII-648RW354S9; Aloin (Mixture of A and B); CHEBI:2991; MFCD00151160; 1,8-Dihydroxy-3-hydroxymethyl-10-(6-hydroxymethyl-3,4,5-trihydroxy-2-pyranyl)anthrone; Aloin [BAN]; 648RW354S9; DSSTox_CID_25967; (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; (1S)-1,5-anhydro-1-[(9S)-4,5-dihydroxy-2-(hydroxymethyl)-10-oxo-9,10-dihydroanthracen-9-yl]-D-glucitol; (S)-1,8-dihydroxy-3-(hydroxymethyl)-10-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)anthracen-9(10H)-one; 10-(1',5'-Anhydroglucosyl)aloe-emodin-9-anthrone; NSC631263; 10-Glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-9(10H)-anthracenone; Barbaloin,(S); NCGC00183867-01; Aloin (Barbaloin); 8015-61-0; EINECS 215-808-0; NSC 227189; NSC 631263; Aloin, analytical standard; DSSTox_RID_81262; DSSTox_RID_82951; DSSTox_GSID_45967; DSSTox_GSID_48755; CHEMBL2103763; DTXSID0045967; SCHEMBL14837254; 10-beta-D-Glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-9(10H)-anthracenone; 9(10H)-Anthracenone, 10-beta-D-glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-, (10S)-; Aloin, from Curacao aloe, ~50%; HY-N0123; Tox21_111495; Tox21_113216; s2375; AKOS022168218; ZINC100018557; CCG-268870; CS-3707; NSC 407305; NSC 758464; (R)-10-beta-D-Glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)anthracen-9(10H)-one; 9(10H)-Anthracenone, 10-.beta.-D-glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-, (S)-; CAS-1415-73-2; CAS-8015-61-0; FT-0772660; N2491; C10305; 415B732; A807778; Q413888; Aloin, from Aloe barbadensis Miller leaves, >=97%; Aloin, United States Pharmacopeia (USP) Reference Standard; UNII-W41H6S09F4 component AFHJQYHRLPMKHU-OSYMLPPYSA-N; 10-Glucopyranosyl-1,8-dihydro-3-(hydroxymethyl)-9-anthracenone; 1,8-Dihydroxy-10-(bet.-D-glucopyranosyl)-3-(hydroxymethyl)-9(10H)-anthracenone; 1,8-Dihydroxy-10-(beta-D-glucopyranosyl)-3-(hydroxymethyl)-9(10H)-anthracenone; 10-.BETA.-D-Glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-9(10H)-anthracenone-, 10(S)-; 10-beta-D-Glucopyranosyl-1,8-dihydroxy-3-hydroxymethyl-9(10H)-anthrone,(R)-; (10S)-1,8-dihydroxy-3-(hydroxymethyl)-10-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)-2-oxanyl]-10H-anthracen-9-one; (10S)-1,8-dihydroxy-3-(hydroxymethyl)-10-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]-10H-anthracen-9-one; (10S)-3-(hydroxymethyl)-10-[(2S,3R,4R,5S,6R)-6-(hydroxymethyl)-3,4,5-tris(oxidanyl)oxan-2-yl]-1,8-bis(oxidanyl)-10H-anthracen-9-one
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Species Origin Aloe Vera ...     Click to Show/Hide
Aloe Vera
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Asparagales
Family: Asphodelaceae
Genus: Aloe
Species: Aloe Vera
Disease Solid tumour/cancer [ICD-11: 2A00-2F9Z] Investigative [1]
Structure
Click to Download Mol
2D MOL

3D MOL

ADMET Property
Absporption
Caco-2 Permeability
 -6.268
 
MDCK Permeability
 -5.044
 
PAMPA
 +++
 
HIA
 +
 
Distribution
VDss
 -0.038
 
PPB
 81.6%
 
BBB
 - - -
 
Metabolism
CYP1A2 inhibitor
 - - -
CYP1A2 substrate
 - - -
CYP2C19 inhibitor
 - - -
CYP2C19 substrate
 - - -
CYP2C9 inhibitor
 - - -
CYP2C9 substrate
 - - -
CYP2D6 inhibitor
 - -
CYP2D6 substrate
 - - -
CYP3A4 inhibitor
 - - -
CYP3A4 substrate
 +
CYP2B6 inhibitor
 - - -
CYP2B6 substrate
 - - -
CYP2C8 inhibitor
 +++
HLM Stability
 -
 
Excretion
CLplasma
 2.634
 
T1/2
 2.49
Toxicity
DILI
 +
 
Rat Oral Acute Toxicity
 - - -
 
FDAMDD
 - - -
 
Respiratory
 - -
 
Human Hepatotoxicity
 +
 
Ototoxicity
 +++
 
Drug-induced Nephrotoxicity
 +++
 
Drug-induced Neurotoxicity
 - - -
 
Hematotoxicity
 -
 
Genotoxicity
 +++
 
Tips: 1. For the classification endpoints, the prediction probability values are transformed into six symbols: 0-0.1 (- - -), 0.1-0.3 (- -), 0.3-0.5 (-), 0.5-0.7 (+), 0.7-0.9 (++), and 0.9-1.0 (+++). 2. Additionally, the corresponding relationships of the three labels are as follows: excellent; medium; poor.
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    Click to Show/Hide the Molecular Information and External Link(s) of This Natural Product
Formula
C21H22O9
PubChem CID
12305761
Canonical SMILES
C1=CC2=C(C(=C1)O)C(=O)C3=C(C2C4C(C(C(C(O4)CO)O)O)O)C=C(C=C3O)CO
InChI
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
InChIKey
AFHJQYHRLPMKHU-OSYMLPPYSA-N
CAS Number
CAS 1415-73-2
ChEBI ID
CHEBI:2991
Herb ID
HBIN015313
SymMap ID
SMIT01266
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          Cisplatin      Bladder cancer     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Up-regulation Expression TG2  Molecule Info 
Pathway MAP
Up-regulation Expression TYR  Molecule Info 
Pathway MAP
                    In-vitro Model B16-F10 CVCL_0159 Mouse melanoma Mus musculus
                    Experimental
                    Result(s)		 Aloin enhances cisplatin antineoplastic activity in B16-F10 melanoma cells by transglutaminase-induced differentiation.
    β. A List of Drug(s) Whose Adverse Effect can be Decreased by This NP
          Doxorubicin      Solid tumour/cancer     Click to Show/Hide the Molecular Data of This Drug
                 Decreasing Adverse Drug Reaction     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Expression IL19  Molecule Info 
Pathway MAP
Down-regulation Secretion IL1B  Molecule Info 
Pathway MAP
Down-regulation Secretion IL6  Molecule Info 
Pathway MAP
Down-regulation Secretion TNF  Molecule Info 
Pathway MAP
                    Biological
                    Regulation		 Inhibition DOX-induced rise in MAB
                    In-vivo Model Male Wistar rats (150-200 g, age 6-8 weeks) were used in this study.
                    Experimental
                    Result(s)		 Aloin alleviates doxorubicin-induced cardiotoxicity in rats by abrogating oxidative stress and pro-inflammatory cytokines.
References
Reference 1 Suppressive effects of aloin on polyphosphate-mediated vascular inflammatory responses. J Asian Nat Prod Res. 2021 Jan;23(1):89-99.
Reference 2 Aloin enhances cisplatin antineoplastic activity in B16-F10 melanoma cells by transglutaminase-induced differentiation. Amino Acids. 2013 Jan;44(1):293-300.
Reference 3 Aloin alleviates doxorubicin-induced cardiotoxicity in rats by abrogating oxidative stress and pro-inflammatory cytokines. Cancer Chemother Pharmacol. 2020 Sep;86(3):419-426.
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