CAS 1415-73-2|(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|Aloin(Barbaloin)|Barbaloin|(10S)-1,8-dihydroxy-3-(hy...

General Information

Structure

Molecular Formula

C₂₁H₂₂O₉

Molecular Mass

418.39398

Exact Mass

418.12638228

Charge

InChI

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

Canonic Smiles

OCc1cc(O)c2c(c1)[C@@H]([C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)c1c(C2=O)c(O)ccc1

Isomeric Smiles

[C@@H]1(O[C@H]([C@@H]([C@H]([C@@H]1O)O)O)[C@H]1c2c(C(=O)c3c1cc(cc3O)CO)c(ccc2)O)CO

Calculated Properties

JChem

Acid pKa

9.505504

H Acceptors

H Donor

LogD (pH = 5.5)

0.41494715

LogD (pH = 7.4)

0.4116161

Log P

0.41498974

Molar Refractivity

103.7931

Polarizability

40.31564

Polar Surface Area

167.91

Rotatable Bonds

Lipinski's Rule of Five

false

Data Source

Names and Identifiers

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

Synonyms

Aloin(Barbaloin)BarbaloinAloin1,8-Dihydroxy-10-(β-D-glucopyranosyl)-3-(hydroxymethyl)-9(10H)-anthracenoneAloin A10-β-D-Glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-9(10H)-anthracenoneBarbaloin

IUPAC 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 (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

Names and Identifiers

Registration numbers

CAS Number

EC Number

MDL Number

Beilstein Number

PubChem SID

2489193824890427162037919

PubChem CID

12305761

Registration numbers

Properties

Safety Information

-20°C

P261-P305+P351+P338

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Physical Property

pyridine: soluble50 mg/mL, clear, dark red

Pharmacology Properties

Increase prostaglandin synthesis

Na+, K(+)-adenosine triphosphatase (ATPase) inhibitor

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

Selleck Chemicals

S2375

Research Area: Cancer
Biological Activity:
Aloin(Barbaloin) is a potent tyrosinase inhibitor with an IC50 of 97 µM for HeLaS3 cells. It is used as a stimulant-laxative, treating constipation by inducing bowel movements.It also shows a pronounced antiproliferative effect at physiological concentration, causes cell cycle arrest in the S phase, and markedly increases HeLaS3 cell apoptosis (to 24%). In the concentration range of 20-100 µM, its action was accompanied by remarkable changes in the activity of almost all antioxidant enzymes: MnSOD activity was increased many fold, while CuZnSOD and iNOS activities were inhibited. Moreover, inhibition of CuZnSOD was shown to occur by direct aloin interaction with the enzyme. [1][2]

Sigma Aldrich

A0451

Biochem/physiol Actions
Purgative activity in rats requires activation by Eubacterium sp. strain BAR or similar intestinal anaerobe, presumably by conversion to aloe-emodin anthrone.1

B6906

Application
Aloin, a natural mixed diastereomer (A/B) anthracycline from aloe plant, is studied as an antineoplastic agent that enhances melanogenesis and transglutaminase activity. Aloin A is used as a stabilizer in the preparation of gold and silver nanoparticles.
Biochem/physiol Actions
Purgative activity in rats requires activation by Eubacterium sp. strain BAR or similar intestinal anaerobe, presumably by conversion to aloe-emodin anthrone.1

06088

Biochem/physiol Actions
Purgative activity in rats requires activation by Eubacterium sp. strain BAR or similar intestinal anaerobe, presumably by conversion to aloe-emodin anthrone.1

Molecule Details

References

PubChem Literature

From Data Sources

• Ni??iforovi?? A et al. Cancer Biol Ther. 2007 Aug;6(8):1200-5.

• 2. Ishii Y, Tanizawa H, Takino Y. Studies of aloe. III. Mechanism of cathartic effect. (2). Chem Pharm Bull (Tokyo). 1990 Jan;38(1):197-200.

• Prostaglandins. 1983 Oct;26(4):557-62.

• A purgative action of barbaloin is induced by Eubacterium sp. strain BAR, a human intestinal anaerobe, capable of transforming barbaloin to aloe-emodin anthrone. Biol Pharm Bull. 1996 Jan;19(1):136-8.

• 1. Akao T, Che QM, Kobashi K, Hattori M, Namba T.

• 3. Capasso F, Mascolo N, Autore G, Duraccio MR. Effect of indomethacin on aloin and 1,8 dioxianthraquinone-induced production of prostaglandins in rat isolated colon.

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

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

Synonyms

Aloin(Barbaloin)BarbaloinAloin1,8-Dihydroxy-10-(β-D-glucopyranosyl)-3-(hydroxymethyl)-9(10H)-anthracenoneAloin A10-β-D-Glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-9(10H)-anthracenoneBarbaloin

IUPAC Traditional name

Registration numbers

CAS Number

EC Number

MDL Number

Beilstein Number

PubChem SID

2489193824890427162037919

PubChem CID

12305761

Molecule Details

Selleck Chemicals

S2375

Sigma Aldrich

A0451

Biochem/physiol Actions
Purgative activity in rats requires activation by Eubacterium sp. strain BAR or similar intestinal anaerobe, presumably by conversion to aloe-emodin anthrone.1

B6906

06088

Biochem/physiol Actions
Purgative activity in rats requires activation by Eubacterium sp. strain BAR or similar intestinal anaerobe, presumably by conversion to aloe-emodin anthrone.1

References

PubChem Literature

From Data Sources

• Ni??iforovi?? A et al. Cancer Biol Ther. 2007 Aug;6(8):1200-5.

• 2. Ishii Y, Tanizawa H, Takino Y. Studies of aloe. III. Mechanism of cathartic effect. (2). Chem Pharm Bull (Tokyo). 1990 Jan;38(1):197-200.

• Prostaglandins. 1983 Oct;26(4):557-62.

• 1. Akao T, Che QM, Kobashi K, Hattori M, Namba T.

• 3. Capasso F, Mascolo N, Autore G, Duraccio MR. Effect of indomethacin on aloin and 1,8 dioxianthraquinone-induced production of prostaglandins in rat isolated colon.

Bioactivity

PubChem BioAssay

Properties

Safety Information

-20°C

P261-P305+P351+P338

Download link

Physical Property

pyridine: soluble50 mg/mL, clear, dark red

Pharmacology Properties

Increase prostaglandin synthesis

Na+, K(+)-adenosine triphosphatase (ATPase) inhibitor

Molecule

ID:72999