.ALPHA.-ESCIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C55H86O24
Molecular Weight	1131.2569
Optical Activity	UNSPECIFIED
Defined Stereocenters	27 / 27
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]8(O[C@H]1[C@H](O)[C@@H](O[C@]2([H])O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@]([H])(O[C@H]3CC[C@@]4(C)[C@@]([H])(CC[C@]5(C)[C@]4([H])CC=C6[C@]7([H])CC(C)(C)[C@@H](OC(=O)C(\C)=C\C)[C@H](OC(C)=O)[C@]7(CO)[C@H](O)C[C@@]56C)[C@@]3(C)CO)O[C@@H]1C(O)=O)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]8O

InChI

InChIKey=AXNVHPCVMSNXNP-IVKVKCDBSA-N

InChI=1S/C55H86O24/c1-10-23(2)46(71)79-43-44(72-24(3)60)55(22-59)26(17-50(43,4)5)25-11-12-30-51(6)15-14-32(52(7,21-58)29(51)13-16-53(30,8)54(25,9)18-31(55)61)75-49-41(77-48-38(67)36(65)34(63)28(20-57)74-48)39(68)40(42(78-49)45(69)70)76-47-37(66)35(64)33(62)27(19-56)73-47/h10-11,26-44,47-49,56-59,61-68H,12-22H2,1-9H3,(H,69,70)/b23-10+/t26-,27+,28+,29+,30+,31+,32-,33+,34+,35-,36-,37+,38+,39-,40-,41+,42-,43-,44-,47-,48-,49+,51-,52+,53+,54+,55-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C55H86O24
Molecular Weight	1131.2569
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	27 / 27
E/Z Centers	1
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11529685 | https://www.ncbi.nlm.nih.gov/pubmed/24689224https://www.ncbi.nlm.nih.gov/pubmed/10949118 | https://www.ncbi.nlm.nih.gov/pubmed/27008697 | https://www.ncbi.nlm.nih.gov/pubmed/22094055 | https://www.ncbi.nlm.nih.gov/pubmed/11529685

A-escin (Escin Ia) and isoescin Ia have been traditionally used clinically as the chief active ingredients of escin, a major triterpene saponin isolated from horse chestnut (Aesculus hippocastanum) seeds for the treatment of chronic venous insufficiency, hemorrhoids, inflammation and edema. A-escin administration to prednisolone-treated rats slightly reduced the unfavorable effects of prednisolone on width of periosteal and endosteal osteoid and periosteal transverse growth in the tibia. A-escin suppresses the metastasis of triple-negative breast cancer by inhibiting epithelial-mesenchymal transition via down-regulating LOXL2 expression. Escin Ia has being shown to inhibit pancreatic lipase.

Approval Year

Targets

Primary Target	Pharmacology	Potency
Lysyl oxidase homolog 2 4 Target ID: Q9Y4K0 Gene ID: 4017.0 Gene Symbol: LOXL2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/27008697	Inhibitor 8297
Protease 7 Target ID: CHEMBL2366517 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10579862	Inhibitor 8297	35.0 µM [IC50]
Pancreatic triacylglycerol lipase 12 Target ID: P00591 Gene ID: NA Gene Symbol: PNLIP Target Organism: Sus scrofa (Pig) Sources: https://www.ncbi.nlm.nih.gov/pubmed/16621416	Inhibitor 8297
Protease 7 Target ID: CHEMBL2366517 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10579862	Inhibitor 8297	50.0 µM [IC50]
Pancreatic triacylglycerol lipase 12 Target ID: P00591 Gene ID: NA Gene Symbol: PNLIP Target Organism: Sus scrofa (Pig) Sources: https://www.ncbi.nlm.nih.gov/pubmed/16621416	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Osteopenia 5 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11126622 https://www.ncbi.nlm.nih.gov/pubmed/10949118	Secondary	Preclinical	Unknown Approved Use Unknown
Breast cancer 434 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27008697	Primary	Basic research	Unknown Approved Use Unknown
Obesity 203 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16621416	Primary	Preclinical	Unknown Approved Use Unknown
Obesity 203 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16621416	Primary	Preclinical	Unknown Approved Use Unknown
Lymphedema of arm 4 Sources: https://clinicaltrials.gov/ct2/show/NCT00213928 https://www.ncbi.nlm.nih.gov/pubmed/11529685	Primary	Phase II 1132	Unknown Approved Use Unknown
Chronic venous insufficiency 12 Sources: https://clinicaltrials.gov/ct2/show/NCT02346058 https://www.ncbi.nlm.nih.gov/pubmed/11529685	Primary	Phase IV 63	Unknown Approved Use Unknown
Varicose veins 6 Sources: https://clinicaltrials.gov/ct2/show/NCT02346058 https://www.ncbi.nlm.nih.gov/pubmed/11529685	Primary	Phase IV 63	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
[Substances contained in horse-chestnut seeds. 8. The acylaglycones of cryptoescin and alpha-escin].	1970 Sep	5475947
Influence of alpha-escin on the femoral bone strength in ovariectomized rats.	1999 Nov-Dec	10817529
Effects of alpha-escin on histomorphometrical parameters of long bones in rats with experimental post-steroid osteopenia.	2000 Jan-Feb	10949118
Anti-obesity effects of escins extracted from the seeds of Aesculus turbinata BLUME (Hippocastanaceae).	2008 Jan	18175967
A liquid chromatography-tandem mass spectrometry method for the simultaneous quantification of escin Ia and escin Ib in human plasma: application to a pharmacokinetic study after intravenous administration.	2010 Dec	20662111
Comparative pharmacokinetics and the bioavailability of escin Ib and isoescin Ib following the administration of escin, pure escin Ib and isoescin Ib in rats.	2014 Feb 3	24334163
Escin Ia suppresses the metastasis of triple-negative breast cancer by inhibiting epithelial-mesenchymal transition via down-regulating LOXL2 expression.	2016 Apr 26	27008697

Patents

Sample Use Guides

In Vivo Use Guide

Mice: Gastric emptying (GE) inhibition by b-escin (escin Ib) (25 mg/kg, p.o.) was attenuated after pretreatment with a single bolus of DL-alpha-methyl-p-tyrosine methyl ester

Route of Administration: Oral

In Vitro Use Guide

In human saphenous veins in vitro, venotonic properties were well confirmed with purified β-aescin. Achieved contractures are maximal at concentrations of 10(−3) M but are already quite evident at 10(−6)–10(−7) M. Aescin, at concentrations of 10(−3 M) or lower resulted in a clear increase of contractility in human isolated saphenous veins.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 19:02:25 GMT 2023` Edited by `admin` on `Fri Dec 15 19:02:25 GMT 2023`
Record UNII	LB5DJT9FIW
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

.ALPHA.-ESCIN

Common Name

English

ESCIN .ALPHA.-ESCIN [MI]

Common Name

English

ALPHA-ESCIN

Common Name

English

AESCIN A

Common Name

English

ESCIN .ALPHA.-ESCIN

Common Name

English

ESCIN IA (CONSTITUENT OF HORSE CHESTNUT) [DSC]

Common Name

English

.BETA.-D-GLUCOPYRANOSIDURONIC ACID, (3.BETA.,4.BETA.,16.ALPHA.,21.BETA.,22.ALPHA.)-22-(ACETYLOXY)-16,23,28-TRIHYDROXY-21-(((2E)-2-METHYL-1-OXO-2-BUTEN-1-YL)OXY)OLEAN-12-EN-3-YL O-.BETA.-D-GLUCOPYRANOSYL-(1->2)-O-(.BETA.-D-GLUCOPYRANOSYL-(1->4))-

Systematic Name

English

.ALPHA.-AESCIN

Common Name

English

ESCIN IA

Common Name

English

Code System Code Type Description

PUBCHEM

6476030