.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

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

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.

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