HARPAGIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C15H24O10
Molecular Weight	364.3451
Optical Activity	UNSPECIFIED
Defined Stereocenters	10 / 10
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@]12[C@H](O[C@]3([H])O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)OC=C[C@@]1(O)[C@H](O)C[C@]2(C)O

InChI

InChIKey=XUWSHXDEJOOIND-YYDKPPGPSA-N

InChI=1S/C15H24O10/c1-14(21)4-7(17)15(22)2-3-23-13(11(14)15)25-12-10(20)9(19)8(18)6(5-16)24-12/h2-3,6-13,16-22H,4-5H2,1H3/t6-,7-,8-,9+,10-,11-,12+,13+,14+,15-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C15H24O10
Molecular Weight	364.3451
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	9 / 10
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22940241
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/18672034 https://www.ncbi.nlm.nih.gov/pubmed/17761408

Harpagide and harpagoside are two iridoid glycosides existing in many medicinal plants. They are believed to be the main bioactive compounds related to the anti-inflammatory efficacy of these plants. In vitro Harpagide has shown cytotoxic activity against tumor cell lines A431, HeLa and MCF7. Harpagide emerged as a leishmanicidal agent. Harpagide is common in nature and is known to possess anti-inflammatory activity. In addition, it has been shown that the hydrolysed products of harpagoside and harpagide have more pronounced anti-inflammatory activity when compared to the unhydrolysed compounds.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
TNF-alpha 18 Target ID: CHEMBL1825 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26979254	Inhibitor 8297
bone resorption 7 Target ID: GO:0045453 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26712566	Inhibitor 8297
A431 1 Target ID: CHEMBL1075390 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18672034	Inhibitor 8297
MCF7 21 Target ID: CHEMBL387 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18672034	Inhibitor 8297
Leishmania donovani 13 Target ID: CHEMBL367 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17761408	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bone destruction disease 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26712566	Primary		Basic research	Unknown Approved Use Unknown
Leishmaniasis 20 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17761408	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Cytotoxic activities of Stachys species.	2008 Dec	18672034

Patents

Sample Use Guides

In Vivo Use Guide

Rats received orally 15 mg/kg (equivalent of 1.5mg/kg harpagide) of Ajuga decumbens Thunb extract.

Route of Administration: Oral

In Vitro Use Guide

Harpagide at 90ug/mL inhibited HeLa cell proliferation (55.94%)

Substance Class	Chemical Created by `admin` on `Fri Dec 15 19:50:54 GMT 2023` Edited by `admin` on `Fri Dec 15 19:50:54 GMT 2023`
Record UNII	OF59XHX7SR
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

HARPAGIDE

Official Name

English

HARPAGIDE [INCI]

Common Name

English

(1S-(1A,4AA,5A,7A,7A))-1,4A,5,6,7,7A-HEXAHYDRO-4A,5,7-TRIHYDROXY-7-METHYLCYCLOPENTA(C)PYRAN-1-YL BETA-D-GLUCOPYRANOSIDE

Common Name

English

Code System Code Type Description

FDA UNII

OF59XHX7SR