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

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

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	10 / 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 17 Target ID: CHEMBL1825 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26979254	Inhibitor 8504
bone resorption 7 Target ID: GO:0045453 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26712566	Inhibitor 8504
A431 1 Target ID: CHEMBL1075390 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18672034	Inhibitor 8504
MCF7 22 Target ID: CHEMBL387 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18672034	Inhibitor 8504
Leishmania donovani 13 Target ID: CHEMBL367 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17761408	Inhibitor 8504

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.	2008-12	18672034
Evaluation of antiprotozoal and antimycobacterial activities of the resin glycosides and the other metabolites of Scrophularia cryptophila.	2008-03	17761408

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 `Mon Mar 31 19:58:42 GMT 2025` Edited by `admin` on `Mon Mar 31 19:58:42 GMT 2025`
Record UNII	OF59XHX7SR
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

(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

Preferred Name

English

HARPAGIDE

Official Name

English

Code System Code Type Description

FDA UNII

OF59XHX7SR