HECOGENIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C27H42O4
Molecular Weight	430.62
Optical Activity	UNSPECIFIED
Defined Stereocenters	12 / 12
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@]12C[C@@]3([H])[C@]4([H])CC[C@@]5([H])C[C@@H](O)CC[C@]5(C)[C@@]4([H])CC(=O)[C@]3(C)[C@@]1([H])[C@H](C)[C@@]6(CC[C@@H](C)CO6)O2

InChI

InChIKey=QOLRLLFJMZLYQJ-LOBDNJQFSA-N

InChI=1S/C27H42O4/c1-15-7-10-27(30-14-15)16(2)24-22(31-27)12-21-19-6-5-17-11-18(28)8-9-25(17,3)20(19)13-23(29)26(21,24)4/h15-22,24,28H,5-14H2,1-4H3/t15-,16+,17+,18+,19-,20+,21+,22+,24+,25+,26-,27-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C27H42O4
Molecular Weight	430.62
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	11 / 12
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22426163
Curator's Comment: description was created based on several sources, including: https://www.ncbi.nlm.nih.gov/pubmed/25115457

Hecogenin is the steroidal saponin aglycone (or sapogenin) present in the leaves of species from the Agave genus, including Agave sisalana, Agave cantala and Agave aurea. Hecogenin has a wide spectrum of pharmacological activities already studied, including anticancer/antiproliferative, antifungal and hipotensive activities. A recent study showed that this substance is a selective inhibitor of human UDP-glucuronosyltransferases, enzymes responsible for the detoxification of numerous chemical toxins

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
UDP-glucuronosyltransferase 1A4 1 Target ID: CHEMBL3619 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25448279	Inhibitor 8297		4.2 µM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Prostata hyperplasia 1 Sources: https://www.google.com/patents/US5002939	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Glucuronidation, a new metabolic pathway for pyrrolizidine alkaloids.	2010 Mar 15	20092275
In vitro selective inhibition of human UDP-glucuronosyltransferase (UGT) 1A4 by finasteride, and prediction of in vivo drug-drug interactions.	2015 Jan 22	25448279

Patents

Sample Use Guides

In Vivo Use Guide

The anti-inflammatory effects of Hecogenin (50 µg/animal) was investigated on various inflammatory models. The anti-inflammatory effect of HG, was studied on % inhibition of dry weight of granuloma tissue, Δ ear weight, myeloperoxidase assay, serum pro-inflammatory cytokines, colon weight to length ratio, macroscopic lesions, adhesion score, diarrhoea score and histopathological analysis of ear and colon tissue on Cotton pellets induced granuloma in rats, Croton oil induced ear edema in mice and TNBS induced granuloma in rats.

Route of Administration: Topical

In Vitro Use Guide

UGT1A4 inhibition by hecogenin (0-20 µM) was evaluated in imipramine N-beta-D-glucuronidation assay.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 09:17:03 GMT 2023` Edited by `admin` on `Sat Dec 16 09:17:03 GMT 2023`
Record UNII	3XP44JJ79F
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

HECOGENIN

Common Name

English

SPIROSTAN-12-ONE, 3-HYDROXY-, (3.BETA.,5.ALPHA.,25R)-

Common Name

English

12-OXOTIGOGENIN

Common Name

English

(+)-HECOGENIN

Common Name

English

HEKOGENIN

Common Name

English

HECOGENIN [MI]

Common Name

English

GEKOGENIN

Common Name

English

HOCOGENIN

Common Name

English

NSC-115921

Code

English

25(R)-3.BETA.-HYDROXYSPIROSTAN-12-ONE

Common Name

English

Classification Tree Code System Code

DSLD

3773 (Number of products:2)