GITOGENIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C27H44O4
Molecular Weight	432.6359
Optical Activity	UNSPECIFIED
Defined Stereocenters	13 / 13
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@H]1[C@H]2[C@H](C[C@H]3[C@@H]4CC[C@H]5C[C@@H](O)[C@H](O)C[C@]5(C)[C@H]4CC[C@]23C)O[C@]16CC[C@@H](C)CO6

InChI

InChIKey=FWCXELAAYFYCSR-RYKNUXCGSA-N

InChI=1S/C27H44O4/c1-15-7-10-27(30-14-15)16(2)24-23(31-27)12-20-18-6-5-17-11-21(28)22(29)13-26(17,4)19(18)8-9-25(20,24)3/h15-24,28-29H,5-14H2,1-4H3/t15-,16+,17+,18-,19+,20+,21-,22-,23+,24+,25+,26+,27-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C27H44O4
Molecular Weight	432.6359
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	13 / 13
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24530871 | https://www.ncbi.nlm.nih.gov/pubmed/27208893 | https://www.ncbi.nlm.nih.gov/pubmed/18816528

Gitogenin was first extracted from the herbs of Agave Americana. This compound was found to be a selective inhibitor of UDP- glucuronosyltransferase 1A4 and α-glucosidase, and does not exhibit any inhibition of the major human CYP isoforms. In vitro experiments revealed that gitogenin moderated stimulation for the release of growth hormone from rat pituitary cells.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
UDP-glucuronosyltransferase 1-4 2 Target ID: P22310 Gene ID: 54657.0 Gene Symbol: UGT1A4 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/27208893	Inhibitor 8504
Maltase-glucoamylase, intestinal 1 Target ID: O43451 Gene ID: 8972.0 Gene Symbol: MGAM Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/24530871	Inhibitor 8504		37.2 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

PubMed

Title	Date	PubMed
Drug interaction study of natural steroids from herbs specifically toward human UDP-glucuronosyltransferase (UGT) 1A4 and their quantitative structure activity relationship (QSAR) analysis for prediction.	2016-08	27208893
Longipetalosides A-C, new steroidal saponins from Tribulus longipetalus.	2014-05	24530871
A gas-liquid chromatographic determination of the ratio of gitogenin and digitogenin in mixtures.	1971-01-20	5545780
[Presence of chlorogenin beside the diosgenin and gitogenin in Tribulus terrestris L].	1968	5757749
The baljet reaction and pharmacodynamic studies of diginin and gitogenin.	1948-03	18859483
Digitalis VI, pharmacodynamic studies of gitogenin.	1947-10	20270112

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Mon Mar 31 21:46:04 GMT 2025` Edited by `admin` on `Mon Mar 31 21:46:04 GMT 2025`
Record UNII	60ZMY8IH51
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

GITOGENIN

Common Name

English

NSC-147752

Preferred Name

English

SPIROSTAN-2,3-DIOL, (2ALPHA,3BETA,5ALPHA,25R)-

Common Name

English

DIGIN

Common Name

English

5.ALPHA.,25D-SPIROSTAN-2.ALPHA.,3.BETA.-DIOL

Systematic Name

English

2.ALPHA.-HYDROXYTIGOGENIN

Common Name

English

GITOGENIN [MI]

Common Name

English

(25R)-5.ALPHA.-SPIROSTAN-2.ALPHA.,3.BETA.-DIOL

Systematic Name

English

Code System Code Type Description

NSC

147752