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Structure Database (LMSD)

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Common Name

Gitogenin

Systematic Name

(25R)-5α-spirostan-2α,3β-diol

Synonyms

LM ID

LMST01080010

Formula

C₂₇H₄₄O₄

Exact Mass

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432.32396

Sum Composition

ST 27:2;O4

Status

Curated

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Classification

Biological Context

Gitogenin is a sapogenin that has been found in T. foenum-graecum and has enzyme inhibitory and hormone-releasing activities.^1,2 It is an inhibitor of UDP-glucuronosyltransferase (UGT) isoform UGT1A4 (IC50 = 0.69 µM).¹ Gitogenin (20 µg/ml) stimulates the release of growth hormone in primary rat pituitary cells.²

This information has been provided by Cayman Chemical

References

1. Shim, S.H., Lee, E.J., Kim, J.S., et al. Rat growth-hormone release stimulators from fenugreek seeds. Chem. Biodivers. 5(9), 1753-1761 (2008).

2. Xu, M., Dong, P., Tian, X., et al. 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. Pharmacol. Res. 110, 139-150 (2016).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Capsicum annuum (#4072)

Magnoliopsida (#3398)

Steroid saponins,
Phytochemistry, 1982

DOI: 10.1016/S0031-9422(00)82400-0

String Representations

InChiKey (Click to copy)

FWCXELAAYFYCSR-RYKNUXCGSA-N

InChi (Click to copy)

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

SMILES (Click to copy)

C1[C@]2(C)[C@@]3([H])CC[C@]4(C)[C@H]5[C@@H]([C@]6(O[C@H]5C[C@@]4([H])[C@]3([H])CC[C@@]2([H])C[C@@H](O)[C@@H]1O)CC[C@@H](C)CO6)C