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Structure Database (LMSD)

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Common Name

delta5-Convallamarogenin

Systematic Name

Spirosta-5,25(27)-dien-1β,3β-diol

Synonyms

Neoruscogenin

LM ID

LMST01080048

Formula

C₂₇H₄₀O₄

Exact Mass

Calculate m/z

428.29266

Sum Composition

ST 27:4;O4

Status

Curated

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Classification

Biological Context

Neoruscogenin is a natural sapogenin isolated from Butcher’s broom (R. rhizoma), which is traditionally used against chronic venous disorders.¹ It is a bioavailable, potent, and high-affinity agonist of the nuclear receptor RORα (EC50 = 110 nM).² In mice, neoruscogenin up-regulates the expression of several RORα-inducible genes in the liver, when given at 3 mg/kg/d orally for seven days.²

This information has been provided by Cayman Chemical

References

1. Helleboid, S., Haug, C., Lamottke, K., et al. The identification of naturally occurring neoruscogenin as a bioavailable, potent, and high-affinity agonist of the nuclear receptor RORα (NR1F1). J. Biomol. Screen. 19(3), 399-406 (2014).

2. Barbic, M., Willer, E.A., Rothenhöfer, M., et al. Spirostanol saponins and esculin from Rusci rhizoma reduce the thrombin-induced hyperpermeability of endothelial cells. Phytochemistry 90, 106-113 (2013).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Ruscus aculeatus (#59067)

Magnoliopsida (#3398)

Spirostanol saponins and esculin from Rusci rhizoma reduce the thrombin-induced hyperpermeability of endothelial cells.,
Phytochemistry, 2013

Pubmed ID: 23499166

String Representations

InChiKey (Click to copy)

ALTRINCJVPIQNK-NHIXJPGBSA-N

InChi (Click to copy)

InChI=1S/C27H40O4/c1-15-7-10-27(30-14-15)16(2)24-22(31-27)13-21-19-6-5-17-11-18(28)12-23(29)26(17,4)20(19)8-9-25(21,24)3/h5,16,18-24,28-29H,1,6-14H2,2-4H3/t16-,18+,19+,20-,21-,22-,23+,24-,25-,26-,27+/m0/s1

SMILES (Click to copy)

C1[C@H](O)CC2[C@@](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=2)CCC(=C)CO6)C)[C@@H]1O