Structure Database (LMSD)

Common Name
Ruscogenin
Systematic Name
(25R)-spirost-5-en-1β,3β-diol
Synonyms
LM ID
LMST01080038
Formula
Exact Mass
Calculate m/z
430.30831
Sum Composition
Status
Curated


Classification

Biological Context

Ruscogenin is a steroid sapogenin that has been found in O. japonicus with diverse biological activities.1,2,3,4,5 It reduces adhesion of HL-60 cells to ECV304 cells induced by phorbol 12-myristate 13-acetate (PMA) with an IC50 value of 7.76 nM and decreases peritoneal leukocyte migration induced by zymosan A in mice when administered at a dose of 5 mg/kg.1 Oral administration of ruscogenin (12.5 mg/kg) inhibits ADP-induced platelet aggregation in rats.2 Ruscogenin prevents monocrotaline-induced increases in mean arterial pressure (MAP), expression of IL-1β and TNF in plasma and lung, and endothelial cell apoptosis in pulmonary arterioles in a rat model of pulmonary hypertension.3 It also reduces proteinuria and renal macrophage infiltration in a rat model of diabetes induced by streptozotocin and decreases gene expression of inflammatory cytokines, dyslipidemia, and liver steatosis in a hamster model of high-fat diet-induced nonalcoholic steatohepatitis (NASH).4,5

This information has been provided by Cayman Chemical

References

1. Lu, H.-J., Tzeng, T.-F., Liou, S.-S., et al. Ruscogenin ameliorates experimental nonalcoholic steatohepatitis via suppressing lipogenesis and inflammatory pathway. Biomed. Res. Int. 652680 (2014).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Ophiopogon japonicus (#100506)
Magnoliopsida (#3398)
Steroid saponins,
Phytochemistry, 1982

String Representations

InChiKey (Click to copy)
QMQIQBOGXYYATH-IDABPMKMSA-N
InChi (Click to copy)
InChI=1S/C27H42O4/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/h5,15-16,18-24,28-29H,6-14H2,1-4H3/t15-,16+,18-,19-,20+,21+,22+,23-,24+,25+,26+,27-/m1/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)CC[C@@H](C)CO6)C)[C@@H]1O

Other Databases

KEGG ID
CHEBI ID
PubChem CID
Cayman ID

Calculated Physicochemical Properties

Heavy Atoms 31
Rings 6
Aromatic Rings 0
Rotatable Bonds 0
Van der Waals Molecular Volume 434.02
Topological Polar Surface Area 63.06
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 4
logP 6.12
Molar Refractivity 121.63

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Updated at
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