Structure Database (LMSD)

Common Name
Monotropein
Systematic Name
Synonyms
LM ID
LMPR0102070012
Formula
Exact Mass
Calculate m/z
390.116215
Status
Curated

Classification

Biological Context

Monotropein is an iridoid glycoside originally isolated from M. officinalis roots and has diverse biological activities.1,2,3,4,5 It increases cell viability and migration of bone marrow-derived endothelial progenitor cells (BM-EPCs) when used at concentrations ranging from 0.1 to 1,000 μM.1 Monotropein inhibits apoptosis and reduces levels of matrix metalloproteinase-3 (MMP-3) and MMP-13 in chondrocytes.2 It inhibits LPS-induced nuclear translocation of NF-κB and reduces COX-2, inducible nitric oxide synthase (iNOS), TNF-α, and IL-1β mRNA expression in RAW 264.7 cells.3 Monotropein (100 and 200 mg/kg) reduces colonic myeloperoxidase (MPO) activity, COX-2 and iNOS mRNA expression, and disease severity in a mouse model of ulcerative colitis induced by dextran sulfate sodium (DSS). It increases bone mineral content, bone mineral density, and improves bone microstructure in ovariectomized mice when administered at doses of 40 or 80 mg/kg.4 Monotropein (20 and 30 mg/kg) reduces acetic acid-induced writhing in mice and carrageenan-induced paw edema in rats.5 It also decreases macrophage infiltration and wound healing time and increases blood vessel formation in a rat model of wound healing.1

This information has been provided by Cayman Chemical

References

String Representations

InChiKey (Click to copy)
HPWWQPXTUDMRBI-NJPMDSMTSA-N
InChi (Click to copy)
InChI=1S/C16H22O11/c17-3-8-10(19)11(20)12(21)15(26-8)27-14-9-6(1-2-16(9,24)5-18)7(4-25-14)13(22)23/h1-2,4,6,8-12,14-15,17-21,24H,3,5H2,(H,22,23)/t6-,8-,9-,10-,11+,12-,14+,15+,16+/m1/s1
SMILES (Click to copy)
O([C@@H]1OC=C(C(=O)O)[C@@]2([H])C=C[C@](O)(CO)[C@]21[H])[C@H]1[C@H](O)[C@H]([C@H](O)[C@H](O1)CO)O

Other Databases

KEGG ID
CHEBI ID
PubChem CID
Cayman ID

Calculated Physicochemical Properties

Heavy Atoms 27
Rings 3
Aromatic Rings 0
Rotatable Bonds 5
Van der Waals Molecular Volume 337.05
Topological Polar Surface Area 190.51
Hydrogen Bond Donors 7
Hydrogen Bond Acceptors 11
logP -0.77
Molar Refractivity 88.16

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Updated at
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