Structure Database (LMSD)
Common Name
Monotropein
Systematic Name
Synonyms
3D model of Monotropein
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
Level 4 Class
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
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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Created at
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Updated at
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