Monotropein
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Monotropein
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CAS No:
5945-50-6
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Formula:
C16H22O11
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Chemical Name:
Monotropein
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Synonyms:
Cyclopenta[c]pyran-4-carboxylic acid,1-(β-D-glucopyranosyloxy)-1,4a,7,7a-tetrahydro-7-hydroxy-7-(hydroxymethyl)-,(1S,4aS,7R,7aS)-;Monotropein;Cyclopenta[c]pyran-4-carboxylic acid,1-(β-D-glucopyranosyloxy)-1,4a,7,7a-tetrahydro-7-hydroxy-7-(hydroxymethyl)-,[1S-(1α,4aα,7β,7aα)]-;(1S,4aS,7R,7aS)-1-(β-D-Glucopyranosyloxy)-1,4a,7,7a-tetrahydro-7-hydroxy-7-(hydroxymethyl)cyclopenta[c]pyran-4-carboxylic acid;Monotropeine;NSC 291303;NSC 88926;98845-47-7;1365-63-5;27120-79-2;31018-71-0;741212-56-6
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CAS No:
Description
Monotropein is an iridoid glycoside isolated Morinda officinalis. Monotropein inhibits the expression of inflammatory mediators in dextran sulfate sodium (DSS)-induced colitis mouse model[1].
Monotropein is an iridoid monoterpenoid that is 1,4a,7,7a-tetrahydrocyclopenta[c]pyran substituted by a beta-D-glucopyranosyloxy group at position 1, a carboxylic acid group at position 4, and at position 7 by a hydroxy and hydroxymethyl groups respectively (the 1S,4aS,7R,7aS diastereomer). It has a role as a metabolite and an anti-inflammatory agent. It is a cyclopentapyran, a monocarboxylic acid, an iridoid monoterpenoid, a beta-D-glucoside and a monosaccharide derivative.
Characteristics
186.37000
-4.43
1.7±0.1 g/cm3
170-173 °C
717.6±60.0 °C at 760 mmHg
262.0±26.4 °C
1.686
Monotropein Use and Manufacturing
Lipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C10 isoprenoids (monoterpenes) [PR0102]
Computed Properties
Molecular Weight:390.34
XLogP3:-3.1
Hydrogen Bond Donor Count:7
Hydrogen Bond Acceptor Count:11
Rotatable Bond Count:5
Exact Mass:390.11621151
Monoisotopic Mass:390.11621151
Topological Polar Surface Area:186
Heavy Atom Count:27
Complexity:634
Defined Atom Stereocenter Count:9
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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