Rutarin
Basic information
- CAS
20320-81-4- Standard SMILES
CC(C)(O)[C@@H]1Cc2cc3ccc(=O)oc3c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)c2O1- InChIKey
JWWFVRMFYKPZNE-VVIWCBLHSA-N- Molecular formula
- C20H24O10
- Average molar mass
- 424.4 g/mol
- Monoisotopic mass
- 424.13694696
Overview
Rutarin is a monosaccharide derivative that is beta-D-glucopyranose in which the hydroxy group at position 1 is substituted by a [(2S)-2-(2-hydroxypropan-2-yl)-7-oxo-2,3-dihydro-7H-furo[3,2-g][1]benzopyran-9-yl]oxy group. It is a natural product found in several plant species including Ruta graveolens and Citropsis articulata. It has a role as an antibacterial agent, an antiplasmodial drug and a plant metabolite. It is a beta-D-glucoside, a member of psoralens and a monosaccharide derivative.
Names & identifiers
- Preferred name
- Rutarin
- IUPAC
- (2S)-2-(2-hydroxypropan-2-yl)-9-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrofuro[3,2-g]chromen-7-one
- English name
- RUTARIN
- Molecular formula
- C20H24O10
- Molecular weight
- 424.4
Names & synonyms
Rutarin20320-81-4CampeseninUNII-NBL6IC1992NBL6IC1992(2S)-2-(2-hydroxypropan-2-yl)-9-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrofuro[3,2-g]chromen-7-oneCHEBI:69039(2S)-2-(2-hydroxypropan-2-yl)-7-oxo-2,3-dihydro-7H-furo[3,2-g][1]benzopyran-9-yl beta-D-glucopyranoside7H-Furo(3,2-g)(1)benzopyran-7-one, 9-(beta-D-glucopyranosyloxy)-2,3-dihydro-2-(1-hydroxy-1-methylethyl)-(2S)-2-(2-hydroxypropan-2-yl)-7-oxo-2,3-dihydro-7H-furo[3,2-g]chromen-9-yl beta-D-glucopyranoside7H-FURO(3,2-G)(1)BENZOPYRAN-7-ONE, 9-(.BETA.-D-GLUCOPYRANOSYLOXY)-2,3-DIHYDRO-2-(1-HYDROXY-1-METHYLETHYL)-, S-(2S)-2-(2-hydroxypropan-2-yl)-7-oxo-2,3-dihydro-7H-furo(3,2-g)(1)benzopyran-9-yl beta-D-glucopyranoside
Show more names
7H-Furo[3,2-g][1]benzopyran-7-one, 9-(β-D-glucopyranosyloxy)-2,3-dihydro-2-(1-hydroxy-1-methylethyl)-
(2S)-2-(2-hydroxypropan-2-yl)-7-oxo-2,3-dihydro-7H-furo(3,2-g)chromen-9-yl beta-D-glucopyranoside(2S)-2-(2-hydroxypropan-2-yl)-9-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy-2,3-dihydrofuro(3,2-g)chromen-7-one9-(beta-D-glucopyranosyloxy)-2,3-dihydro-2-(1-hydroxy-1-methylethyl)-7H-furo(3,2-g)(1)benzopyran-7-one9-(beta-D-glucopyranosyloxy)-2,3-dihydro-2-(1-hydroxy-1-methylethyl)-7H-furo[3,2-g][1]benzopyran-7-oneRefChem:180362(2S)-2-(1-hydroxy-1-methyl-ethyl)-9-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl)oxy-2,3-dihydrofuro(3,2-g)chromen-7-one(2S)-2-(1-hydroxy-1-methyl-ethyl)-9-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-2,3-dihydrofuro[3,2-g]chromen-7-one7H-FURO(3,2-G)(1)BENZOPYRAN-7-ONE, 9-(BETA-D-GLUCOPYRANOSYLOXY)-2,3-DIHYDRO-2-(1-HYDROXY-1-METHYLETHYL)-, S-
Properties
Computed structural properties
- XLogP
- -0.2
- Topological polar surface area
- 155 Ų
- Hydrogen bond donors
- 5
- Hydrogen bond acceptors
- 10
- Rotatable bonds
- 4
- Heavy atoms
- 30
- Formal charge
- 0
- Complexity
- 680
Experimental & physicochemical properties
Endocrine DisruptorsPotential endocrine disrupting compound
Physicochemical properties
- Boiling point
- 726.5 · 726.5±60.0 °C(Predicted)
- Density
- 1.562 · 1.562±0.06 g/cm3(Predicted)
- form
- Solid
- pka
- 12.71 · 12.71±0.70(Predicted)
- color
- White to off-white
- InChIKey
- JWWFVRMFYKPZNE-BLALXGCGNA-N
- SMILES
- C1(=O)OC2=C(C=C3C[C@@H](C(O)(C)C)OC3=C2OC2[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O2)C=C1 |&1:8,18,20,22,24,r|
- FDA UNII
- 6 IC1992 · NBL6IC1992
Chemistry & industry
Applications
UsesRutarin is a Coumarin (HY-N0709) derivative, that can be isolated from the aerial parts of the plant Atalantta racemosa[1].
Additional notes
DefinitionChEBI: A natural product found in Citropsis articulata.
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