Marmesinin
Basic information
- CAS
27497-13-8- Standard SMILES
CC(C)(O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)[C@@H]1Cc2cc3ccc(=O)oc3cc2O1- InChIKey
HXCGUCZXPFBNRD-NEDVQNLSSA-N- Molecular formula
- C20H24O9
- Average molar mass
- 408.4 g/mol
- Monoisotopic mass
- 408.14203234
Overview
Marmesinin is a member of the class of psoralens that is ()-marmesin in which the hydroxy hydrogen is replaced by a beta-D-glucosyl residue. It has a role as an antioxidant, a P450 inhibitor and a plant metabolite. It is a beta-D-glucoside, a member of psoralens and a monosaccharide derivative. It is functionally related to a nodakenetin.
Names & identifiers
- Preferred name
- Marmesinin
- IUPAC
- (2S)-2-[2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropan-2-yl]-2,3-dihydrofuro[3,2-g]chromen-7-one
- English name
- 7H-Furo(3,2-g)(1)benzopyran-7-one, 2-(1-(beta-D-glucopyranosyloxy)-1-m ethylethyl)-2,3-dihydro-, (S)-
- Molecular formula
- C20H24O9
- Molecular weight
- 408.4
Names & synonyms
MarmesininAmmijin495-30-7(-)-Marmesinin1C1VEU88IFCHEBI:132401(S)-2-(1-(beta-D-Glucopyranosyloxy)-1-methylethyl)-2,3-dihydro-7H-furo(3,2-g)(1)benzopyran-7-one7H-Furo(3,2-g)(1)benzopyran-7-one, 2-(1-(beta-D-glucopyranosyloxy)-1-methylethyl)-2,3-dihydro-, (S)-(2S)-2-[2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropan-2-yl]-2,3-dihydrofuro[3,2-g]chromen-7-one(2S)-2-(2-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxypropan-2-yl)-2,3-dihydrofuro(3,2-g)chromen-7-oneRefChem:155910Ammajin
Show more names
IsorapigeninMarmesinin（ Ammajin,Ammijin,Marmesinin,(-)-Marmesinin）(S)-2-[1-(β-D-Glucopyranosyloxy)-1-methylethyl]-2,3-dihydro-7H-furo[3,2-g][1]benzopyran-7-one(2S)-2α-[1-Methyl-1-(β-D-glucopyranosyloxy)ethyl]-2,3-dihydro-7H-furo[3,2-g][1]benzopyran-7-one7H-Furo[3,2-g][1]benzopyran-7-one, 2-[1-(β-D-glucopyranosyloxy)-1-methylethyl]-2,3-dihydro-, (2S)-
Properties
Computed structural properties
- XLogP
- 0.3
- Topological polar surface area
- 135 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 9
- Rotatable bonds
- 4
- Heavy atoms
- 29
- Formal charge
- 0
- Complexity
- 650
Physicochemical properties
- Melting point
- 259 · 259-260 °C (decomp)(Solv: water (7732-18-5))
- Boiling point
- 657.1 · 657.1±55.0 °C(Predicted)
- Density
- 1.51 · 1.51±0.1 g/cm3(Predicted)
- pka
- 12.9 · 12.90±0.70(Predicted)
- form
- Solid
- color
- White to off-white
- InChIKey
- HXCGUCZXPFBNRD-YTLMEVRINA-N
- SMILES
- C1(=O)OC2=CC3O[C@H](C(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)(C)C)CC=3C=C2C=C1 |&1:7,10,12,15,17,19,r|
- FDA UNII
- 1 C1VEU88IF · 1C1VEU88IF
Chemistry & industry
Applications
UsesMarmesinin ((-)-Marmesinin), a natural coumarin, is a biosynthetic precursor of psoralen and linear furanocoumarins. Marmesinin exhibits significant neuroprotective activities against glutamate-induced toxicity[1][2].
Additional notes
DefinitionChEBI: Marmesinin is a member of the class of psoralens that is (-)-marmesin in which the hydroxy hydrogen is replaced by a beta-D-glucosyl residue. It has a role as a plant metabolite, a P450 inhibitor and an antioxidant. It is a beta-D-glucoside, a member of psoralens and a monosaccharide derivative. It is functionally related to a nodakenetin.
Related reactions
0 records
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Compound notes
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