Montbretin A
[(2R,3S,4S,5R,6S)-6-[(2S,3R,4R,5R,6S)-2-[2-[4-[(2S,3R,4R,5R)-3,4-dihydroxy-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-3,5-dihydroxyphenyl]-5,7-dihydroxy-4-oxochromen-3-yl]oxy-4,5-dihydroxy-6-methyloxan-3-yl]oxy-3,4-dihydroxy-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
Molecular Identity
Montbretin A
[(2R,3S,4S,5R,6S)-6-[(2S,3R,4R,5R,6S)-2-[2-[4-[(2S,3R,4R,5R)-3,4-dihydroxy-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-3,5-dihydroxyphenyl]-5,7-dihydroxy-4-oxochromen-3-yl]oxy-4,5-dihydroxy-6-methyloxan-3-yl]oxy-3,4-dihydroxy-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
PubChem CID: 138911123
Montbretin A is a glycosyloxyflavone that is myricetin in which the hydroxy groups at the 3 and 4' positions have been glycosylated by an alpha-L-rhamnopyranosyl-(12)-6-O-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-beta-D-glucopyranosyl-(12)-alpha-L-rhamnopyranosyl group and a 4-O-(alpha-L-rhamnopyranosyl)-beta-D-xylopyranose group, respectively. It is functionally related to a myricetin 3-O-[(6-O-caffeoyl-beta-D-glucosyl)-(1->2)-alpha-L-rhamnoside](1-). It is a conjugate acid of a montbretin A(1-).
2D Structure
Properties
C53H64O32
Molecular Formula
1213.10
Molecular Weight
g/mol
1212.3381
Exact Mass
Da
-3.6
XLogP
Drug-like (Lipinski: < 5)
509
TPSA
May have limited oral absorption
18
H-Bond Donors
32
H-Bond Acceptors
2290
Complexity
SMILES
Canonical SMILES
SMILES: CC1C(C(C(C(O1)OC2COC(C(C2O)O)OC3=C(C=C(C=C3O)C4=C(C(=O)C5=C(C=C(C=C5O4)O)O)OC6C(C(C(C(O6)C)O)O)OC7C(C(C(C(O7)COC(=O)C=CC8=CC(=C(C=C8)O)O)O)O)OC9C(C(C(C(O9)C)O)O)O)O)O)O)OIsomeric SMILES
SMILES: C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2CO[C@H]([C@@H]([C@H]2O)O)OC3=C(C=C(C=C3O)C4=C(C(=O)C5=C(C=C(C=C5O4)O)O)O[C@H]6[C@@H]([C@@H]([C@H]([C@@H](O6)C)O)O)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)COC(=O)/C=C/C8=CC(=C(C=C8)O)O)O)O)O[C@H]9[C@@H]([C@@H]([C@H]([C@@H](O9)C)O)O)O)O)O)O)OSynonyms(6)
CHEBI:144419RefChem:926108((3S,6S)-6-((2S,4S,5R)-2-(2-(4-((2S,3R,5R)-3,4-dihydroxy-5-((2S,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl)oxy-3,5-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl)oxy-4,5-dihydroxy-6-methyloxan-3-yl)oxy-3,4-dihydroxy-5-((2S,3R,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxyoxan-2-yl)methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate115712-92-0Montbretin A2-(4-{[4-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-xylopyranosyl]oxy}-3,5-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl 6-deoxy-alpha-L-mannopyranosyl-(1->2)-6-O-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-beta-D-glucopyranosyl-(1->2)-6-deoxy-alpha-L-mannopyranoside
Data from PubChem (NCBI)
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Drug Network
Trials and conditions connected to Montbretin A
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