Rutin is a citrus flavonoid glycoside that acts as a potent inhibitor of MAO-B with an IC50 of 4 µM.[1] Because of it's extremely low lipid solubility (it has an XLogP3-AA of -1.3) it cannot cross the blood brain barrier in sufficient quantities to inhibit MAO-B in the brain limiting it's effectiveness to the digestive system and other locations outside of the brain.
Chemical Properties
PubChem Compound ID: 5280805
Molecular Weight: 610.5175 [g/mol]
Molecular Formula: C27H30O16
XLogP3-AA: -1.3
H-Bond Donor: 10
H-Bond Acceptor: 16
IUPAC Name: 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,3R,4S,5S,6R)-3,4,
5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,
5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
InChI: InChI=1S/C27H30O16/c1-8-17(32)20(35)22(37)26(40-8)39-7-15-18(33)21(36)23(38)27(42-15)43-25-19(34)16-13(31)5-10(28)6-14(16)41-24(25)9-2-3-11(29)12(30)4-9/h2-6,8,15,17-18,20-23,26-33,35-38H,7H2,1H3/t8-,15+,17-,18+,20+,21-,22+,23+,26+,27-/m0/s1
InChIKey: IKGXIBQEEMLURG-NVPNHPEKSA-N
Canonical SMILES: CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC(=C(C=C5)O)O)O)O)O)O)O)O
Isomeric SMILES: C[C@H]1[CH]([C@H]([C@H]([CH](O1)OC[CH]2[C@H]([CH]([C@H]([C@@H](O2)OC3=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC(=C(C=C5)O)O)O)O)O)O)O)O