Compound: Narirutin
SMILES: O=C1c2c(O[C@@H](C1)c3ccc(O)cc3)cc(O[C@@H]4O[C@@H]([C@@H](O)[C@@H]([C@H]4O)O)CO[C@@H]5O[C@H]([C@H](O)[C@H]([C@H]5O)O)C)cc2O
InChIKey: HXTFHSYLYXVTHC-AJHDJQPGSA-N
Synonyms: Narirutin, 14259-46-2, Isonaringenin, Isonaringin, Naringenin 7-O-rutinoside, 06M5EAT0YC, CHEBI:28705, DTXSID30931535, (2S)-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-chromen-7-yl 6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranoside, (2S)-5-hydroxy-2-(4-hydroxyphenyl)-7-[(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]oxy-2,3-dihydrochromen-4-one, 4H-1-benzopyran-4-one, 7-[[6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl]oxy]-2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-, (2S)-, (2S)-5-hydroxy-2-(4-hydroxyphenyl)-7-((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)oxy-2,3-dihydrochromen-4-one, 4H-1-BENZOPYRAN-4-ONE, 7-((6-O-(6-DEOXY-alpha-L-MANNOPYRANOSYL)-beta-D-GLUCOPYRANOSYL)OXY)-2,3-DIHYDRO-5-HYDROXY-2-(4-HYDROXYPHENYL)-, (2S)-, RefChem:43558, DTXCID301360242, 238-138-0, 4H-1-Benzopyran-4-one, 7-((6-O-(6-deoxy-alpa-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-, (2S)-, Naringenin-7-O-rutinoside, (2S)-Narirutin, (S)-5-hydroxy-2-(4-hydroxyphenyl)-7-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-((((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)chroman-4-one, MFCD00017316, 4H-1-Benzopyran-4-one,7-[[6-O-(6-deoxy-a-L-mannopyranosyl)-b-D-glucopyranosyl]oxy]-2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-, (2S)-, (2S)-5-hydroxy-2-(4-hydroxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-3,4-dihydro-2H-1-benzopyran-4-one, Naringenin 7-beta-rutinoside, FEMA No. 2769, EINECS 238-138-0, Narirutin (Standard), Naringenin-7-rutinoside, UNII-06M5EAT0YC, ISONARINGIN [USP-RS], SCHEMBL669946, CHEMBL446246, orb1302282, orb3140930, Narirutin, >=98% (HPLC), SCHEMBL29358529, HY-N0804R, HXTFHSYLYXVTHC-AJHDJQPGSA-N, HY-N0804, MSK40165, BDBM50249471, s9242, NARINGENIN 7.BETA.-RUTINOSIDE, AKOS030530132, CCG-270129, EBC-616393, FN65606, AS-75180, CS-0009810, NS00053810, C09793, F813794, Flavanone, 4',5,7-trihydroxy-, 7-beta-rutinoside, Q13569061, FLAVANONE, 4',5,7-TRIHYDROXY-, 7.BETA.-RUTINOSIDE, (2S)-5-Hydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-7-yl 6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranoside, (2S)-5-hydroxy-2-(4-hydroxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-chroman-4-one, (2S)-7-((6-O-(6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)-.BETA.-D-GLUCOPYRANOSYL)OXY)-2,3-DIHYDRO-5-HYDROXY-2-(4-HYDROXYPHENYL)-4H-1-BENZOPYRAN-4-ONE, (S)-7-((6-O-(6-Deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one, 4H-1-BENZOPYRAN-4-ONE, 7-((6-O-(6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)-.BETA.-D-GLUCOPYRANOSYL)OXY)-2,3-DIHYDRO-5-HYDROXY-2-(4-HYDROXYPHENYL)-, (2S)-, 4H-1-Benzopyran-4-one, 7-((6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranoxyl)oxy)-2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-, (S)-
Theoretical properties:
molecular_formula: C27H32O14
molecular_weight: 580.5 g/mol
exact_mass: 580.17920569 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 8
hydrogen_bond_acceptor_count: 14
rotatable_bond_count: 6
heavy_atom_count: 41
topological_polar_surface_area: 225 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Narirutin is a disaccharide derivative that is (S)-naringenin substituted by a 6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage. It has a role as an antioxidant, a metabolite and an anti-inflammatory agent. It is a member of 4'-hydroxyflavanones, a (2S)-flavan-4-one, a rutinoside, a dihydroxyflavanone and a disaccharide derivative. It is functionally related to a (S)-naringenin.
chebi: A disaccharide derivative that is (<i>S</i>)-naringenin substituted by a 6-<em>O</em>-(6-deoxy-α-<small>L</small>-mannopyranosyl)-β-<small>D</small>-glucopyranosyl moiety at position 7 via a glycosidic linkage.
chembl: NARIRUTIN is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Narirutin is a flavanone-7-O-glycoside, consisting of the flavanone naringenin bonded with the disaccharide rutinose.
It is found in orange juice.
Narirutin is found in citrus fruits such as Yuzu, grapefruit, mandarins, especially in their peels. There are reports that Narirutin is abundant in Jabara(A fruit discovered and grown in the Kitayama village, Wakayama prefecture, Japan).
Narirutin is reported to be effective for allergies caused by immunoglobulin E antibodies. Those allergies include hayfever and some cases of food allergy.

When an allergen (pollen, dust) enters the body, the body produces immunoglobulin E antibodies, resulting in an antigen-antibody reaction.
The antibodies are attached to mast cells, which release bioactive substances such as histamine and serotonin.
Histamine causes expansion of blood vessels, resulting in allergic reactions such as low blood pressure, increased heart rate, skin itchiness, sneezing, runny nose, etc.
Narirutin is said to prevent the release of histamine by the mast cells, reducing the allergic symptoms.