naringin   Click here for help

GtoPdb Ligand ID: 4738

Comment: Naringin is the foremost flavonoid in grapefruit and is reported to have a deleterious effect on intestinal drug absorption by inhibiting the transport protein OATP1A2 [1].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 10
Hydrogen bond donors 8
Rotatable bonds 6
Topological polar surface area 225.06
Molecular weight 580.18
XLogP -0.11
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES OCC1OC(Oc2cc(O)c3c(c2)OC(CC3=O)c2ccc(cc2)O)C(C(C1O)O)OC1OC(C)C(C(C1O)O)O
Isomeric SMILES OC[C@H]1O[C@@H](Oc2cc(O)c3c(c2)O[C@@H](CC3=O)c2ccc(cc2)O)[C@@H]([C@H]([C@@H]1O)O)O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O
InChI InChI=1S/C27H32O14/c1-10-20(32)22(34)24(36)26(37-10)41-25-23(35)21(33)18(9-28)40-27(25)38-13-6-14(30)19-15(31)8-16(39-17(19)7-13)11-2-4-12(29)5-3-11/h2-7,10,16,18,20-30,32-36H,8-9H2,1H3/t10-,16-,18+,20-,21+,22+,23-,24+,25+,26-,27+/m0/s1
InChI Key DFPMSGMNTNDNHN-ZPHOTFPESA-N
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Compound class Natural product or derivative
IUPAC Name Click here for help
(2S)-7-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)chroman-4-one
Database Links Click here for help
CAS Registry No. 10236-47-2 (source: Scifinder)
ChEBI CHEBI:28819
ChEMBL Ligand CHEMBL451532
GtoPdb PubChem SID 178101449
PubChem CID 442428
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Wikipedia Naringin