Compound: naringenin
SMILES: O=C1c2c(O[C@@H](C1)c3ccc(O)cc3)cc(O)cc2O
InChIKey: FTVWIRXFELQLPI-ZDUSSCGKSA-N
Synonyms: naringenin, 480-41-1, (S)-Naringenin, salipurpol, (2S)-Naringenin, Naringenine, Salipurol, naringetol, pelargidanon, 5,7,4'-Trihydroxyflavanone, (-)-(2S)-Naringenin, HN5425SBF2, (S)-2,3-Dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one, DTXSID1022392, CHEBI:17846, (2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one, NSC-11855, NSC-34875, CHEBI:50202, BE-14348A, RefChem:6053, DTXCID302392, 207-550-2, (S)-5,7-Dihydroxy-2-(4-hydroxyphenyl)chroman-4-one, Asahina, NARIGENIN, (-)-Naringenin, CCRIS 5839, YSO1, NSC 11855, C15H12O5, CHEMBL9352, AI3-23355, Flavanone, 4',5,7-trihydroxy-, 2,3-Dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one, (2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one, 4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-, (2S)-, 4H-1-Benzopyran-4-one,2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-, (2S)-, (2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-chromen-4-one, (2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)chroman-4-one, MFCD00870553, NSC 34875, SR-01000721771, UNII-HN5425SBF2, s-naringenin, Nari, 2uxu, 4deu, EINECS 207-550-2, pelargidanon 1602, Spectrum_000247, 4eh3, NARINGENIN [MI], Spectrum2_000325, Spectrum3_000567, Spectrum4_000124, Spectrum5_001423, GlyTouCan:G71790GL, 4',5,7-triOH-Flavone, 4',5,7-Trihydroxyflavanon, NARINGENIN, (-)-, SCHEMBL20570, BSPBio_001954, KBioGR_000508, KBioSS_000727, MLS000574861, BIDD:ER0116, DivK1c_000118, SPECTRUM1500746, 5,7,4'-trihydroxy flavanone, SPBio_000329, 4',5, 7-Trihydroxyflavanone, 5,7-Dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-chromen-4-one, orb1304953, SCHEMBL29351357, BDBM23419, HMS500F20, KBio1_000118, KBio2_000727, KBio2_003295, KBio2_005863, KBio3_001454, 4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-, (S)-, NINDS_000118, (2S)-5,7,4'-trihydroxyflavone, AIDS001417, HMS2202M06, (2S)-4',5,7-trihydroxyflavanone, G71790GL, HY-N0100, MSK40170, TNP00287, (S)-2,3-Dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-4-benzopyrone, CCG-38601, EBC-03873, LMPK12140001, Phytochemistry 8: 127 (1969), s2394, AKOS016843490, CS-6421, DB03467, FN72402, FS-4072, SDCCGMLS-0066570.P001, (2S)-4',5,7-trihydroxyflavan-4-one, IDI1_000118, NCGC00016457-01, NCGC00016457-02, NCGC00016457-03, NCGC00017346-01, NCGC00163598-01, AC-33954, CAS-480-41-1, Flavanone, 4',5,7-trihydroxy- (8CI), SMR000156272, NS00068233, SW219329-1, C00509, EN300-303163, F235652, Q418374, SR-01000721771-3, SR-01000721771-4, 5,7-dihydroxy-2-(4-hydroxyphenyl)-4h-chroman-4-one, BRD-K08832567-001-02-4, BRD-K08832567-001-06-5, BRD-K08832567-001-11-5, (-)-(2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)chroman-4-one, (S)-2,3-dihydo-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one, 2,3-Dihydro-5,6-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one, (2S)-5,7-Dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-1-benzopyran-4-one, 13308-00-4
Theoretical properties:
molecular_formula: C15H12O5
molecular_weight: 272.25 g/mol
exact_mass: 272.06847348 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 3
hydrogen_bond_acceptor_count: 5
rotatable_bond_count: 1
heavy_atom_count: 20
topological_polar_surface_area: 87 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: (S)-naringenin is the (S)-enantiomer of naringenin. It has a role as a plant metabolite and an expectorant. It is a (2S)-flavan-4-one and a naringenin. It is a conjugate acid of a (S)-naringenin(1-). It is an enantiomer of a (R)-naringenin.
chebi: The (<i>S</i>)-enantiomer of naringenin.
chembl: NARINGENIN is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Naringenin is a flavanone from the flavonoid group of polyphenols. It is commonly found in citrus fruits, especially as the predominant flavonone in grapefruit. 
The fate and biological functions of naringenin in vivo are unknown, remaining under preliminary research, as of 2024. High consumption of dietary naringenin is generally regarded as safe, mainly due to its low bioavailability. Taking dietary supplements or consuming grapefruit excessively may impair the action of anticoagulants and increase the toxicity of various prescription drugs. 
Similar to furanocoumarins present in citrus fruits, naringenin may evoke CYP3A4 suppression in the liver and intestines, possibly resulting in adverse interactions with common medications.