1.0 2016-09-30 23:01:13 UTC 2020-06-04 19:12:35 UTC BMDB0002670 BMDB02670 Naringenin Naringenin, also known as (2S)-naringenin or naringetol, belongs to the class of organic compounds known as flavanones. Flavanones are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3. Thus, naringenin is considered to be a flavonoid lipid molecule. Naringenin exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Naringenin exists in all living organisms, ranging from bacteria to humans. (-)-(2S)-Naringenin (2S)-Naringenin (S)-2,3-Dihydo-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one 4',5,7-Trihydroxyflavanone Naringetol Pelargidanon Salipurpol (-)-Naringenin Asahina Naringenine Salipurol (2S)-2,3-Dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one (2S)-4',5,7-Trihydroxyflavanone (2S)-4’,5,7-Trihydroxyflavanone (S)-Naringenin S-Dihydrogenistein 5,7,4'-Trihydroxyflavanone 5,7,4’-Trihydroxyflavanone C15H12O5 272.2528 272.068473494 (2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one naringenin 480-41-1 [H][C@]1(CC(=O)C2=C(O1)C=C(O)C=C2O)C1=CC=C(O)C=C1 InChI=1S/C15H12O5/c16-9-3-1-8(2-4-9)13-7-12(19)15-11(18)5-10(17)6-14(15)20-13/h1-6,13,16-18H,7H2/t13-/m0/s1 FTVWIRXFELQLPI-ZDUSSCGKSA-N belongs to the class of organic compounds known as flavanones. Flavanones are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3. Organic compounds Phenylpropanoids and polyketides Flavonoids Flavans Flavanones 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids 4'-hydroxyflavonoids 5-hydroxyflavonoids 7-hydroxyflavonoids Alkyl aryl ethers Aryl alkyl ketones Benzene and substituted derivatives Chromones Hydrocarbon derivatives Organic oxides Oxacyclic compounds Vinylogous acids 1-benzopyran 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid 4'-hydroxyflavonoid 5-hydroxyflavonoid 7-hydroxyflavonoid Alkyl aryl ether Aromatic heteropolycyclic compound Aryl alkyl ketone Aryl ketone Benzenoid Benzopyran Chromane Chromone Ether Flavanone Hydrocarbon derivative Hydroxyflavonoid Ketone Monocyclic benzene moiety Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Phenol Vinylogous acid Aromatic heteropolycyclic compounds Flavanones flavanones naringenin Solid melting_point 251 °C logp 2.52 PERRISSOUD,D & TESTA,B (1986) logp 2.47 ALOGPS logs -3.11 ALOGPS logp 2.84 ChemAxon pka_strongest_acidic 7.86 ChemAxon pka_strongest_basic -5 ChemAxon iupac (2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one ChemAxon average_mass 272.2528 ChemAxon mono_mass 272.068473494 ChemAxon smiles [H][C@]1(CC(=O)C2=C(O1)C=C(O)C=C2O)C1=CC=C(O)C=C1 ChemAxon formula C15H12O5 ChemAxon inchi InChI=1S/C15H12O5/c16-9-3-1-8(2-4-9)13-7-12(19)15-11(18)5-10(17)6-14(15)20-13/h1-6,13,16-18H,7H2/t13-/m0/s1 ChemAxon inchikey FTVWIRXFELQLPI-ZDUSSCGKSA-N ChemAxon polar_surface_area 86.99 ChemAxon refractivity 71.29 ChemAxon polarizability 27.31 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 5 ChemAxon donor_count 3 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Specdb::NmrTwoD 1835 Specdb::CMs 821 Specdb::CMs 822 Specdb::CMs 7854 Specdb::CMs 30641 Specdb::CMs 30642 Specdb::CMs 31942 Specdb::CMs 31943 Specdb::CMs 31944 Specdb::CMs 38458 Specdb::CMs 137101 Specdb::CMs 144835 Specdb::MsMs 2122 Specdb::MsMs 2123 Specdb::MsMs 2124 Specdb::MsMs 5788 Specdb::MsMs 5789 Specdb::MsMs 5790 Specdb::MsMs 5791 Specdb::MsMs 5792 Specdb::MsMs 5793 Specdb::MsMs 256323 Specdb::MsMs 256324 Specdb::MsMs 256325 Specdb::MsMs 276264 Specdb::MsMs 276265 Specdb::MsMs 276266 Specdb::MsMs 285561 Specdb::MsMs 285562 Specdb::MsMs 285563 Specdb::MsMs 285564 Specdb::MsMs 285565 Specdb::MsMs 285566 Specdb::MsMs 285567 Specdb::MsMs 373627 Specdb::MsMs 373628 Specdb::MsMs 373629 Specdb::NmrOneD 1899 Specdb::NmrOneD 293255 Specdb::NmrOneD 293256 Specdb::NmrOneD 293257 Specdb::NmrOneD 293258 Specdb::NmrOneD 293259 Specdb::NmrOneD 293260 Specdb::NmrOneD 293261 Specdb::NmrOneD 293262 Specdb::NmrOneD 293263 Specdb::NmrOneD 293264 Specdb::NmrOneD 293265 Specdb::NmrOneD 293266 Specdb::NmrOneD 293267 Specdb::NmrOneD 293268 Specdb::NmrOneD 293269 Specdb::NmrOneD 293270 Specdb::NmrOneD 293271 Specdb::NmrOneD 293272 Specdb::NmrOneD 293273 Specdb::NmrOneD 293274 Blood Samples collected from 16 multiparous Holstein cows Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28. 25599412 Fibroblasts Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Liver Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Milk 0.0492 - 0.0606 uM Raw milk, range from both high equol and low equol milk - high = diet of mainly red clover Nielsen TS, Norgaard JV, Purup S, Frette XC, Bonefeld-Jorgensen EC: Estrogenic activity of bovine milk high or low in equol using immature mouse uterotrophic responses and an estrogen receptor transactivation assay. Cancer Epidemiol. 2009 Jul;33(1):61-8. doi: 10.1016/j.canep.2009.04.003. Epub 2009 May 31. 19679050 DB03467 FDB000678 C00509 388383 439246 17846 201 NARINGENIN-CMPD C00000982 Naringenin 3401 Nielsen TS, Norgaard JV, Purup S, Frette XC, Bonefeld-Jorgensen EC: Estrogenic activity of bovine milk high or low in equol using immature mouse uterotrophic responses and an estrogen receptor transactivation assay. Cancer Epidemiol. 2009 Jul;33(1):61-8. doi: 10.1016/j.canep.2009.04.003. Epub 2009 May 31. 19679050