1.0 2016-09-30 23:08:32 UTC 2020-05-11 20:45:39 UTC BMDB0004215 BMDB04215 3,3',4'5-Tetrahydroxystilbene Piceatannol, also known as RSVL-1 or astringinin, belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. Thus, piceatannol is considered to be an aromatic polyketide lipid molecule. Piceatannol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Piceatannol exists in all living species, ranging from bacteria to humans. 3,5,3',4'-Tetrahydroxystilbene 3-Hydroxyresveratol 4-[(e)-2-(3,5-Dihydroxyphenyl)vinyl]benzene-1,2-diol 3,4,3',5'-Tetrahydroxy-trans-stilbene 3,3',4',5-Tetrahydroxystilbene 3,3',4,5'-Tetrahydroxy stilbene RSVL-1 3'-Hydroxyresveratol 3,3',4,5'-Tetrahydroxystilbene 3,5,3',4'-Tetrahydroxy-trans-stilbene Astringinin Demethyl isorhapontigenin Piceatanol 3,5,3',4'-Tetrahydroxy-stilbene Piceatannol 3,3',4'5-Tetrahydroxystilbene (E)-3,3',4,5'-Stilbenetetrol (E)-3,3’,4,5’-Stilbenetetrol 4-[(1E)-2-(3,5-Dihydroxyphenyl)ethenyl]-1,2-benzenediol (E)-Piceatannol Astringenin trans-3,3',4,5'-Tetrahydroxystilbene trans-3,3’,4,5’-Tetrahydroxystilbene trans-Piceatannol C14H12O4 244.246 244.073558866 4-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,2-diol 4-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,2-diol 10083-24-6 OC1=CC(\C=C\C2=CC(O)=C(O)C=C2)=CC(O)=C1 InChI=1S/C14H12O4/c15-11-5-10(6-12(16)8-11)2-1-9-3-4-13(17)14(18)7-9/h1-8,15-18H/b2-1+ CDRPUGZCRXZLFL-OWOJBTEDSA-N belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. Organic compounds Phenylpropanoids and polyketides Stilbenes Stilbenes 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Catechols Hydrocarbon derivatives Organooxygen compounds Resorcinols Styrenes 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid Aromatic homomonocyclic compound Benzenoid Catechol Hydrocarbon derivative Monocyclic benzene moiety Organic oxygen compound Organooxygen compound Phenol Resorcinol Stilbene Styrene Aromatic homomonocyclic compounds Diphenyl ethers, biphenyls, dibenzyls and stilbenes Diphenyl ethers, biphenyls, dibenzyls and stilbenes Stilbenes stilbenol Solid logp 2.12 ALOGPS logs -3.40 ALOGPS logp 3.1 ChemAxon pka_strongest_acidic 8.41 ChemAxon pka_strongest_basic -6.2 ChemAxon iupac 4-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,2-diol ChemAxon average_mass 244.246 ChemAxon mono_mass 244.073558866 ChemAxon smiles OC1=CC(\C=C\C2=CC(O)=C(O)C=C2)=CC(O)=C1 ChemAxon formula C14H12O4 ChemAxon inchi InChI=1S/C14H12O4/c15-11-5-10(6-12(16)8-11)2-1-9-3-4-13(17)14(18)7-9/h1-8,15-18H/b2-1+ ChemAxon inchikey CDRPUGZCRXZLFL-OWOJBTEDSA-N ChemAxon polar_surface_area 80.92 ChemAxon refractivity 69.44 ChemAxon polarizability 25.46 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 4 ChemAxon donor_count 4 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Specdb::CMs 2010 Specdb::CMs 2164 Specdb::CMs 3353 Specdb::CMs 31513 Specdb::CMs 31514 Specdb::CMs 38731 Specdb::CMs 132606 Specdb::CMs 140340 Specdb::MsMs 179991 Specdb::MsMs 179992 Specdb::MsMs 179993 Specdb::MsMs 182325 Specdb::MsMs 182326 Specdb::MsMs 182327 Specdb::MsMs 2241952 Specdb::MsMs 2754007 Specdb::MsMs 2754008 Specdb::MsMs 2754009 Specdb::MsMs 2951262 Specdb::MsMs 2951263 Specdb::MsMs 2951264 Liver 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under corn stover based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Liver 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under alfalfa hay based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Mammary Gland 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under corn stover based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Mammary Gland 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under alfalfa hay based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Milk Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. 23438684 Placenta 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 Platelet 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 581006 DB08399 FDB023335 C05901 667639 PIT 28814 582 C00002895 Piceatannol Bajaj, Renu; Gill, Mark T.; McLaughlin, Jerry L. Improved preparative synthesis of piceatannol (3,4,3',5'-tetrahydroxy-trans-stilbene). Revista Latinoamericana de Quimica (1987), 18(2), 79-80. Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. 23438684