1.0 2016-09-30 22:19:14 UTC 2020-05-21 16:28:47 UTC BMDB0000068 BMDB00068 Epinephrine Epinephrinee, also known as epinephrinee or epinephrine, belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety. Epinephrinee exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Epinephrinee exists in all living organisms, ranging from bacteria to humans. Epinephrinee participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and epinephrinee can be biosynthesized from S-adenosylmethionine and norepinephrinee through its interaction with the enzyme phenylethanolamine N-methyltransferase. In addition, Epinephrinee can be converted into 3,4-dihydroxymandelaldehyde and methylamine; which is catalyzed by the enzyme amine oxidase [flavin-containing] a. In cattle, epinephrinee is involved in the metabolic pathway called the tyrosine metabolism pathway. (-)-(R)-Epinephrine (-)-3,4-Dihydroxy-alpha-((methylamino)methyl)benzyl alcohol (-)-Adrenaline (R)-(-)-Adrenaline (R)-(-)-Adnephrine (R)-(-)-Epinephrine (R)-(-)-Epirenamine 4-[(1R)-1-Hydroxy-2-(methylamino)ethyl]-1,2-benzenediol Adrenalin Adrenaline Epinefrina Epinephrin Epinephrinum Epipen Epipen JR L-Adrenaline Levoepinephrine Primatene Auvi-Q (-)-3,4-Dihydroxy-a-((methylamino)methyl)benzyl alcohol (-)-3,4-Dihydroxy-α-((methylamino)methyl)benzyl alcohol (-)-3,4-Dihydroxy-a-[(methylamino)methyl]-benzyl alcohol (-)-3,4-Dihydroxy-a-[2-(methylamino)ethyl]benzyl alcohol (-)-3,4-Dihydroxy-alpha-[(methylamino)methyl]-benzyl alcohol (-)-3,4-Dihydroxy-alpha-[2-(methylamino)ethyl]benzyl alcohol (-)-Epinephrine (R)-4-[1-Hydroxy-2-(methylamino)ethyl]-1,2-benzenediol (R)-Adrenaline (R)-Epinephrine Adnephrine Adrenal Adrenine Adrin Ana-kit Bosmin Bronkaid mist Chelafrin Epifrin Epiglaufrin Epinephran Epirenan Eppy Exadrin Glauposine Hemisine Hemostasin Hemostatin Hypernephrin Isoptoepinal L-1-(3,4-Dihydroxyphenyl)-2-methylaminoethanol L-Epinephrine L-Epirenamine L-Methylaminoethanolcatechol Levorenen Levorenin Levorenine Levoreninum Lyodrin Methylarterenol Mucidrina Nephridine Nieraline Paranephrin Primatene mist R-(-)-Epinephrine Renaglandin Renaleptine Renalina Renoform Renostypticin Renostyptin Scurenaline Simplene Styptirenal Supracapsulin Supranephrane Suprarenaline Suprarenin Surrenine Sus-phrine Takamina Vasoconstrictine Vasotonin 4-(1-Hydroxy-2-(methylamino)ethyl)-1,2-benzenediol Epinephrine bitartrate Epinephrine hydrogen tartrate Lyophrin Adrenaline bitartrate Adrenaline hydrochloride Epinephrine acetate Allergan brand OF adrenaline hydrochloride Epitrate Acetate, epinephrine Adrenaline acid tartrate Epinephrine hydrochloride Medihaler-epi C9H13NO3 183.2044 183.089543287 4-[(1R)-1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol epinephrine 51-43-4 CNC[C@H](O)C1=CC(O)=C(O)C=C1 InChI=1S/C9H13NO3/c1-10-5-9(13)6-2-3-7(11)8(12)4-6/h2-4,9-13H,5H2,1H3/t9-/m0/s1 UCTWMZQNUQWSLP-VIFPVBQESA-N belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety. Organic compounds Benzenoids Phenols Benzenediols Catechols 1,2-aminoalcohols 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Aralkylamines Aromatic alcohols Benzene and substituted derivatives Dialkylamines Hydrocarbon derivatives Organopnictogen compounds Secondary alcohols 1,2-aminoalcohol 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid Alcohol Amine Aralkylamine Aromatic alcohol Aromatic homomonocyclic compound Catechol Hydrocarbon derivative Monocyclic benzene moiety Organic nitrogen compound Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Secondary alcohol Secondary aliphatic amine Secondary amine Aromatic homomonocyclic compounds Adrenalines Biogenic amines adrenaline Solid melting_point 211.5 °C water_solubility 0.18 mg/mL logp -1.37 HANSCH,C & LEO,AJ (1985) logp -0.82 ALOGPS logs -0.99 ALOGPS logp -0.43 ChemAxon pka_strongest_acidic 9.69 ChemAxon pka_strongest_basic 8.91 ChemAxon iupac 4-[(1R)-1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol ChemAxon average_mass 183.2044 ChemAxon mono_mass 183.089543287 ChemAxon smiles CNC[C@H](O)C1=CC(O)=C(O)C=C1 ChemAxon formula C9H13NO3 ChemAxon inchi InChI=1S/C9H13NO3/c1-10-5-9(13)6-2-3-7(11)8(12)4-6/h2-4,9-13H,5H2,1H3/t9-/m0/s1 ChemAxon inchikey UCTWMZQNUQWSLP-VIFPVBQESA-N ChemAxon polar_surface_area 72.72 ChemAxon refractivity 49.23 ChemAxon polarizability 19.04 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 4 ChemAxon donor_count 4 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Tyrosine Metabolism SMP0087235 Specdb::MsIr 141 Specdb::MsIr 142 Specdb::MsIr 143 Specdb::NmrTwoD 1124 Specdb::MsMs 108 Specdb::MsMs 109 Specdb::MsMs 110 Specdb::MsMs 2739 Specdb::MsMs 2740 Specdb::MsMs 2741 Specdb::MsMs 2742 Specdb::MsMs 2743 Specdb::MsMs 2744 Specdb::MsMs 2745 Specdb::MsMs 2746 Specdb::MsMs 2747 Specdb::MsMs 2748 Specdb::MsMs 2749 Specdb::MsMs 2750 Specdb::MsMs 2751 Specdb::MsMs 2752 Specdb::MsMs 2753 Specdb::MsMs 257829 Specdb::MsMs 257830 Specdb::MsMs 257831 Specdb::MsMs 277767 Specdb::MsMs 277768 Specdb::MsMs 277769 Specdb::MsMs 436640 Specdb::CMs 308 Specdb::CMs 8108 Specdb::CMs 30537 Specdb::CMs 37278 Specdb::CMs 171963 Specdb::CMs 1049530 Specdb::CMs 1049532 Specdb::CMs 1049534 Specdb::CMs 1049536 Specdb::CMs 1049537 Specdb::CMs 1049539 Specdb::CMs 1049540 Specdb::CMs 1049542 Specdb::CMs 1049544 Specdb::CMs 1049546 Specdb::CMs 1049548 Specdb::CMs 1049549 Specdb::CMs 1049551 Specdb::CMs 1049553 Specdb::CMs 1049555 Specdb::CMs 1049557 Specdb::CMs 1049559 Specdb::CMs 1049560 Specdb::CMs 1049562 Specdb::CMs 1049564 Specdb::NmrOneD 1066 Specdb::NmrOneD 5532 Specdb::NmrOneD 5533 Specdb::NmrOneD 5534 Specdb::NmrOneD 5535 Specdb::NmrOneD 5536 Specdb::NmrOneD 5537 Specdb::NmrOneD 5538 Specdb::NmrOneD 5539 Specdb::NmrOneD 5540 Specdb::NmrOneD 5541 Specdb::NmrOneD 5542 Specdb::NmrOneD 5543 Specdb::NmrOneD 5544 Specdb::NmrOneD 5545 Specdb::NmrOneD 5546 Specdb::NmrOneD 5547 Specdb::NmrOneD 5548 Specdb::NmrOneD 5549 Specdb::NmrOneD 5550 Specdb::NmrOneD 5551 Adipose Tissue 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 Adrenal Cortex 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 Adrenal Gland 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 Adrenal Medulla 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 Bladder 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 Epidermis 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 Eye Lens 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 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 Intestine 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 Kidney 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 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 Neuron 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 Ovary 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 Pancreas 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 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 Skeletal Muscle 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 Testis 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 C00788 DB00668 FDB021889 5611 5816 28918 C00029643 35997 Epinephrine 5127 L-EPINEPHRINE Singer, Robert A.; Carreira, Erick M. An in situ procedure for catalytic, enantioselective acetate aldol addition. Application to the synthesis of (R)-(-)-epinephrine. Tetrahedron Letters (1997), 38(6), 927-930. BMDBP00010 Cytochrome P450 11B1, mitochondrial P15150 CYP11B1 Enzyme BMDBP00053 Cholesterol side-chain cleavage enzyme, mitochondrial P00189 CYP11A1 Enzyme BMDBP00100 Phenylethanolamine N-methyltransferase P10938 PNMT Enzyme BMDBP00421 Catechol O-methyltransferase A7MBI7 COMT Enzyme BMDBP00890 Amine oxidase [flavin-containing] A P21398 MAOA Enzyme BMDBP01608 Prostaglandin E2 receptor EP4 subtype Q8MJ08 PTGER4 Enzyme BMDBP01816 Pituitary adenylate cyclase-activating polypeptide type I receptor Q29627 ADCYAP1R1 Enzyme BMDBP02578 Beta-2 adrenergic receptor Q28044 ADRB2 Enzyme BMDBP02579 Beta-1 adrenergic receptor Q9TT96 ADRB1 Enzyme BMDBP02675 Steroidogenic factor 1 Q04752 NR5A1 Enzyme