1.0 2016-09-30 23:07:54 UTC 2020-05-11 22:30:23 UTC BMDB0004095 BMDB04095 5-Methoxytryptamine 5-Methoxytryptamine, also known as mexamine or 5-meot, belongs to the class of organic compounds known as tryptamines and derivatives. Tryptamines and derivatives are compounds containing the tryptamine backbone, which is structurally characterized by an indole ring substituted at the 3-position by an ethanamine. 5-Methoxytryptamine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. 5-Methoxytryptamine exists in all living organisms, ranging from bacteria to humans. 2-(5-Methoxyindol-3-yl)ethylamine 3-(2-Aminoethyl)-5-methoxyindole 5-MeOT 5-Methoxy-1H-indole-3-ethanamine 5-MT 5MOT Mexamine 2-(5-Methoxy-1H-indol-3-yl)ethanamine 5-Mot Lopac-m-6628 Meksamin Methoxytryptamine Mexamine base Meksamine 5 Methoxytryptamine 5-Methoxytryptamine C11H14N2O 190.2417 190.11061308 2-(5-methoxy-1H-indol-3-yl)ethan-1-amine 5 methoxytryptamine 608-07-1 COC1=CC2=C(NC=C2CCN)C=C1 InChI=1S/C11H14N2O/c1-14-9-2-3-11-10(6-9)8(4-5-12)7-13-11/h2-3,6-7,13H,4-5,12H2,1H3 JTEJPPKMYBDEMY-UHFFFAOYSA-N belongs to the class of organic compounds known as tryptamines and derivatives. Tryptamines and derivatives are compounds containing the tryptamine backbone, which is structurally characterized by an indole ring substituted at the 3-position by an ethanamine. Organic compounds Organoheterocyclic compounds Indoles and derivatives Tryptamines and derivatives Tryptamines and derivatives 2-arylethylamines 3-alkylindoles Alkyl aryl ethers Anisoles Aralkylamines Azacyclic compounds Heteroaromatic compounds Hydrocarbon derivatives Monoalkylamines Organopnictogen compounds Substituted pyrroles 2-arylethylamine 3-alkylindole Alkyl aryl ether Amine Anisole Aralkylamine Aromatic heteropolycyclic compound Azacycle Benzenoid Ether Heteroaromatic compound Hydrocarbon derivative Indole Organic nitrogen compound Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Primary aliphatic amine Primary amine Pyrrole Substituted pyrrole Tryptamine Aromatic heteropolycyclic compounds a small molecule aromatic ether tryptamines Solid melting_point 121.5 °C logp 1.41 ALOGPS logs -2.38 ALOGPS logp 1.33 ChemAxon pka_strongest_acidic 17.45 ChemAxon pka_strongest_basic 9.76 ChemAxon iupac 2-(5-methoxy-1H-indol-3-yl)ethan-1-amine ChemAxon average_mass 190.2417 ChemAxon mono_mass 190.11061308 ChemAxon smiles COC1=CC2=C(NC=C2CCN)C=C1 ChemAxon formula C11H14N2O ChemAxon inchi InChI=1S/C11H14N2O/c1-14-9-2-3-11-10(6-9)8(4-5-12)7-13-11/h2-3,6-7,13H,4-5,12H2,1H3 ChemAxon inchikey JTEJPPKMYBDEMY-UHFFFAOYSA-N ChemAxon polar_surface_area 51.04 ChemAxon refractivity 56.84 ChemAxon polarizability 21.32 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 2 ChemAxon donor_count 2 ChemAxon physiological_charge 1 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 1847 Specdb::CMs 1981 Specdb::CMs 20079 Specdb::CMs 31500 Specdb::CMs 31501 Specdb::CMs 32087 Specdb::CMs 32088 Specdb::CMs 172624 Specdb::NmrTwoD 1925 Specdb::NmrOneD 1990 Specdb::MsIr 2129 Specdb::MsIr 2130 Specdb::MsIr 2131 Specdb::MsMs 2361 Specdb::MsMs 2362 Specdb::MsMs 2363 Specdb::MsMs 5998 Specdb::MsMs 5999 Specdb::MsMs 6000 Specdb::MsMs 6001 Specdb::MsMs 6002 Specdb::MsMs 6003 Specdb::MsMs 6004 Specdb::MsMs 6005 Specdb::MsMs 6006 Specdb::MsMs 6007 Specdb::MsMs 310729 Specdb::MsMs 310730 Specdb::MsMs 310731 Specdb::MsMs 355552 Specdb::MsMs 355553 Specdb::MsMs 355554 Specdb::MsMs 438104 Specdb::MsMs 438105 Specdb::MsMs 438106 Specdb::MsMs 438107 Specdb::MsMs 438108 Specdb::MsMs 439578 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 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 Raw milk, by GC-TOF/MS Sun HZ, Shi K, Wu XH, Xue MY, Wei ZH, Liu JX, Liu HY: Lactation-related metabolic mechanism investigated based on mammary gland metabolomics and 4 biofluids' metabolomics relationships in dairy cows. BMC Genomics. 2017 Dec 2;18(1):936. doi: 10.1186/s12864-017-4314-1. 29197344 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 Ruminal Fluid 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 Thyroid 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 FDB023311 1767 1833 C05659 2089 CPD-12018 5-Methoxytryptamine 7015 Szmuszkovicz, J.; Anthony, W. C.; Heinzelman, R. V. N-Acetyl-5-methoxytryptamine. Journal of Organic Chemistry (1960), 25 857-9. Sun HZ, Shi K, Wu XH, Xue MY, Wei ZH, Liu JX, Liu HY: Lactation-related metabolic mechanism investigated based on mammary gland metabolomics and 4 biofluids' metabolomics relationships in dairy cows. BMC Genomics. 2017 Dec 2;18(1):936. doi: 10.1186/s12864-017-4314-1. 29197344