1.0 2011-09-21 00:28:35 UTC 2015-07-21 06:57:39 UTC FDB023355 Acetyl-N-formyl-5-methoxykynurenamine Acetyl-N-formyl-5-methoxykynurenamine (AFMK) results from the oxidative cleavage of the pyrrole ring during melatonin oxidation by myeloperoxidase (MPO), a superoxide anion (O)-dependent reaction. AFMK is also expected to be formed from oxidation catalyzed by the unspecific enzyme indoleamine-2,3-dioxygenase (IDO), found in a variety of cell types including monocyte/macrophage lineages. MPO- and IDO-catalyzed melatonin oxidation has the requirement of O in common, a species formed in large amounts in inflammatory conditions. The non-enzymatic formation of AFMK can also be expected by its direct reaction with highly reactive oxygen species, such as hydroxyl radical and singlet oxygen. Thus, we assume that AFMK is a product formed in a route of melatonin metabolism, especially active in inflammation. As AFMK is biologically more active on leukocytes than melatonin, the metabolizing of melatonin to AFMK at inflammatory sites possibly plays a role in immunomodulation. AFMK is found in the CSF of patients with meningitis, and in some samples at a remarkably high concentration, with AFMK found in some patients exceeding the concentration of melatonin normally found in serum. (PMID: 16150112) [HMDB] AFMK Formyl-N-acetyl-5-methoxykynurenamine N-[3-(2-formamido-5-methoxy-phenyl)-3-oxo-propyl]acetamide N-Acetyl-N-formyl-5-methoxykynurenamine C13H16N2O4 264.2771 264.11100701 N-[3-(2-formamido-5-methoxyphenyl)-3-oxopropyl]acetamide N-[3-(2-formamido-5-methoxyphenyl)-3-oxopropyl]acetamide 52450-38-1 COC1=CC(C(=O)CCNC(C)=O)=C(NC=O)C=C1 InChI=1S/C13H16N2O4/c1-9(17)14-6-5-13(18)11-7-10(19-2)3-4-12(11)15-8-16/h3-4,7-8H,5-6H2,1-2H3,(H,14,17)(H,15,16) JYWNYMJKURVPFH-UHFFFAOYSA-N belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. Alkyl-phenylketones Organic compounds Organic oxygen compounds Organooxygen compounds Carbonyl compounds Aromatic homomonocyclic compounds Acetamides Alkyl aryl ethers Anilides Anisoles Aryl alkyl ketones Benzoyl derivatives Hydrocarbon derivatives Methoxyanilines Methoxybenzenes N-arylamides Organic oxides Organopnictogen compounds Phenoxy compounds Secondary carboxylic acid amides Vinylogous amides Acetamide Alkyl aryl ether Alkyl-phenylketone Anilide Anisole Aromatic homomonocyclic compound Aryl alkyl ketone Benzenoid Benzoyl Carboxamide group Carboxylic acid derivative Ether Hydrocarbon derivative Methoxyaniline Methoxybenzene Monocyclic benzene moiety N-arylamide Organic nitrogen compound Organic oxide Organonitrogen compound Organopnictogen compound Phenol ether Phenoxy compound Secondary carboxylic acid amide Vinylogous amide a small molecule kynurenamines Solid logp 0.50 ALOGPS logs -3.19 ALOGPS solubility 1.69e-01 g/l ALOGPS logp 0.34 ChemAxon pka_strongest_acidic 13.9 ChemAxon pka_strongest_basic -1.6 ChemAxon iupac N-[3-(2-formamido-5-methoxyphenyl)-3-oxopropyl]acetamide ChemAxon average_mass 264.2771 ChemAxon mono_mass 264.11100701 ChemAxon smiles COC1=CC(C(=O)CCNC(C)=O)=C(NC=O)C=C1 ChemAxon formula C13H16N2O4 ChemAxon inchi InChI=1S/C13H16N2O4/c1-9(17)14-6-5-13(18)11-7-10(19-2)3-4-12(11)15-8-16/h3-4,7-8H,5-6H2,1-2H3,(H,14,17)(H,15,16) ChemAxon inchikey JYWNYMJKURVPFH-UHFFFAOYSA-N ChemAxon polar_surface_area 84.5 ChemAxon refractivity 70.8 ChemAxon polarizability 27.13 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Tryptophan Metabolism SMP00063 map00380 Specdb::CMs 10181 Specdb::CMs 32334 Specdb::CMs 32335 Specdb::CMs 99845 Specdb::CMs 99846 Specdb::CMs 132757 Specdb::CMs 140491 Specdb::MsMs 288469 Specdb::MsMs 288470 Specdb::MsMs 288471 Specdb::MsMs 327598 Specdb::MsMs 327599 Specdb::MsMs 327600 Specdb::MsMs 2256456 Specdb::MsMs 2258120 Specdb::MsMs 2722149 Specdb::MsMs 2722150 Specdb::MsMs 2722151 Specdb::MsMs 2959647 Specdb::MsMs 2959648 Specdb::MsMs 2959649 HMDB04259 #<Reference:0x000055ce32871b70> Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823