2.02012-07-30 14:54:42 -06002015-06-03 17:20:45 -0600ECMDB21153M2MDB0015622-Aminomalonate semialdehyde2-Aminomalonate semialdehyde is an organic compound that can be formed from a reaction between NADP+ and L-serine. (EcoCyc)(2S)-2-amino-3-oxopropanoate(2S)-2-amino-3-oxopropanoic acid(S)-2-amino-3-oxopropanoate(S)-2-amino-3-oxopropanoic acid2-Amino-3-oxo-Propanoate2-Amino-3-oxo-Propanoic acid2-Amino-3-oxopropionate2-Amino-3-oxopropionic acid2-Aminomalonate semialdehyde2-Aminomalonic acid semialdehyde2-Ammoniomalonate semialdehyde2-Ammoniomalonic acid semialdehyde2-Formylglycine3-Oxo-(9CI)-Alanine3-Oxo-L-alanine3-OxoalanineA-FormylglycineAlpha-FormylglycineAmino-(8CI)MalonaldehydateAmino-(8CI)Malonaldehydic acidL-3-OxoalanineL-a-FormylglycineL-alpha-FormylglycineL-Amino-malonate semialdehydeL-Amino-malonic acid semialdehydeL-AminomalonaldehydateL-Aminomalonaldehydic acidL-Serine semialdehyde [misnomer]L-α-Formylglycineα-FormylglycineC3H5NO3103.0767103.026943031(2S)-2-amino-3-oxopropanoic acid2-aminomalonate semialdehyde5735-66-0N[C@@H](C=O)C(O)=OInChI=1S/C3H5NO3/c4-2(1-5)3(6)7/h1-2H,4H2,(H,6,7)/t2-/m0/s1XMTCKNXTTXDPJX-REOHCLBHSA-NSolidCytosollogp-2.78logs0.37solubility2.42e+02 g/llogp-3.6pka_strongest_acidic1.66pka_strongest_basic7.18iupac(2S)-2-amino-3-oxopropanoic acidaverage_mass103.0767mono_mass103.026943031smilesN[C@@H](C=O)C(O)=OformulaC3H5NO3inchiInChI=1S/C3H5NO3/c4-2(1-5)3(6)7/h1-2H,4H2,(H,6,7)/t2-/m0/s1inchikeyXMTCKNXTTXDPJX-REOHCLBHSA-Npolar_surface_area80.39refractivity21.06polarizability8.51rotatable_bond_count2acceptor_count4donor_count2physiological_charge0formal_charge0Secondary Metabolites: cysteine biosynthesis from serineThe pathway starts with a 3-phosphoglyceric acid interacting with an NAD driven D-3-phosphoglycerate dehydrogenase / α-ketoglutarate reductase resulting in an NADH, a hydrogen ion and a phosphohydroxypyruvic acid. This compound then interacts with an L-glutamic acid through a 3-phosphoserine aminotransferase / phosphohydroxythreonine aminotransferase resulting in a oxoglutaric acid and a DL-D-phosphoserine. The latter compound then interacts with a water molecule through a phosphoserine phosphatase resulting in a phosphate and an L-serine. The L-serine interacts with an acetyl-coa through a serine acetyltransferase resulting in a release of a Coenzyme A and a O-Acetylserine. The O-acetylserine then interacts with a hydrogen sulfide through a O-acetylserine sulfhydrylase A resulting in an acetic acid, a hydrogen ion and an L-cysteinePW000977MetabolicSpecdb::CMs3189Specdb::NmrOneD297695Specdb::NmrOneD297696Specdb::NmrOneD297697Specdb::NmrOneD297698Specdb::NmrOneD297699Specdb::NmrOneD297700Specdb::NmrOneD297701Specdb::NmrOneD297702Specdb::NmrOneD297703Specdb::NmrOneD297704Specdb::NmrOneD297705Specdb::NmrOneD297706Specdb::NmrOneD297707Specdb::NmrOneD297708Specdb::NmrOneD297709Specdb::NmrOneD297710Specdb::NmrOneD297711Specdb::NmrOneD297712Specdb::NmrOneD297713Specdb::NmrOneD297714Specdb::MsMs26519Specdb::MsMs26520Specdb::MsMs26521Specdb::MsMs33077Specdb::MsMs33078Specdb::MsMs33079HMDB1160225244138391645C11822586712-AMINOMALONATE-SEMIALDEHYDENADP-dependent L-serine/L-allo-threonine dehydrogenase ydfGP39831YDFG_ECOLIydfGhttp://ecmdb.ca/proteins/P39831.xmlNADP + L-Serine <> 2-Aminomalonate semialdehyde + Hydrogen ion + NADPHRXN0-2201NADP + D-Serine <> 2-Aminomalonate semialdehyde + Hydrogen ion + NADPHL-Serine + NADP 2-Aminomalonate semialdehyde + NADPH + Hydrogen ionRXN0-22013-Hydroxyisobutyric acid + NAD <> 2-Aminomalonate semialdehyde + NADH2-Aminomalonate semialdehyde + NADPH + Hydrogen ion <> NADP + L-SerinePW_R005862