1.0 2011-09-21 00:18:11 UTC 2015-10-09 22:30:45 UTC FDB022702 Aminopterin Aminopterin Syndrome Sine Aminopterin (ASSA, OMIM 600325) is an embryopathy caused by maternal treatment with the olic acid antagonist aminopterin has been recognized since 1952 when aminopterin was used as an abortifacient. The characteristic phenotype of the children who survived infancy after having been exposed to aminopterin or its methyl derivative, methotrexate, in early pregnancy included a very unusual facies, skull anomalies, and skeletal defects.(OMIM); Aminopterin is an antimetabolite drug used in treatment of cancer and autoimmune diseases. It acts by inhibiting the metabolism of folic acid. - Wikipedia. The effects of the drug on intracellular metabolic processes, due to the inhibitory action on the enzyme dihydrofolate reductase, show that the result of this inhibition is more complex and is not limited to blockade of the reduction of folic acid alone. Although rescue methods are important in prevention of lethal effects of methotrexate, some metabolic pathways are insufficiently rescued, resulting in toxic reactions following methotrexate administration.(PMID 6398629) [HMDB] 4-Amino-4-deoxypteroylglutamate 4-Amino-PGA 4-Aminofolate 4-Aminofolic acid 4-Aminopteroylglutamate 4-Aminopteroylglutamic acid Aminopterin Aminopterine APGA L-N-[p-[[(2,4-diamino-6-pteridinyl)methyl]amino]benzoyl]-Glutamic acid Pteramina C19H20N8O5 440.4127 440.15566579 2-[(4-{[(2,4-diaminopteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid aminopterin 54-62-6 NC1=NC2=C(N=C(CNC3=CC=C(C=C3)C(=O)NC(CCC(O)=O)C(O)=O)C=N2)C(N)=N1 InChI=1S/C19H20N8O5/c20-15-14-16(27-19(21)26-15)23-8-11(24-14)7-22-10-3-1-9(2-4-10)17(30)25-12(18(31)32)5-6-13(28)29/h1-4,8,12,22H,5-7H2,(H,25,30)(H,28,29)(H,31,32)(H4,20,21,23,26,27) TVZGACDUOSZQKY-UHFFFAOYSA-N belongs to the class of organic compounds known as folic acids. These are heterocyclic compounds based on the 4-[(pteridin-6-ylmethyl)amino]benzoic acid skeleton conjugated with one or more L-glutamate units. Folic acids Organic compounds Organoheterocyclic compounds Pteridines and derivatives Pterins and derivatives Aromatic heteropolycyclic compounds Amino acids Aminobenzamides Aminopyrimidines and derivatives Aniline and substituted anilines Azacyclic compounds Benzoyl derivatives Carbonyl compounds Carboxylic acids Dicarboxylic acids and derivatives Glutamic acid and derivatives Heteroaromatic compounds Hippuric acids Hydrocarbon derivatives Imidolactams N-acyl-alpha amino acids Organic oxides Organopnictogen compounds Phenylalkylamines Primary amines Pyrazines Secondary alkylarylamines Secondary carboxylic acid amides Alpha-amino acid or derivatives Amine Amino acid Amino acid or derivatives Aminobenzamide Aminobenzoic acid or derivatives Aminopyrimidine Aniline or substituted anilines Aralkylamine Aromatic heteropolycyclic compound Azacycle Benzamide Benzenoid Benzoic acid or derivatives Benzoyl Carbonyl group Carboxamide group Carboxylic acid Carboxylic acid derivative Dicarboxylic acid or derivatives Folic acid Glutamic acid or derivatives Heteroaromatic compound Hippuric acid Hippuric acid or derivatives Hydrocarbon derivative Imidolactam Monocyclic benzene moiety N-acyl-alpha amino acid or derivatives N-acyl-alpha-amino acid Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Phenylalkylamine Primary amine Pyrazine Pyrimidine Secondary aliphatic/aromatic amine Secondary amine Secondary carboxylic acid amide Solid logp -0.25 ALOGPS logs -3.62 ALOGPS solubility 1.06e-01 g/l ALOGPS logp -0.95 ChemAxon pka_strongest_acidic 3.38 ChemAxon pka_strongest_basic 2.25 ChemAxon iupac 2-[(4-{[(2,4-diaminopteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid ChemAxon average_mass 440.4127 ChemAxon mono_mass 440.15566579 ChemAxon smiles NC1=NC2=C(N=C(CNC3=CC=C(C=C3)C(=O)NC(CCC(O)=O)C(O)=O)C=N2)C(N)=N1 ChemAxon formula C19H20N8O5 ChemAxon inchi InChI=1S/C19H20N8O5/c20-15-14-16(27-19(21)26-15)23-8-11(24-14)7-22-10-3-1-9(2-4-10)17(30)25-12(18(31)32)5-6-13(28)29/h1-4,8,12,22H,5-7H2,(H,25,30)(H,28,29)(H,31,32)(H4,20,21,23,26,27) ChemAxon inchikey TVZGACDUOSZQKY-UHFFFAOYSA-N ChemAxon polar_surface_area 219.33 ChemAxon refractivity 114.98 ChemAxon polarizability 44.13 ChemAxon rotatable_bond_count 9 ChemAxon acceptor_count 12 ChemAxon donor_count 6 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 9873 Specdb::CMs 38140 Specdb::CMs 131109 Specdb::CMs 138843 Specdb::NmrTwoD 1687 Specdb::NmrOneD 1747 Specdb::NmrOneD 148320 Specdb::NmrOneD 148321 Specdb::NmrOneD 148322 Specdb::NmrOneD 148323 Specdb::NmrOneD 148324 Specdb::NmrOneD 148325 Specdb::NmrOneD 148326 Specdb::NmrOneD 148327 Specdb::NmrOneD 148328 Specdb::NmrOneD 148329 Specdb::NmrOneD 148330 Specdb::NmrOneD 148331 Specdb::NmrOneD 148332 Specdb::NmrOneD 148333 Specdb::NmrOneD 148334 Specdb::NmrOneD 148335 Specdb::NmrOneD 148336 Specdb::NmrOneD 148337 Specdb::NmrOneD 148338 Specdb::NmrOneD 148339 Specdb::MsMs 1687 Specdb::MsMs 1688 Specdb::MsMs 1689 Specdb::MsMs 287821 Specdb::MsMs 287822 Specdb::MsMs 287823 Specdb::MsMs 326758 Specdb::MsMs 326759 Specdb::MsMs 326760 Specdb::MsMs 2387831 Specdb::MsMs 2387832 Specdb::MsMs 2387833 Specdb::MsMs 2578521 Specdb::MsMs 2578522 Specdb::MsMs 2578523 HMDB01833 #<Reference:0x000055ce31737828> #<Reference:0x000055ce31737558> #<Reference:0x000055ce31737238> #<Reference:0x000055ce31736fe0>