1.02011-09-21 00:18:11 UTC2015-10-09 22:30:45 UTCFDB022702AminopterinAminopterin 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-deoxypteroylglutamate4-Amino-PGA4-Aminofolate4-Aminofolic acid4-Aminopteroylglutamate4-Aminopteroylglutamic acidAminopterinAminopterineAPGAL-N-[p-[[(2,4-diamino-6-pteridinyl)methyl]amino]benzoyl]-Glutamic acidPteraminaC19H20N8O5440.4127440.155665792-[(4-{[(2,4-diaminopteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acidaminopterin54-62-6NC1=NC2=C(N=C(CNC3=CC=C(C=C3)C(=O)NC(CCC(O)=O)C(O)=O)C=N2)C(N)=N1InChI=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 acidsOrganic compoundsOrganoheterocyclic compoundsPteridines and derivativesPterins and derivativesAromatic heteropolycyclic compoundsAmino acidsAminobenzamidesAminopyrimidines and derivativesAniline and substituted anilinesAzacyclic compoundsBenzoyl derivativesCarbonyl compoundsCarboxylic acidsDicarboxylic acids and derivativesGlutamic acid and derivativesHeteroaromatic compoundsHippuric acidsHydrocarbon derivativesImidolactamsN-acyl-alpha amino acidsOrganic oxidesOrganopnictogen compoundsPhenylalkylaminesPrimary aminesPyrazinesSecondary alkylarylaminesSecondary carboxylic acid amidesAlpha-amino acid or derivativesAmineAmino acidAmino acid or derivativesAminobenzamideAminobenzoic acid or derivativesAminopyrimidineAniline or substituted anilinesAralkylamineAromatic heteropolycyclic compoundAzacycleBenzamideBenzenoidBenzoic acid or derivativesBenzoylCarbonyl groupCarboxamide groupCarboxylic acidCarboxylic acid derivativeDicarboxylic acid or derivativesFolic acidGlutamic acid or derivativesHeteroaromatic compoundHippuric acidHippuric acid or derivativesHydrocarbon derivativeImidolactamMonocyclic benzene moietyN-acyl-alpha amino acid or derivativesN-acyl-alpha-amino acidOrganic nitrogen compoundOrganic oxideOrganic oxygen compoundOrganonitrogen compoundOrganooxygen compoundOrganopnictogen compoundPhenylalkylaminePrimary aminePyrazinePyrimidineSecondary aliphatic/aromatic amineSecondary amineSecondary carboxylic acid amideSolidlogp-0.25logs-3.62solubility1.06e-01 g/llogp-0.95pka_strongest_acidic3.38pka_strongest_basic2.25iupac2-[(4-{[(2,4-diaminopteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acidaverage_mass440.4127mono_mass440.15566579smilesNC1=NC2=C(N=C(CNC3=CC=C(C=C3)C(=O)NC(CCC(O)=O)C(O)=O)C=N2)C(N)=N1formulaC19H20N8O5inchiInChI=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)inchikeyTVZGACDUOSZQKY-UHFFFAOYSA-Npolar_surface_area219.33refractivity114.98polarizability44.13rotatable_bond_count9acceptor_count12donor_count6physiological_charge-2formal_charge0Specdb::CMs9873Specdb::CMs38140Specdb::CMs131109Specdb::CMs138843Specdb::NmrTwoD1687Specdb::NmrOneD1747Specdb::NmrOneD148320Specdb::NmrOneD148321Specdb::NmrOneD148322Specdb::NmrOneD148323Specdb::NmrOneD148324Specdb::NmrOneD148325Specdb::NmrOneD148326Specdb::NmrOneD148327Specdb::NmrOneD148328Specdb::NmrOneD148329Specdb::NmrOneD148330Specdb::NmrOneD148331Specdb::NmrOneD148332Specdb::NmrOneD148333Specdb::NmrOneD148334Specdb::NmrOneD148335Specdb::NmrOneD148336Specdb::NmrOneD148337Specdb::NmrOneD148338Specdb::NmrOneD148339Specdb::MsMs1687Specdb::MsMs1688Specdb::MsMs1689Specdb::MsMs287821Specdb::MsMs287822Specdb::MsMs287823Specdb::MsMs326758Specdb::MsMs326759Specdb::MsMs326760Specdb::MsMs2387831Specdb::MsMs2387832Specdb::MsMs2387833Specdb::MsMs2578521Specdb::MsMs2578522Specdb::MsMs2578523HMDB01833#<Reference:0x00005556759c3288>#<Reference:0x00005556759c30a8>#<Reference:0x00005556759c2ea0>#<Reference:0x00005556759c2cc0>