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CHEBI:44185 - methotrexate
| Formula | C20H22N8O5 |
| Net Charge | 0 |
| Average Mass | 454.447 |
| Monoisotopic Mass | 454.17132 |
| SMILES | CN(Cc1cnc2nc(N)nc(N)c2n1)c1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1 |
| InChI | InChI=1S/C20H22N8O5/c1-28(9-11-8-23-17-15(24-11)16(21)26-20(22)27-17)12-4-2-10(3-5-12)18(31)25-13(19(32)33)6-7-14(29)30/h2-5,8,13H,6-7,9H2,1H3,(H,25,31)(H,29,30)(H,32,33)(H4,21,22,23,26,27)/t13-/m0/s1 |
| InChIKey | FBOZXECLQNJBKD-ZDUSSCGKSA-N |
| Wikipedia |
|---|
| Roles Classification |
|---|
| Chemical Role: | Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Brønsted base). |
| Biological Roles: | DNA synthesis inhibitor Any substance that inhibits the synthesis of DNA. immunosuppressive agent An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response. antimetabolite A substance which is structurally similar to a metabolite but which competes with it or replaces it, and so prevents or reduces its normal utilization. EC 1.5.1.3 (dihydrofolate reductase) inhibitor An EC 1.5.1.* (oxidoreductase acting on donor CH-NH group, NAD+ or NADP+ as acceptor) inhibitor that interferes with the action of dihydrofolate reductase (EC 1.5.1.3). |
| Applications: | dermatologic drug A drug used to treat or prevent skin disorders or for the routine care of skin. antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms. immunosuppressive agent An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response. abortifacient A chemical substance that interrupts pregnancy after implantation. antirheumatic drug A drug used to treat rheumatoid arthritis. |
| ChEBI Ontology |
|---|
| Outgoing Relation(s) |
| methotrexate (CHEBI:44185) has functional parent L-glutamic acid (CHEBI:16015) |
| methotrexate (CHEBI:44185) has role abortifacient (CHEBI:50691) |
| methotrexate (CHEBI:44185) has role antimetabolite (CHEBI:35221) |
| methotrexate (CHEBI:44185) has role antineoplastic agent (CHEBI:35610) |
| methotrexate (CHEBI:44185) has role antirheumatic drug (CHEBI:35842) |
| methotrexate (CHEBI:44185) has role dermatologic drug (CHEBI:50177) |
| methotrexate (CHEBI:44185) has role DNA synthesis inhibitor (CHEBI:59517) |
| methotrexate (CHEBI:44185) has role EC 1.5.1.3 (dihydrofolate reductase) inhibitor (CHEBI:50683) |
| methotrexate (CHEBI:44185) has role immunosuppressive agent (CHEBI:35705) |
| methotrexate (CHEBI:44185) is a dicarboxylic acid (CHEBI:35692) |
| methotrexate (CHEBI:44185) is a monocarboxylic acid amide (CHEBI:29347) |
| methotrexate (CHEBI:44185) is a pteridines (CHEBI:26373) |
| methotrexate (CHEBI:44185) is conjugate acid of methotrexate(1−) (CHEBI:50680) |
| Incoming Relation(s) |
| methotrexate(1−) (CHEBI:50680) is conjugate base of methotrexate (CHEBI:44185) |
| IUPAC Name |
|---|
| N-(4-{[(2,4-diaminopteridin-6-yl)methyl](methyl)amino}benzoyl)-L-glutamic acid |
| INNs | Source |
|---|---|
| methotrexate | KEGG DRUG |
| methotrexatum | ChemIDplus |
| metotrexato | ChemIDplus |
| Synonyms | Source |
|---|---|
| Methotrexate | KEGG COMPOUND |
| N-[4-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]benzoyl]-L-glutamic acid | NIST Chemistry WebBook |
| 4-amino-N10-methylpteroylglutamic acid | NIST Chemistry WebBook |
| METHOTREXATE | PDBeChem |
| MTX | ChemIDplus |
| 4-amino-10-methylfolic acid | ChemIDplus |
| Brand Names | Source |
|---|---|
| Emtexate | DrugBank |
| Ledertrexate | DrugBank |
| Rheumatrex | DrugBank |
| Trexall | DrugBank |