CHEBI:44185 - methotrexate

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ChEBI Name methotrexate
ChEBI ID CHEBI:44185
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:44183, CHEBI:6837
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Formula C20H22N8O5
Net Charge 0
Average Mass 454.43960
Monoisotopic Mass 454.171
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
SMILES CN(Cc1cnc2nc(N)nc(N)c2n1)c1ccc(cc1)C(=O)N[C@@H](CCC(O)=O)C(O)=O
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): 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).
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.
DNA synthesis inhibitor
Any substance that inhibits the synthesis of DNA.
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.
Application(s): 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.
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.
antirheumatic drug
A drug used to treat rheumatoid arthritis.
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ChEBI Ontology
Outgoing 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 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 Sources
methotrexate KEGG DRUG
methotrexatum ChemIDplus
metotrexato ChemIDplus
Synonyms Sources
4-amino-10-methylfolic acid ChemIDplus
4-amino-N10-methylpteroylglutamic acid NIST Chemistry WebBook
Methotrexate KEGG COMPOUND
METHOTREXATE PDBeChem
MTX ChemIDplus
N-[4-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]benzoyl]-L-glutamic acid NIST Chemistry WebBook
Brand Names Sources
Emtexate DrugBank
Ledertrexate DrugBank
Rheumatrex DrugBank
Trexall DrugBank
Database Links Databases
1751 DrugCentral
C01937 KEGG COMPOUND
D00142 KEGG DRUG
DB00563 DrugBank
LSM-5690 LINCS
Methotrexate Wikipedia
MTX PDBeChem
US2512572 Patent
View more database links
Registry Numbers Types Sources
59-05-2 CAS Registry Number NIST Chemistry WebBook
59-05-2 CAS Registry Number ChemIDplus
70669 Beilstein Registry Number Beilstein
Last Modified
22 February 2017