Details of Metabolite

General Information of MET (ID: META00655)
Name Methotrexate
Synonyms   Click to Show/Hide Synonyms of This Metabolite
4-Amino-10-methylfolate; 4-Amino-10-methylfolic acid; 4-Amino-N(10)-methylpteroylglutamate; 4-Amino-N(10)-methylpteroylglutamic acid; Amethopterin; Amethopterine; Dicesium salt methotrexate; Emtexate; Emtexic acid; HDMTX; Hydrate, methotrexate; L-Amethopterin; Ledertrexate; Ledertrexic acid; MTX; Methopterin; Methotextrate; Methotrexat; Methotrexate hydrate; Methotrexate sodium; Methotrexate, (D)-isomer; Methotrexate, (DL)-isomer; Methotrexate, dicesium salt; Methotrexate, disodium salt; Methotrexate, sodium salt; Methotrexatum; Methotrexic acid; Methylaminopterin; Methylaminopterinum; Metotrexato; Mexate; N-Bismethylpteroylglutamic acid; N-[4-[[(2,4-Diamino-6-pteridinyl)methyl]methylamino]benzoyl]-L-glutamate; N-[4-[[(2,4-Diamino-6-pteridinyl)methyl]methylamino]benzoyl]-L-glutamic acid; Otrexup; Rheumatrex; Sodium, methotrexate; Trexall; Xatmep
Source Aromatic heteropolycyclic compounds
Structure Type   Amino acids, peptides, and analogues  (Click to Show/Hide the Complete Structure Type Hierarchy)
Organic acids and derivatives
Carboxylic acids and derivatives
Amino acids, peptides, and analogues
PubChem CID
126941
HMDB ID
HMDB0014703
Formula
C20H22N8O5
Structure
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3D MOL 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
KEGG ID
C01937
DrugBank ID
DB00563
ChEBI ID
44185
ChemSpider ID
112728
Physicochemical Properties Molecular Weight 454.4 Topological Polar Surface Area 211
XlogP -1.8 Complexity 704
Heavy Atom Count 33 Rotatable Bond Count 9
Hydrogen Bond Donor Count 5 Hydrogen Bond Acceptor Count 12
Function
Methotrexate is only found in individuals that have used or taken this drug. It is an antineoplastic antimetabolite with immunosuppressant properties. It is an inhibitor of tetrahydrofolate dehydrogenase and prevents the formation of tetrahydrofolate, necessary for synthesis of thymidylate, an essential component of DNA. Methotrexate anti-tumor activity is a result of the inhibition of folic acid reductase, leading to inhibition of DNA synthesis and inhibition of cellular replication. The mechanism involved in its activity against rheumatoid arthritis is not known.
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      Organic ion transporter (OIT)
            Solute carrier family 22 member 7 (SLC22A7) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [1]
                      Introduced Variation Overexpression of SLC22A7
                      Induced Change Methotrexate concentration: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that overexpression of SLC22A7 leads to the increase of methotrexate levels compared with control group.
References
1 Interaction of human organic anion transporters 2 and 4 with organic anion transport inhibitors. J Pharmacol Exp Ther. 2002 Jun;301(3):797-802.

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