ChemFOnt: Showing chemical card for Methotrexate (CFc000009055)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:56:04 UTC

Chemfont ID

CFc000009055

Molecule Identification

Common Name

Methotrexate

Definition

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. [PubChem]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.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
4-Amino-10-methylfolic acid	ChEBI
4-Amino-N(10)-methylpteroylglutamic acid	ChEBI
Emtexate	ChEBI
Ledertrexate	ChEBI
Methotrexatum	ChEBI
Metotrexato	ChEBI
MTX	ChEBI
N-[4-[[(2,4-Diamino-6-pteridinyl)methyl]methylamino]benzoyl]-L-glutamic acid	ChEBI
Rheumatrex	ChEBI
Trexall	ChEBI
Otrexup	Kegg
Xatmep	Kegg
4-Amino-10-methylfolate	Generator
4-Amino-N(10)-methylpteroylglutamate	Generator
Emtexic acid	Generator
Ledertrexic acid	Generator
N-[4-[[(2,4-Diamino-6-pteridinyl)methyl]methylamino]benzoyl]-L-glutamate	Generator
Methotrexic acid	Generator
Amethopterin	HMDB
Amethopterine	HMDB
HDMTX	HMDB
L-Amethopterin	HMDB
Methopterin	HMDB
Methotextrate	HMDB
Methotrexat	HMDB
Methylaminopterin	HMDB
Methylaminopterinum	HMDB
N-Bismethylpteroylglutamic acid	HMDB
Hydrate, methotrexate	HMDB
Methotrexate, disodium salt	HMDB
Methotrexate, sodium salt	HMDB
Methotrexate, (DL)-isomer	HMDB
Sodium, methotrexate	HMDB
Dicesium salt methotrexate	HMDB
Methotrexate hydrate	HMDB
Methotrexate, dicesium salt	HMDB
Mexate	HMDB
Methotrexate sodium	HMDB
Methotrexate, (D)-isomer	HMDB

Chemical Formula

C₂₀H₂₂N₈O₅

Average Molecular Weight

454.4393

Monoisotopic Molecular Weight

454.171315854

IUPAC Name

(2S)-2-[(4-{[(2,4-diaminopteridin-6-yl)methyl](methyl)amino}phenyl)formamido]pentanedioic acid

Traditional Name

methotrexate

CAS Registry Number

59-05-2

SMILES

CN(CC1=CN=C2N=C(N)N=C(N)C2=N1)C1=CC=C(C=C1)C(=O)N[C@@H](CCC(O)=O)C(O)=O

InChI Identifier

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

InChI Key

FBOZXECLQNJBKD-ZDUSSCGKSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Glutamic acid and derivatives

Alternative Parents

Substituents

Glutamic acid or derivatives
Hippuric acid or derivatives
Hippuric acid
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Aminobenzamide
Aminobenzoic acid or derivatives
Pteridine
Benzamide
Benzoic acid or derivatives
Benzoyl
Aniline or substituted anilines
Tertiary aliphatic/aromatic amine
Dialkylarylamine
Aminopyrimidine
Aralkylamine
Benzenoid
Pyrimidine
Pyrazine
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Heteroaromatic compound
Tertiary amine
Secondary carboxylic acid amide
Carboxamide group
Amino acid
Carboxylic acid
Organoheterocyclic compound
Azacycle
Organic oxygen compound
Primary amine
Carbonyl group
Amine
Organic oxide
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

monocarboxylic acid amide (CHEBI:44185 )
dicarboxylic acid (CHEBI:44185 )
pteridines (CHEBI:44185 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0014703)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Methotrexate Action Pathway (PathBank: SMP0000432)

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.17 g/L	ALOGPS
logP	-0.91	ALOGPS
logP	-0.24	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	3.26	ChemAxon
pKa (Strongest Basic)	1.8	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	210.54 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	119.21 m³·mol⁻¹	ChemAxon
Polarizability	44.54 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon