Methotrexate

An aromatic carboxylic acid, C20H22N8O5, 454.447 g/mol. Melting point 195 °C, as published.

verified recordOrganic — aromatic carboxylic acid4 measured properties

Identifiers

Molecular formula: C₂₀H₂₂N₈O₅
Molecular weight: 454.447 g/mol
Exact mass: 454.171316 g/mol
IUPAC name: (2S)-2-[[4-[(2,4-diaminopteridin-6-yl)methyl-methylamino]benzoyl]amino]pentanedioic acid
SMILES: CN(Cc1cnc2nc(N)nc(N)c2n1)c1ccc(C(=O)NC(CCC(=O)O)C(=O)O)cc1
Isomeric 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

Open in ReactionLens Use in reaction prediction

Measured properties

Published measurements, each with its source. Two readings of one property are both shown, in the units each used.

Melting Point: 365 to 399 °F (decomposes) (NTP, 1992)measured · CAMEO Chemicals; 195 °Cmeasured · DrugBank
Solubility: less than 1 mg/mL at 66 °F (NTP, 1992)measured · CAMEO Chemicals; Insoluble in water , alcohol, chloroform, ether; slightly soluble in dilute hydrochloric acid; soluble in dil solns of alkali hydroxides and carbonates.measured · Hazardous Substances Data Bank (HSDB)
Vapor Pressure: 2.1X10-19 mm Hg at 25 °C /Estimated/measured · Hazardous Substances Data Bank (HSDB)
LogP: -1.85measured · DrugBank; log Kow = -1.85measured · Hazardous Substances Data Bank (HSDB)

Calculated properties

Derived from the structure, not from a sample; kept apart from the measurements above.

Molecular weight: 454.4 g/molcalculated · reference compound database; Average mass of one molecule, from reference compound database.
Exact mass: 454.17131583 Dacalculated · reference compound database; Mass of the most common isotopic form.
XLogP3: -1.8calculated · reference compound database; Estimated oil/water partition, computed by reference compound database.
Polar surface area: 211 Å²calculated · reference compound database; Polar surface area as computed by reference compound database.
Complexity: 704calculated · reference compound database; A rough measure of how intricate the structure is.
H-bond donors: 5calculated · reference compound database
H-bond acceptors: 12calculated · reference compound database
logP: 0.2684calculated · chemistry engine; Estimated preference for oil over water. Higher means more oil-like.
Topological polar surface area: 210.54 Å²calculated · chemistry engine; Surface area from polar atoms; relates to how easily a molecule crosses membranes.
H-bond donors: 5calculated · chemistry engine; Atoms that can donate a hydrogen bond.
H-bond acceptors: 10calculated · chemistry engine; Atoms that can accept a hydrogen bond.
Rotatable bonds: 9calculated · chemistry engine; Single bonds the molecule can freely twist around.
Molar refractivity: 118.2616 cm³/molcalculated · chemistry engine; Relates to the molecule's polarisability.
Fraction sp³ carbons: 0.25calculated · chemistry engine; Share of carbon atoms with tetrahedral bonding.
QED drug-likeness: 0.2947calculated · chemistry engine; Quantitative estimate of drug-likeness (0–1).

What it is made of

Elements

C Carbon20 atoms · 52.9% by mass
N Nitrogen8 atoms · 24.7% by mass
O Oxygen5 atoms · 17.6% by mass
H Hydrogen22 atoms · 4.9% by mass

Percentages are of the molecular weight above, worked out the same way the molar mass calculator does it.

Structure

Heavy atoms, hydrogen excluded: 33
Total atoms, hydrogen included: 55
Rings: 3
Aromatic rings: 3
Stereocentres: 1
Formal charge: 0

Functional groups

Carboxylic acid
A carbon double-bonded to oxygen and bonded to an –OH group; acidic.
Amide
A carbonyl bonded directly to nitrogen.
Primary aromatic amine
An –NH2 group attached directly to an aromatic ring, as in aniline. Much less basic than an alkyl amine, because the lone pair is delocalised into the ring.
Tertiary aromatic amine
A nitrogen bonded to an aromatic ring and two other carbons.
Aromatic ring
A flat six-membered ring with delocalised electrons.

Matched by structural pattern, not by a measurement.

The molecule in three dimensions

Rotate and inspect the atoms. Loaded only when you ask, so the page stays light.

The drawing above is a diagram of what is bonded to what. A molecule is not flat, and the model here is one low-energy shape generated from the connectivity — useful for seeing which groups can reach each other, and not a measured structure. A real sample is a population of conformations, interconverting.

Reactions it appears in

No documented reaction with a written procedure and a source involves Methotrexate yet.

Other names for it

The systematic name on this record is (2S)-2-[[4-[(2,4-diaminopteridin-6-yl)methyl-methylamino]benzoyl]amino]pentanedioic acid.

The sources also call it Rheumatrex, Amethopterin, Metatrexan, Hdmtx, Ledertrexate, Methylaminopterinum, Methotrexatum, Metotrexato, Antifolan, Rasuvo, Emtexate.

Structurally related

Nothing structurally close to Methotrexate has a page here yet.

Seen alongside it in reaction records

Molecules that appear in the same recorded reactions as Methotrexate. This says nothing about structure: most of them are the bases, solvents, ligands and catalysts the chemistry needed, and they are here because somebody put them in the same flask.

(2S)-2-[[4-[(2,4-diaminopteridin-6-yl)methyl-methylamino]phenyl]methylamino]pentanedioic acid

formed as a product

C₂₀H₂₄N₈O₄, 440.464 g/mol.

Where these values came from

reference compound database126941
compound record
chemistry engine
structure perception

compound record.

What this page does not claim

Identifiers are copied from the source record, measured values are reported as published, and calculated values are marked as calculated. Nothing here is a hazard, purity or handling assessment — how the library is checked.