Methotrexate
C20H22N8O5, 454.447 g/mol. Its structure, the values that were measured, the values that were calculated, and where each one came from.
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
- CN(Cc1cnc2nc(N)nc(N)c2n1)c1ccc(C(=O)NC(CCC(=O)O)C(=O)O)cc1
- CN(Cc1cnc2nc(N)nc(N)c2n1)c1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1
- 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
- FBOZXECLQNJBKD-ZDUSSCGKSA-N
Measured properties
Values somebody obtained from a sample and published. Where two sources report the same property they are both shown, in the units each used — a disagreement between them is information, and averaging it away would be inventing a number neither one gave.
- Melting Point
- 365 to 399 °F (decomposes) (NTP, 1992)
- 195 °C
- Solubility
- less than 1 mg/mL at 66 °F (NTP, 1992)
- Insoluble in water , alcohol, chloroform, ether; slightly soluble in dilute hydrochloric acid; soluble in dil solns of alkali hydroxides and carbonates.
- Vapor Pressure
- 2.1X10-19 mm Hg at 25 °C /Estimated/
- LogP
- -1.85
- log Kow = -1.85
Calculated properties
Derived from the structure rather than from a sample. These are reproducible and they are not measurements: a calculated partition coefficient and a measured one can differ by a long way, and where both exist they are listed apart on purpose.
- Molecular weight
- 454.4 g/mol
- Exact mass
- 454.17131583 Da
- XLogP3
- -1.8
- Polar surface area
- 211 Ų
- Complexity
- 704
- H-bond donors
- 5
- H-bond acceptors
- 12
- logP
- 0.2684
- Topological polar surface area
- 210.54 Ų
- H-bond donors
- 5
- H-bond acceptors
- 10
- Rotatable bonds
- 9
- Molar refractivity
- 118.2616 cm³/mol
- Fraction sp³ carbons
- 0.25
- QED drug-likeness
- 0.2947
What it is made of
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
Amide
Primary aromatic amine
Tertiary aromatic amine
Aromatic ring
The molecule in three dimensions
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
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
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.
Where these values came from
chemistry engine
What this page does not claim
The identifiers are what the source record holds, copied rather than recomputed. Measured values are reported as their source gave them, units and all; calculated values are marked as calculated and are not measurements. Where a field is absent the page says so, because a blank cell reads as a zero and a guessed value reads as a fact.
Nothing here is a hazard assessment, a purity statement or advice about handling a sample. A flash point quoted from a safety database is a number somebody published, not a judgement by us about whether this molecule is safe for what you intend.