pemetrexed (CED0001892)

Record Information

Version

1.0

Creation Date

2016-06-03 11:54:45 UTC

Update Date

2026-05-14 16:44:53 UTC

Accession Number

CHEM044243

Identification

Common Name

pemetrexed

Class

Small Molecule

Description

Pemetrexed is an organic compound with the chemical formula C20H21N5O6 and an average molecular weight of 427.41 g/mol. Pemetrexed belongs to the amino acids, peptides, and analogues, a subclass of carboxylic acids and derivatives within the organic compounds. This compound is found in or released from two recorded sources: antennas within electrical and electronic equipment, and antineoplastic agents within healthcare, pharmaceuticals, and veterinary products. Recorded routes of exposure include intraventricular and intravenous administration. Pemetrexed acts on five recorded protein targets. It functions as an inhibitor of thymidylate synthase (TYMS), dihydrofolate reductase (DHFR), the bifunctional purine biosynthesis protein ATIC, and the trifunctional purine biosynthetic protein adenosine-3 (GART), as well as one other protein.

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
LY231514	HMDB
Pemetrexed disodium	HMDB
MTA	HMDB
N-(4-(2-(2-Amino-3,4-dihydro-4-oxo-7H-pyrrolo(2,3-D)pyrimdin-5-yl)ethyl)benzoyl)glutamic acid	HMDB
Disodium, pemetrexed	HMDB
ALIMTA	HMDB
(2R)-2-{[4-(2-{4-hydroxy-2-imino-1H,2H,7H-pyrrolo[2,3-D]pyrimidin-5-yl}ethyl)phenyl]formamido}pentanedioate	Generator
Pemetrexed	MeSH

Chemical Formula

C₂₀H₂₁N₅O₆

Average Molecular Mass

427.411 g/mol

Monoisotopic Mass

427.149 g/mol

CAS Registry Number

137281-23-3

IUPAC Name

(2R)-2-{[4-(2-{2-amino-4-oxo-1H,4H,7H-pyrrolo[2,3-d]pyrimidin-5-yl}ethyl)phenyl]formamido}pentanedioic acid

Traditional Name

pemetrexed

SMILES

NC1=NC(=O)C2=C(NC=C2CCC2=CC=C(C=C2)C(=O)N[C@H](CCC(O)=O)C(O)=O)N1

InChI Identifier

InChI=1S/C20H21N5O6/c21-20-24-16-15(18(29)25-20)12(9-22-16)6-3-10-1-4-11(5-2-10)17(28)23-13(19(30)31)7-8-14(26)27/h1-2,4-5,9,13H,3,6-8H2,(H,23,28)(H,26,27)(H,30,31)(H4,21,22,24,25,29)/t13-/m1/s1

InChI Key

WBXPDJSOTKVWSJ-CYBMUJFWSA-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
Benzamide
Benzoic acid or derivatives
Pyrrolo[2,3-d]pyrimidine
Pyrrolopyrimidine
Benzoyl
Hydroxypyrimidine
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Benzenoid
Substituted pyrrole
Pyrimidine
Heteroaromatic compound
Pyrrole
Secondary carboxylic acid amide
Carboxamide group
Organoheterocyclic compound
Azacycle
Carboxylic acid
Organonitrogen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.046 g/L	ALOGPS
logP	0.11	ALOGPS
logP	0.73	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	3.34	ChemAxon
pKa (Strongest Basic)	0.96	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	186.97 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	109.45 m³·mol⁻¹	ChemAxon
Polarizability	43.04 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-001l-4296100000-61f13aa328f04f219346	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-056r-1222390000-1922107d9a1510f7ea85	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-0009300000-2b11923a816fae5694ac	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03di-0124900000-823efc7fe28d46d36b1e	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-01q9-0595200000-40f20d687bf52bf25850	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0j59-2950000000-02b1adc8f50941ec6651	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-0003900000-05ee3dff6a5cb9c0f008	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-055f-7449700000-e8461ae1b25e058467dc	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0f6y-9581000000-1d564e2a04015586902a	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0059-0060900000-c08073e1cb9d840b7ae9	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-1980000000-905a773cb8f67a9df28e	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03e9-1940000000-d4ae1b2367ede6e4bc56	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0bvi-0004900000-cfe04a4c69804bd48ab7	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0pec-1907500000-a026b00353204e58661d	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udi-2910000000-3d0cf7fa7cfd8b10c881	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
2213.0	Log mg/kg	[1200:3900]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
358	Antineoplastic agents	Healthcare, pharmaceuticals & veterinary products	Not Available
506	Antennas	Electrical & Electronic Equipment	Not Available

Pathways

2 pathways

Pemetrexed Action Pathway

Pemetrexed Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Dihydrofolate reductase	P00374	Humans	Predicted (SEA)	3.73676
Click to view 3D structure	Thymidylate synthase	P04818	Humans	Predicted (SEA)	1.01204
Click to view 3D structure	Trifunctional purine biosynthetic protein adenosine-3	P22102	Humans	Predicted (SEA)	0.544945
Click to view 3D structure	Thymidylate synthase	P00469	Lactobacillus casei	Predicted (SEA)	1.08989
Click to view 3D structure	Dihydrofolate reductase	P00381	Lactobacillus casei	Predicted (SEA)	3.42537
Click to view 3D structure	Bifunctional dihydrofolate reductase-thymidylate synthase	Q07422	Toxoplasma gondii	Predicted (SEA)	2.41333
Click to view 3D structure	Thymidylate synthase	C3SWJ7	Escherichia coli	Predicted (SEA)	0.155698
Click to view 3D structure	Dihydrofolate reductase	P0ABQ4	Escherichia coli (strain K12)	Predicted (SEA)	3.03612
Click to view 3D structure	Proton-coupled folate transporter	Q96NT5	Humans	Predicted (SEA)	0.467095
Click to view 3D structure	Folate receptor alpha	P15328	Humans	Predicted (SEA)	0.467095
Click to view 3D structure	Reduced folate transporter	P41440	Humans	Predicted (SEA)	0.467095
Click to view 3D structure	Folate receptor beta	P14207	Humans	Predicted (SEA)	0.389246
Click to view 3D structure	Dihydrofolate reductase	P00375	Mus musculus	Predicted (SEA)	1.79053
Click to view 3D structure	Bifunctional purine biosynthesis protein ATIC	P31939	Humans	Predicted (SEA)	0.233548
Click to view 3D structure	Thymidylate synthase	P07607	Mus musculus	Predicted (SEA)	2.49118
Click to view 3D structure	Trifunctional purine biosynthetic protein adenosine-3	Q64737	Mus musculus	Predicted (SEA)	1.08989
Click to view 3D structure	Thymidylate synthase	P45352	Rattus norvegicus	Predicted (SEA)	0.389246
Click to view 3D structure	Dihydrofolate synthase/folylpolyglutamate synthase	P08192	Escherichia coli (strain K12)	Predicted (SEA)	0.233548
Click to view 3D structure	Dihydrofolate reductase	P16184	Pneumocystis carinii	Predicted (SEA)	7.16213
Click to view 3D structure	Dihydrofolate reductase	Q920D2	Rattus norvegicus	Predicted (SEA)	10.821
Click to view 3D structure	Solute carrier organic anion transporter family member 1A3	P70502	Rattus norvegicus	Predicted (SEA)	0.856341
Click to view 3D structure	Thymidylate synthase (EC 2.1.1.45) (TS) (TSase)	E2QDN0	Escherichia coli	Predicted (SEA)	0.311397
Click to view 3D structure	Bifunctional purine biosynthesis protein ATIC	Q9CWJ9	Mus musculus	Predicted (SEA)	2.02408
Click to view 3D structure	Dihydrofolate reductase	P00380	Enterococcus faecium	Predicted (SEA)	4.12601
Click to view 3D structure	Folylpolyglutamate synthase, mitochondrial	P48760	Mus musculus	Predicted (SEA)	3.58106