Raltitrexed (CED0006246)

Record Information

Version

1.0

Creation Date

2016-05-22 05:45:56 UTC

Update Date

2026-08-21 18:49:06 UTC

Accession Number

CHEM019027

Identification

Common Name

Raltitrexed

Class

Small Molecule

Description

Raltitrexed is an organic compound with the formula C21H22N4O6S and an average molecular weight of 458.49 g/mol. Raltitrexed belongs to the amino acids, peptides, and analogues, a subclass of carboxylic acids and derivatives within the organic compounds. This compound acts as an antagonist or inhibitor of thymidylate synthase (TYMS) and targets both thymidylate synthase (TMP1) and mitochondrial folylpolyglutamate synthase (FPGS). The substance is found in or released from two recorded sources: electrical and electronic equipment (line transmission systems) and healthcare, pharmaceuticals & veterinary products (antineoplastic agents). The recorded route of exposure for this compound is intravenous.

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
ZD1694	Kegg
Tomudex	Kegg
ZD-1694	HMDB
ICI-D1694	HMDB
N-(5-(N-(3,4-Dihydro-2-methyl-4-oxoquinazolin-6-ylmethyl)-N-methylamino)-2-thenoyl)-L-glutamic acid	HMDB
Arkomédika brand OF raltitrexed	HMDB
AstraZeneca brand OF raltitrexed	HMDB
ICI D1694	HMDB
Zeneca brand OF raltitrexed	HMDB
Raltitrexed	KEGG

Chemical Formula

C₂₁H₂₂N₄O₆S

Average Molecular Mass

458.488 g/mol

Monoisotopic Mass

458.126 g/mol

CAS Registry Number

112887-68-0

IUPAC Name

(2S)-2-[(5-{methyl[(2-methyl-4-oxo-1,4-dihydroquinazolin-6-yl)methyl]amino}thiophen-2-yl)formamido]pentanedioic acid

Traditional Name

raltitrexed

SMILES

CN(CC1=CC2=C(NC(C)=NC2=O)C=C1)C1=CC=C(S1)C(=O)N[C@@H](CCC(O)=O)C(O)=O

InChI Identifier

InChI=1S/C21H22N4O6S/c1-11-22-14-4-3-12(9-13(14)19(28)23-11)10-25(2)17-7-6-16(32-17)20(29)24-15(21(30)31)5-8-18(26)27/h3-4,6-7,9,15H,5,8,10H2,1-2H3,(H,24,29)(H,26,27)(H,30,31)(H,22,23,28)/t15-/m0/s1

InChI Key

IVTVGDXNLFLDRM-HNNXBMFYSA-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
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Diazanaphthalene
Quinazoline
2-heteroaryl carboxamide
Thiophene carboxamide
Thiophene carboxylic acid or derivatives
Dialkylarylamine
Hydroxypyrimidine
2,5-disubstituted thiophene
Pyrimidine
Dicarboxylic acid or derivatives
2-aminothiophene
Benzenoid
Heteroaromatic compound
Thiophene
Carboxamide group
Secondary carboxylic acid amide
Azacycle
Carboxylic acid
Organoheterocyclic compound
Carbonyl group
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

N-acyl-amino acid (CHEBI:5847 )

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	0.018 g/L	ALOGPS
logP	1.65	ALOGPS
logP	1.97	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	3.72	ChemAxon
pKa (Strongest Basic)	-0.46	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	148.4 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	117.39 m³·mol⁻¹	ChemAxon
Polarizability	45.55 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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	splash10-03dl-2443900000-4123f916ebf757efa490	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-00dr-7321290000-bce279f690f228594cb4	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-03k9-0709000000-b0a922c0009fee349863	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0229-0905000000-8495738b2ade19f86c55	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-0141900000-ff3efc6165c65f4a9024	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-074l-0512900000-f514d4a6b300e1598c10	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0h90-0932200000-df9ed4d0d58576d2bb3f	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-0910000000-639daf8403905e6f1108	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-0290000000-b82035dbae7250dd815a	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0bvj-0695700000-22b802197672293574e8	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0r09-6940000000-c21b12820e7259aeaa79	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-0002900000-ab80ccf8854a5fa05e39	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03di-0309000000-662b7467b152c14db878	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03nc-0964000000-03c9a6de56b48b2a5430	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0671-0294800000-11e71794a8ea12903210	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004j-2839600000-da164ebd563c294893c2	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-066r-1893200000-ac9baba8ea2c00c97300	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
8558.0	Log mg/kg	[4800:15000]	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
525	Line Transmission Systems	Electrical & Electronic Equipment	Not Available

Pathways

2 pathways

Raltitrexed Action Pathway

Raltitrexed Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Thymidylate synthase	P45352	Rattus norvegicus	Predicted (SEA)	0.0778492
Click to view 3D structure	Thymidylate synthase	P07607	Mus musculus	Predicted (SEA)	1.24559
Click to view 3D structure	Thymidylate synthase	P04818	Humans	Predicted (SEA)	1.08989
Click to view 3D structure	Dihydrofolate reductase	P00374	Humans	Predicted (SEA)	5.2159
Click to view 3D structure	Thymidylate synthase	P00469	Lactobacillus casei	Predicted (SEA)	1.16774
Click to view 3D structure	Thymidylate synthase	C3SWJ7	Escherichia coli	Predicted (SEA)	0.389246
Click to view 3D structure	Proton-coupled folate transporter	Q96NT5	Humans	Predicted (SEA)	0.467095
Click to view 3D structure	Bifunctional dihydrofolate reductase-thymidylate synthase	Q07422	Toxoplasma gondii	Predicted (SEA)	3.58106
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)	0.622794
Click to view 3D structure	Dihydrofolate reductase	Q920D2	Rattus norvegicus	Predicted (SEA)	9.03051
Click to view 3D structure	Trifunctional purine biosynthetic protein adenosine-3	Q64737	Mus musculus	Predicted (SEA)	2.88042
Click to view 3D structure	Dihydrofolate reductase	P00375	Mus musculus	Predicted (SEA)	4.43741
Click to view 3D structure	Trifunctional purine biosynthetic protein adenosine-3	P22102	Humans	Predicted (SEA)	3.81461
Click to view 3D structure	Dihydrofolate reductase	P00381	Lactobacillus casei	Predicted (SEA)	11.366
Click to view 3D structure	Thymidylate synthase (EC 2.1.1.45) (TS) (TSase)	E2QDN0	Escherichia coli	Predicted (SEA)	1.32344
Click to view 3D structure	Dihydrofolate reductase	P00380	Enterococcus faecium	Predicted (SEA)	4.35956
Click to view 3D structure	Bifunctional purine biosynthesis protein ATIC	P31939	Humans	Predicted (SEA)	3.89246
Click to view 3D structure	Thymidylate synthase	P0A884	Escherichia coli (strain K12)	Predicted (SEA)	0.311397
Click to view 3D structure	Dihydrofolate reductase	P16184	Pneumocystis carinii	Predicted (SEA)	15.1806
Click to view 3D structure	Dihydrofolate reductase	P0ABQ4	Escherichia coli (strain K12)	Predicted (SEA)	16.2705
Click to view 3D structure	Dihydrofolate synthase/folylpolyglutamate synthase	P08192	Escherichia coli (strain K12)	Predicted (SEA)	3.42537
Click to view 3D structure	Solute carrier organic anion transporter family member 1A3	P70502	Rattus norvegicus	Predicted (SEA)	4.28171
Click to view 3D structure	Histone-lysine N-methyltransferase EHMT2	Q96KQ7	Humans	Predicted (SEA)	35.5771