ChemFOnt: Showing chemical card for Raltitrexed (CFc000008823)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:55:45 UTC

Chemfont ID

CFc000008823

Molecule Identification

Common Name

Raltitrexed

Definition

Raltitrexed is only found in individuals that have used or taken this drug. It is a chemotherapy drug manufactured AstraZeneca Company, is an antimetabolite used in chemotherapy. It is an inhibitor of thymidylate synthase.Raltitrexed is an antineoplastic Agents and folic acid antagonists. Raltitrexed inhibits thymidylate synthase (TS) leading to DNA fragmentation and cell death. It is transported into cells via a reduced folate carrier. Inside the cell Raltitrexed is extensively polyglutamated, which enhances thymidylate synthase inhibitory power and duration. Inhibition of this enzyme results in decreased synthesis of thymidine triphosphate which is required for DNA synthesis.

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 Weight

458.488

Monoisotopic Molecular Weight

458.126005146

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

CAS Registry Number

112887-68-0

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 )

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

Cytoplasm (HMDB: HMDB0014438)

Source

Exogenous

Exogenous (HMDB: HMDB0014438)

Process

Not Available

Role

Not Available

Physical Properties

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