(2S)-2-[(5-{methyl[(2-methyl-4-oxo-3,4-dihydroquinazolin-6-yl)methyl]amino}thiophen-2-yl)formamido]pentanedioic acid hydrate

• ChemBase ID: 154385
• Molecular Formular: C21H24N4O7S
• Molecular Mass: 476.50286
• Monoisotopic Mass: 476.13657013
• SMILES: Cc1[nH]c(=O)c2cc(ccc2n1)CN(C)c1ccc(s1)C(=O)N[C@@H](CCC(=O)O)C(=O)O.O
• Canonical SMILES: OC(=O)CC[C@@H](C(=O)O)NC(=O)c1ccc(s1)N(Cc1ccc2c(c1)c(=O)[nH]c(n2)C)C.O
• InChI: InChI=1S/C21H22N4O6S.H2O/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);1H2/t15-;/m0./s1
• InChIKey: VADKIFZZQGWGDT-RSAXXLAASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(5-{methyl[(2-methyl-4-oxo-3,4-dihydroquinazolin-6-yl)methyl]amino}thiophen-2-yl)formamido]pentanedioic acid hydrate
• IUPAC Traditional name: (2S)-2-[(5-{methyl[(2-methyl-4-oxo-3H-quinazolin-6-yl)methyl]amino}thiophen-2-yl)formamido]pentanedioic acid hydrate
• Synonyms: L-Glutamic acid, N-((5-(((1,4-dihydro-2-methyl-4-oxo-6-quinazolinyl)methyl)methylamino)-2-thienyl)carbonyl)- monohydrate; ICI-D-1694; ZD-1694; Raltitrexed monohydrate

Database IDs

• MDL Number: MFCD12828867
• PubChem SID: 162248524
• PubChem CID: 14256589

CALCULATED PROPERTIES

• Acid pKa: 3.9605484
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -1.3607305
• LogD (pH = 7.4): -4.7035975
• Log P: 0.7630046
• Molar Refractivity: 117.8249 cm^3
• Polarizability: 43.176983 Å^3
• Polar Surface Area: 148.4 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥40 mg/mL; H2O: ≥10 mg/mL
• Apperance: off-white to light yellow solid

Safety Information

• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 2
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 61-25
• Safety Statements: 53-45
• GHS Pictograms: GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H300-H360
• GHS Precautionary statements: P201-P264-P301 + P310-P308 + P313
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C21H22N4O6S · H2O

DETAILS

Sigma Aldrich - R9156

Biochem/physiol Actions
Raltitrexed is a folate-based inhibitor of thymidylate synthase (TS) that is rapidly and extensively metabolized to its more potent polyglutamate derivatives. By inhibiting the formation of precursor pyrimidine nucleotides, raltitrexed prevents the formation of DNA and RNA, which are required for the growth and survival of both normal cells and cancer cells.