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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2022-03-07 02:51:37 UTC
HMDB IDHMDB0014438
Secondary Accession Numbers
  • HMDB14438
Metabolite Identification
Common NameRaltitrexed
DescriptionRaltitrexed, also known as tomudex or ZD1694, 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. Raltitrexed is a drug which is used for the treatment of malignant neoplasm of colon and rectum. Raltitrexed is fully active after polyglutamylation, which allows cellular retention of the drug. Raltitrexed is an extremely weak basic (essentially neutral) compound (based on its pKa). Inhibition of L1210 cell growth in culture IC50 9 nM, is one of the strongest antimetabolites in use. By inhibiting Thymidylate synthase (TS), thus 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. Raltitrexed is approved for use in Canada and some European countries, but is not approved by the US FDA.Raltitrexed is chemically similar to folic acid and is in the class of chemotherapy drugs called folate antimetabolites, which inhibit one or more of three enzymes that use folate and derivatives as substrates: DHFR, GARFT and thymidylate synthase. Structure and phase I clinical trial of the precursor drug, CB3717, was described in 1986. Used in treatment of colorectal cancer since 1998, it may also be used in the treatment of malignant mesothelioma. Raltitrexed (Tomudex, TDX, ZD 1694) is an antimetabolite drug used in cancer chemotherapy. It is an inhibitor of thymidylate synthase, and is manufactured by AstraZeneca.
Structure
Data?1582753179
Synonyms
ValueSource
ZD1694Kegg
TomudexKegg
ZD-1694HMDB
ICI-D1694HMDB
N-(5-(N-(3,4-Dihydro-2-methyl-4-oxoquinazolin-6-ylmethyl)-N-methylamino)-2-thenoyl)-L-glutamic acidHMDB
Arkomédika brand OF raltitrexedHMDB
AstraZeneca brand OF raltitrexedHMDB
ICI D1694HMDB
Zeneca brand OF raltitrexedHMDB
RaltitrexedKEGG
Chemical FormulaC21H22N4O6S
Average Molecular Weight458.488
Monoisotopic Molecular Weight458.126005146
IUPAC Name(2S)-2-[(5-{methyl[(2-methyl-4-oxo-1,4-dihydroquinazolin-6-yl)methyl]amino}thiophen-2-yl)formamido]pentanedioic acid
Traditional Nameraltitrexed
CAS Registry Number112887-68-0
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 KeyIVTVGDXNLFLDRM-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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentGlutamic 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 FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point180 - 184 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.018 g/LNot Available
LogP-1.2Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.018 g/LALOGPS
logP1.65ALOGPS
logP1.97ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)3.72ChemAxon
pKa (Strongest Basic)-0.46ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area148.4 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity117.39 m³·mol⁻¹ChemAxon
Polarizability45.55 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+202.53931661259
DarkChem[M-H]-193.88831661259
DeepCCS[M+H]+200.15730932474
DeepCCS[M-H]-197.76230932474
DeepCCS[M-2H]-230.64530932474
DeepCCS[M+Na]+206.0730932474
AllCCS[M+H]+203.232859911
AllCCS[M+H-H2O]+201.332859911
AllCCS[M+NH4]+204.932859911
AllCCS[M+Na]+205.432859911
AllCCS[M-H]-198.232859911
AllCCS[M+Na-2H]-198.832859911
AllCCS[M+HCOO]-199.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
RaltitrexedCN(CC1=CC2=C(NC(C)=NC2=O)C=C1)C1=CC=C(S1)C(=O)N[C@@H](CCC(O)=O)C(O)=O4769.2Standard polar33892256
RaltitrexedCN(CC1=CC2=C(NC(C)=NC2=O)C=C1)C1=CC=C(S1)C(=O)N[C@@H](CCC(O)=O)C(O)=O2849.0Standard non polar33892256
RaltitrexedCN(CC1=CC2=C(NC(C)=NC2=O)C=C1)C1=CC=C(S1)C(=O)N[C@@H](CCC(O)=O)C(O)=O4544.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Raltitrexed,1TMS,isomer #1CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N[C@@H](CCC(=O)O[Si](C)(C)C)C(=O)O)S3)=CC=C2[NH]14297.5Semi standard non polar33892256
Raltitrexed,1TMS,isomer #2CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N[C@@H](CCC(=O)O)C(=O)O[Si](C)(C)C)S3)=CC=C2[NH]14277.8Semi standard non polar33892256
Raltitrexed,1TMS,isomer #3CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N[C@@H](CCC(=O)O)C(=O)O)S3)=CC=C2N1[Si](C)(C)C4377.9Semi standard non polar33892256
Raltitrexed,1TMS,isomer #4CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N([C@@H](CCC(=O)O)C(=O)O)[Si](C)(C)C)S3)=CC=C2[NH]14237.1Semi standard non polar33892256
Raltitrexed,2TMS,isomer #1CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N[C@@H](CCC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C)S3)=CC=C2[NH]14183.7Semi standard non polar33892256
Raltitrexed,2TMS,isomer #2CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N([C@@H](CCC(=O)O[Si](C)(C)C)C(=O)O)[Si](C)(C)C)S3)=CC=C2[NH]14101.8Semi standard non polar33892256
Raltitrexed,2TMS,isomer #3CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N[C@@H](CCC(=O)O[Si](C)(C)C)C(=O)O)S3)=CC=C2N1[Si](C)(C)C4266.9Semi standard non polar33892256
Raltitrexed,2TMS,isomer #4CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N([C@@H](CCC(=O)O)C(=O)O[Si](C)(C)C)[Si](C)(C)C)S3)=CC=C2[NH]14141.2Semi standard non polar33892256
Raltitrexed,2TMS,isomer #5CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N[C@@H](CCC(=O)O)C(=O)O[Si](C)(C)C)S3)=CC=C2N1[Si](C)(C)C4244.1Semi standard non polar33892256
Raltitrexed,2TMS,isomer #6CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N([C@@H](CCC(=O)O)C(=O)O)[Si](C)(C)C)S3)=CC=C2N1[Si](C)(C)C4182.8Semi standard non polar33892256
Raltitrexed,3TMS,isomer #1CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N([C@@H](CCC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C)S3)=CC=C2[NH]14036.7Semi standard non polar33892256
Raltitrexed,3TMS,isomer #1CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N([C@@H](CCC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C)S3)=CC=C2[NH]13834.0Standard non polar33892256
Raltitrexed,3TMS,isomer #1CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N([C@@H](CCC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C)S3)=CC=C2[NH]14891.3Standard polar33892256
Raltitrexed,3TMS,isomer #2CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N[C@@H](CCC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C)S3)=CC=C2N1[Si](C)(C)C4125.6Semi standard non polar33892256
Raltitrexed,3TMS,isomer #2CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N[C@@H](CCC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C)S3)=CC=C2N1[Si](C)(C)C3837.1Standard non polar33892256
Raltitrexed,3TMS,isomer #2CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N[C@@H](CCC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C)S3)=CC=C2N1[Si](C)(C)C4862.7Standard polar33892256
Raltitrexed,3TMS,isomer #3CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N([C@@H](CCC(=O)O[Si](C)(C)C)C(=O)O)[Si](C)(C)C)S3)=CC=C2N1[Si](C)(C)C4063.7Semi standard non polar33892256
Raltitrexed,3TMS,isomer #3CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N([C@@H](CCC(=O)O[Si](C)(C)C)C(=O)O)[Si](C)(C)C)S3)=CC=C2N1[Si](C)(C)C3884.1Standard non polar33892256
Raltitrexed,3TMS,isomer #3CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N([C@@H](CCC(=O)O[Si](C)(C)C)C(=O)O)[Si](C)(C)C)S3)=CC=C2N1[Si](C)(C)C4944.3Standard polar33892256
Raltitrexed,3TMS,isomer #4CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N([C@@H](CCC(=O)O)C(=O)O[Si](C)(C)C)[Si](C)(C)C)S3)=CC=C2N1[Si](C)(C)C4095.5Semi standard non polar33892256
Raltitrexed,3TMS,isomer #4CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N([C@@H](CCC(=O)O)C(=O)O[Si](C)(C)C)[Si](C)(C)C)S3)=CC=C2N1[Si](C)(C)C3850.5Standard non polar33892256
Raltitrexed,3TMS,isomer #4CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N([C@@H](CCC(=O)O)C(=O)O[Si](C)(C)C)[Si](C)(C)C)S3)=CC=C2N1[Si](C)(C)C4901.7Standard polar33892256
Raltitrexed,4TMS,isomer #1CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N([C@@H](CCC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C)S3)=CC=C2N1[Si](C)(C)C3997.4Semi standard non polar33892256
Raltitrexed,4TMS,isomer #1CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N([C@@H](CCC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C)S3)=CC=C2N1[Si](C)(C)C3759.8Standard non polar33892256
Raltitrexed,4TMS,isomer #1CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N([C@@H](CCC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C)S3)=CC=C2N1[Si](C)(C)C4507.8Standard polar33892256
Raltitrexed,1TBDMS,isomer #1CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N[C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O)S3)=CC=C2[NH]14576.1Semi standard non polar33892256
Raltitrexed,1TBDMS,isomer #2CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N[C@@H](CCC(=O)O)C(=O)O[Si](C)(C)C(C)(C)C)S3)=CC=C2[NH]14551.4Semi standard non polar33892256
Raltitrexed,1TBDMS,isomer #3CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N[C@@H](CCC(=O)O)C(=O)O)S3)=CC=C2N1[Si](C)(C)C(C)(C)C4568.6Semi standard non polar33892256
Raltitrexed,1TBDMS,isomer #4CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N([C@@H](CCC(=O)O)C(=O)O)[Si](C)(C)C(C)(C)C)S3)=CC=C2[NH]14500.8Semi standard non polar33892256
Raltitrexed,2TBDMS,isomer #1CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N[C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)S3)=CC=C2[NH]14641.1Semi standard non polar33892256
Raltitrexed,2TBDMS,isomer #2CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N([C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C)S3)=CC=C2[NH]14584.6Semi standard non polar33892256
Raltitrexed,2TBDMS,isomer #3CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N[C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O)S3)=CC=C2N1[Si](C)(C)C(C)(C)C4667.4Semi standard non polar33892256
Raltitrexed,2TBDMS,isomer #4CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N([C@@H](CCC(=O)O)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)S3)=CC=C2[NH]14589.9Semi standard non polar33892256
Raltitrexed,2TBDMS,isomer #5CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N[C@@H](CCC(=O)O)C(=O)O[Si](C)(C)C(C)(C)C)S3)=CC=C2N1[Si](C)(C)C(C)(C)C4638.4Semi standard non polar33892256
Raltitrexed,2TBDMS,isomer #6CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N([C@@H](CCC(=O)O)C(=O)O)[Si](C)(C)C(C)(C)C)S3)=CC=C2N1[Si](C)(C)C(C)(C)C4601.4Semi standard non polar33892256
Raltitrexed,3TBDMS,isomer #1CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N([C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)S3)=CC=C2[NH]14651.0Semi standard non polar33892256
Raltitrexed,3TBDMS,isomer #1CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N([C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)S3)=CC=C2[NH]14308.0Standard non polar33892256
Raltitrexed,3TBDMS,isomer #1CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N([C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)S3)=CC=C2[NH]14942.6Standard polar33892256
Raltitrexed,3TBDMS,isomer #2CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N[C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)S3)=CC=C2N1[Si](C)(C)C(C)(C)C4691.6Semi standard non polar33892256
Raltitrexed,3TBDMS,isomer #2CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N[C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)S3)=CC=C2N1[Si](C)(C)C(C)(C)C4297.4Standard non polar33892256
Raltitrexed,3TBDMS,isomer #2CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N[C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)S3)=CC=C2N1[Si](C)(C)C(C)(C)C4901.0Standard polar33892256
Raltitrexed,3TBDMS,isomer #3CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N([C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C)S3)=CC=C2N1[Si](C)(C)C(C)(C)C4652.4Semi standard non polar33892256
Raltitrexed,3TBDMS,isomer #3CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N([C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C)S3)=CC=C2N1[Si](C)(C)C(C)(C)C4306.6Standard non polar33892256
Raltitrexed,3TBDMS,isomer #3CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N([C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C)S3)=CC=C2N1[Si](C)(C)C(C)(C)C4947.5Standard polar33892256
Raltitrexed,3TBDMS,isomer #4CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N([C@@H](CCC(=O)O)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)S3)=CC=C2N1[Si](C)(C)C(C)(C)C4652.4Semi standard non polar33892256
Raltitrexed,3TBDMS,isomer #4CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N([C@@H](CCC(=O)O)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)S3)=CC=C2N1[Si](C)(C)C(C)(C)C4279.9Standard non polar33892256
Raltitrexed,3TBDMS,isomer #4CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N([C@@H](CCC(=O)O)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)S3)=CC=C2N1[Si](C)(C)C(C)(C)C4927.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Raltitrexed GC-MS (Non-derivatized) - 70eV, Positivesplash10-03dl-2443900000-4123f916ebf757efa4902017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Raltitrexed GC-MS (2 TMS) - 70eV, Positivesplash10-00dr-7321290000-bce279f690f228594cb42017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Raltitrexed GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Raltitrexed , positive-QTOFsplash10-03k9-0709000000-b0a922c0009fee3498632017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Raltitrexed 35V, Positive-QTOFsplash10-0229-0905000000-8495738b2ade19f86c552021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Raltitrexed 35V, Negative-QTOFsplash10-0a4i-0141900000-ff3efc6165c65f4a90242021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Raltitrexed 10V, Positive-QTOFsplash10-074l-0512900000-f514d4a6b300e1598c102016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Raltitrexed 20V, Positive-QTOFsplash10-0h90-0932200000-df9ed4d0d58576d2bb3f2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Raltitrexed 40V, Positive-QTOFsplash10-00di-0910000000-639daf8403905e6f11082016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Raltitrexed 10V, Negative-QTOFsplash10-001i-0290000000-b82035dbae7250dd815a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Raltitrexed 20V, Negative-QTOFsplash10-0bvj-0695700000-22b802197672293574e82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Raltitrexed 40V, Negative-QTOFsplash10-0r09-6940000000-c21b12820e7259aeaa792016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Raltitrexed 10V, Positive-QTOFsplash10-0a4i-0002900000-ab80ccf8854a5fa05e392021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Raltitrexed 20V, Positive-QTOFsplash10-03di-0309000000-662b7467b152c14db8782021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Raltitrexed 40V, Positive-QTOFsplash10-03nc-0964000000-03c9a6de56b48b2a54302021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Raltitrexed 10V, Negative-QTOFsplash10-0671-0294800000-11e71794a8ea129032102021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Raltitrexed 20V, Negative-QTOFsplash10-004j-2839600000-da164ebd563c294893c22021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Raltitrexed 40V, Negative-QTOFsplash10-066r-1893200000-ac9baba8ea2c00c973002021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00293 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00293 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00293
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID94568
KEGG Compound IDC11372
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkRaltitrexed
METLIN IDNot Available
PubChem Compound104758
PDB IDD16
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in tetrahydrofolylpolyglutamate synthase activity
Specific function:
Catalyzes conversion of folates to polyglutamate derivatives allowing concentration of folate compounds in the cell and the intracellular retention of these cofactors, which are important substrates for most of the folate-dependent enzymes that are involved in one-carbon transfer reactions involved in purine, pyrimidine and amino acid synthesis. Unsubstitued reduced folates are the preferred substrates. Metabolizes methotrexate (MTX) to polyglutamates.
Gene Name:
FPGS
Uniprot ID:
Q05932
Molecular weight:
59173.37
References
  1. Innocenti F, Ratain MJ: Update on pharmacogenetics in cancer chemotherapy. Eur J Cancer. 2002 Mar;38(5):639-44. [PubMed:11916544 ]
General function:
Involved in thymidylate synthase activity
Specific function:
Contributes to the de novo mitochondrial thymidylate biosynthesis pathway.
Gene Name:
TYMS
Uniprot ID:
P04818
Molecular weight:
35715.65
References
  1. Yin MB, Guo B, Panadero A, Frank C, Wrzosek C, Slocum HK, Rustum YM: Cyclin E-cdk2 activation is associated with cell cycle arrest and inhibition of DNA replication induced by the thymidylate synthase inhibitor Tomudex. Exp Cell Res. 1999 Feb 25;247(1):189-99. [PubMed:10047461 ]
  2. Cao S, McGuire JJ, Rustum YM: Antitumor activity of ZD1694 (tomudex) against human head and neck cancer in nude mouse models: role of dosing schedule and plasma thymidine. Clin Cancer Res. 1999 Jul;5(7):1925-34. [PubMed:10430100 ]
  3. Ferguson PJ, Collins O, Dean NM, DeMoor J, Li CS, Vincent MD, Koropatnick J: Antisense down-regulation of thymidylate synthase to suppress growth and enhance cytotoxicity of 5-FUdR, 5-FU and Tomudex in HeLa cells. Br J Pharmacol. 1999 Aug;127(8):1777-86. [PubMed:10482907 ]
  4. Orlandi L, Bearzatto A, Abolafio G, De Marco C, Daidone MG, Zaffaroni N: Involvement of bcl-2 and p21waf1 proteins in response of human breast cancer cell clones to Tomudex. Br J Cancer. 1999 Sep;81(2):252-60. [PubMed:10496350 ]
  5. Grem JL, Sorensen JM, Cullen E, Takimoto CH, Steinberg SM, Chen AP, Hamilton JM, Arbuck SG, McAtee N, Lawrence D, Goldspiel B, Johnston PG, Allegra CJ: A Phase I study of raltitrexed, an antifolate thymidylate synthase inhibitor, in adult patients with advanced solid tumors. Clin Cancer Res. 1999 Sep;5(9):2381-91. [PubMed:10499608 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  7. Yang Z, Waldman AS, Wyatt MD: DNA damage and homologous recombination signaling induced by thymidylate deprivation. Biochem Pharmacol. 2008 Oct 15;76(8):987-96. doi: 10.1016/j.bcp.2008.08.010. Epub 2008 Aug 19. [PubMed:18773878 ]
  8. Chen VJ, Bewley JR, Andis SL, Schultz RM, Iversen PW, Shih C, Mendelsohn LG, Seitz DE, Tonkinson JL: Cellular pharmacology of MTA: a correlation of MTA-induced cellular toxicity and in vitro enzyme inhibition with its effect on intracellular folate and nucleoside triphosphate pools in CCRF-CEM cells. Semin Oncol. 1999 Apr;26(2 Suppl 6):48-54. [PubMed:10598555 ]
  9. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]