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Lometrexol - 95%, high purity , CAS No.106400-81-1

COA COA
    Grade & Purity:
  • ≥95%
In stock
Item Number
L650029
Grouped product items
SKU Size
Availability
 Price Qty
L650029-1mg
1mg
Available within 8-12 weeks(?)
Production requires sourcing of materials. We appreciate your patience and understanding.
$275.90
L650029-5mg
5mg
Available within 8-12 weeks(?)
Production requires sourcing of materials. We appreciate your patience and understanding.
$830.90
L650029-10mg
10mg
Available within 8-12 weeks(?)
Production requires sourcing of materials. We appreciate your patience and understanding.
$1,395.90
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Basic Description

Synonyms NCGC00485206-02 | (4-(2-((R)-2-Amino-4-oxo-3,4,5,6,7,8-hexahydropyrido[2,3-d]pyrimidin-6-yl)ethyl)benzoyl)-L-glutamic acid | CCG-222045 | HY-14521 | DB12769 | Lometrexol | L-Glutamic acid, N-[4-[2-[(6R)-2-amino-3,4,5,6,7,8-hexahydro-4-oxopyrido[2,3-d]pyri
Specifications & Purity ≥95%
Biochemical and Physiological Mechanisms Lometrexol (DDATHF), an antipurine antifolate , can inhibit the activity of glycinamide ribonucleotide formyltransferase (GARFT) but do not induce detectable levels of DNA strand breaks. Lometrexol can further inhibit de novo purine synthesis, causing abn
Storage Temp Store at -20°C
Shipped In
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Product Description

Lometrexol (DDATHF), an antipurine antifolate , can inhibit the activity of glycinamide ribonucleotide formyltransferase (GARFT) but do not induce detectable levels of DNA strand breaks. Lometrexol can further inhibit de novo purine synthesis, causing abnormal cell proliferation and apoptosis , even cell cycle arrest. Lometrexol has anticancer activity. Lometrexol also is a potent human Serine hydroxymethyltransferase1/2 ( hSHMT1/2 ) inhibitor .

In Vitro

Lometrexol (DDATHF) binds tightly to GART, resulting in a rapid and prolonged depletion of intracellular purine ribonucleotides. Lometrexol (1-30 μM; 2-10 hours) induces rapid and complete growth inhibition in L1210 cells. Lometrexol (1 μM; 2-24 hours) induces cell cycle arrest in murine leukemia L1210 cells. MCE has not independently confirmed the accuracy of these methods. They are for reference only. Cell Viability AssayCell Line: Mouse leukemia L1210 cells Concentration: 1, 30 μM Incubation Time: 2, 4, 6, 8, 10 hours Result: Induced rapid and complete growth inhibition. Cell Cycle AnalysisCell Line: L1210 cells Concentration: 1 μM Incubation Time: 2, 4, 8, 12, 24 hours Result: Caused a rapid loss of the G2/M phase population of cells and an early S phase accumulation of cells by 8 hours. By 24 h, the S phase population appeared to be slowly shifting to higher DNA content, and hence, from mid-to-late S phase.

In Vivo

Lometrexol (DDATHF; i.p.; 15-60 mg/kg; on gestation day 7.5) induces neural tube defects (NTDs) by disturbing purine metabolism and increases the rate of embryonic resorption and growth retardation in a dose-dependent manner . Lometrexol (i.p.; 40 mg/kg; on gestation day 7.5) decreases glycinamide ribonucleotide formyl transferase (GARFT) activity and Changes of ATP, GTP, dATP and dGTP levels . Lometrexol (i.p.; 40 mg/kg; on gestation day 7.5) induces abnormal proliferation and apoptosis exist in neural tube defects (NTDs) . MCE has not independently confirmed the accuracy of these methods. They are for reference only. Animal Model: C57BL/6 mice (7-8 week, 18-20 g) Dosage: 15, 30, 35, 40, 45 and 60 mg/kg Administration: Intraperitoneal injection; on gestation day 7.5 Result: Increased the rate of embryonic resorption and growth retardation in a dose-dependent manner. Animal Model: C57BL/6 mice (7-8 week, 18-20 g) Dosage: 40 mg/kg Administration: Intraperitoneal injection; on gestation day 7.5, for 0, 6, 24, 48 and 96 hours Result: Inhibited glycinamide ribonucleotide formyl transferase (GARFT) activity and GARFT activity was maximally inhibited after at 6 hours. Decreased the levels of ATP, GTP, dATP, and dGTP of NTDs embryonic brain tissue significantly at 6 hours. Animal Model: C57BL/6 mice (7-8 week, 18-20 g) Dosage: 40 mg/kg Administration: Intraperitoneal injection; on gestation day 7.5, for 4 days Result: Decreased the expression of proliferation-related genes (Pcna, Foxg1 and Ptch1) and increased the expression of apoptosis-related genes (Bax, Casp8 and Casp9) in NTD groups.

Form:Solid

Taxonomic Classification

Taxonomy Tree

Kingdom Organic compounds
Superclass Organic acids and derivatives
Class Carboxylic acids and derivatives
Subclass Amino acids, peptides, and analogues
Intermediate Tree Nodes Amino acids and derivatives - Alpha amino acids and derivatives
Direct Parent Glutamic acid and derivatives
Alternative Parents Hippuric acids  N-acyl-alpha amino acids  Pyridopyrimidines  Benzoyl derivatives  Pyrimidones  Secondary alkylarylamines  Aminopyrimidines and derivatives  Pyridines and derivatives  Dicarboxylic acids and derivatives  Vinylogous amides  Heteroaromatic compounds  Amino acids  Secondary carboxylic acid amides  Azacyclic compounds  Carboxylic acids  Carbonyl compounds  Hydrocarbon derivatives  Organic oxides  Organopnictogen compounds  Primary amines  
Molecular Framework Aromatic heteropolycyclic compounds
Substituents Glutamic acid or derivatives - Hippuric acid or derivatives - Hippuric acid - N-acyl-alpha-amino acid - N-acyl-alpha amino acid or derivatives - Pyridopyrimidine - Benzoic acid or derivatives - Benzamide - Benzoyl - Secondary aliphatic/aromatic amine - Pyrimidone - Aminopyrimidine - Pyrimidine - Dicarboxylic acid or derivatives - Pyridine - Benzenoid - Monocyclic benzene moiety - Heteroaromatic compound - Vinylogous amide - Carboxamide group - Amino acid - Secondary carboxylic acid amide - Azacycle - Carboxylic acid - Organoheterocyclic compound - Secondary amine - Organic nitrogen compound - Amine - Carbonyl group - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organic oxygen compound - Primary amine - Organooxygen compound - Organonitrogen compound - Aromatic heteropolycyclic compound
Description This compound belongs to the class of organic compounds known as glutamic acid and derivatives. These 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.
External Descriptors pyridopyrimidine - N-acyl-L-glutamic acid

Associated Targets(Human)

GART Tclin Trifunctional purine biosynthetic protein adenosine-3 (9 Activities)
Activity Type Activity Value -log(M) Mechanism of Action Activity Reference Publications (PubMed IDs)
FOLR1 Tclin Folate receptor alpha (184 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
SLC19A1 Tchem Folate transporter 1 (134 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
ATIC Tchem AICAR transformylase (241 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
FPGS Tchem Folylpoly-gamma-glutamate synthetase (250 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
GART Tclin GAR transformylase (531 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
FOLR2 Tchem Folate receptor beta (148 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
CCRF-CEM (65223 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
MCF7 (126967 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
MOLT-4 (49676 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
R2 (178 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
IGROV-1 (47897 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
KB (17409 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID

Associated Targets(non-human)

Hdac6 Histone deacetylase 6 (222 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Sus scrofa (849 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
rep Replicase polyprotein 1ab (378 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID

Mechanisms of Action

Mechanism of Action Action Type target ID Target Name Target Type Target Organism Binding Site Name References

Names and Identifiers

IUPAC Name (2S)-2-[[4-[2-[(6R)-2-amino-4-oxo-5,6,7,8-tetrahydro-3H-pyrido[2,3-d]pyrimidin-6-yl]ethyl]benzoyl]amino]pentanedioic acid
INCHI InChI=1S/C21H25N5O6/c22-21-25-17-14(19(30)26-21)9-12(10-23-17)2-1-11-3-5-13(6-4-11)18(29)24-15(20(31)32)7-8-16(27)28/h3-6,12,15H,1-2,7-10H2,(H,24,29)(H,27,28)(H,31,32)(H4,22,23,25,26,30)/t12-,15+/m1/s1
InChIKey ZUQBAQVRAURMCL-DOMZBBRYSA-N
Smiles C1C(CNC2=C1C(=O)NC(=N2)N)CCC3=CC=C(C=C3)C(=O)NC(CCC(=O)O)C(=O)O
Isomeric SMILES C1[C@H](CNC2=C1C(=O)NC(=N2)N)CCC3=CC=C(C=C3)C(=O)N[C@@H](CCC(=O)O)C(=O)O
Alternate CAS 106400-81-1
PubChem CID 135413518
MeSH Entry Terms 5,10-DDTF;5,10-dideaza-5,6,7,8-tetrahydrofolic acid;5,10-dideazatetrahydrofolate;5,10-dideazatetrahydrofolic acid;DDATHF;lometrexol;lometrexol, (6R)-isomer;lometrexol, (6S)-isomer
Molecular Weight 443.5

Certificates（CoA,COO,BSE/TSE and Analysis Chart)

C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:

Chemical and Physical Properties

Solubility DMSO : ≥ 40 mg/mL (90.20 mM)
Molecular Weight 443.500 g/mol
XLogP3 0.300
Hydrogen Bond Donor Count 6
Hydrogen Bond Acceptor Count 8
Rotatable Bond Count 9
Exact Mass 443.18 Da
Monoisotopic Mass 443.18 Da
Topological Polar Surface Area 183.000 Ų
Heavy Atom Count 32
Formal Charge 0
Complexity 831.000
Isotope Atom Count 0
Defined Atom Stereocenter Count 2
Undefined Atom Stereocenter Count 0
Defined Bond Stereocenter Count 0
Undefined Bond Stereocenter Count 0
The total count of all stereochemical bonds 0
Covalently-Bonded Unit Count 1

Solution Calculators

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