Aminopterin - γ-irradiated, BioReagent, suitable for hybridoma, 50 ×, lyophilized powder , CAS No.54-62-6

CAS: 54-62-6 Cat. No.: A755563 Molecular Weight: 440.41(as Anhydrous) Beilstein Registry Number: 69045 EC Number: 200-209-9

GRADE & PURITY BioReagent, Suitable for hybridoma, γ-irradiated, 50 ×, lyophilized powder

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Aminopterin concentrate supplement for hybridoma cell culture applications.

Specifications

Specifications & Purity

γ-irradiated, BioReagent, suitable for hybridoma, 50 ×, lyophilized powder

Biochemical and Physiological Mechanisms

Folic acid antagonist. Aminopterin is actively transported into cells by the folate transporter. In the cell, it is converted to a high molecular weight polyglutamate metabolite by folylpolyglutamate synthase that, in turn, binds to dihydrofolate reduct

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

BioReagent, Suitable for hybridoma, γ-irradiated

Names and Identifiers

• Canonical Smiles: Nc1nc(N)c2nc(CNc3ccc(cc3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)cnc2n1
• IUPAC Name: (2S)-2-[[4-[(2,4-diaminopteridin-6-yl)methylamino]benzoyl]amino]pentanedioic acid
• InChIKey: TVZGACDUOSZQKY-LBPRGKRZSA-N
• INCHI: 1S/C19H20N8O5/c20-15-14-16(27-19(21)26-15)23-8-11(24-14)7-22-10-3-1-9(2-4-10)17(30)25-12(18(31)32)5-6-13(28)29/h1-4,8,12,22H,5-7H2,(H,25,30)(H,28,29)(H,31,32)(H4,20,21,23,26,27)/t12-/m0/s1
• Isomeric SMILES: C1=CC(=CC=C1C(=O)N[C@@H](CCC(=O)O)C(=O)O)NCC2=CN=C3C(=N2)C(=NC(=N3)N)N
• WGK Germany: 3
• RTECS: MA1050000
• UN Number: 2811
• Packing Group: I
• Molecular Weight: 440.41(as Anhydrous)
• Beilstein: 69045
• Reaxy-Rn: 1096637
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1096637&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Pteridines and derivatives
      • Subclass Pterins and derivatives
        • Level5 Pteroic acids and derivatives
          • Level6 Folic acids and derivatives
            • Level7 Folic acids

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Pteridines and derivatives
• Subclass: Pterins and derivatives
• Intermediate Tree Nodes: Pteroic acids and derivatives - Folic acids and derivatives
• Direct Parent: Folic acids
• Alternative Parents: Glutamic acid and derivatives Hippuric acids N-acyl-alpha amino acids Aminobenzamides Aniline and substituted anilines Benzoyl derivatives Phenylalkylamines Secondary alkylarylamines Aminopyrimidines and derivatives Imidolactams Pyrazines Dicarboxylic acids and derivatives Heteroaromatic compounds Secondary carboxylic acid amides Amino acids Carboxylic acids Azacyclic compounds Primary amines Hydrocarbon derivatives Carbonyl compounds Organic oxides Organopnictogen compounds
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Folic acid - Glutamic acid or derivatives - Hippuric acid or derivatives - Hippuric acid - N-acyl-alpha-amino acid - N-acyl-alpha amino acid or derivatives - Alpha-amino acid or derivatives - Aminobenzamide - Aminobenzoic acid or derivatives - Benzamide - Benzoic acid or derivatives - Benzoyl - Phenylalkylamine - Aniline or substituted anilines - Aminopyrimidine - Aralkylamine - Secondary aliphatic/aromatic amine - Pyrimidine - Pyrazine - Monocyclic benzene moiety - Benzenoid - Imidolactam - Dicarboxylic acid or derivatives - Heteroaromatic compound - Secondary carboxylic acid amide - Amino acid or derivatives - Amino acid - Carboxamide group - Secondary amine - Azacycle - Carboxylic acid derivative - Carboxylic acid - Hydrocarbon derivative - Amine - Organonitrogen compound - Organic oxide - Organic nitrogen compound - Organopnictogen compound - Carbonyl group - Primary amine - Organooxygen compound - Organic oxygen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as folic acids. These are heterocyclic compounds based on the 4-[(pteridin-6-ylmethyl)amino]benzoic acid skeleton conjugated with one or more L-glutamate units.
• External Descriptors: dicarboxylic acid

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Solubility: 10 mL/vial, clear, red (in TC Medium)
• Specific Rotation[α]: 20° (C=1,0.1mol/L NaOH)
• Melt Point(°C): 185-204°C
• Molecular Weight: 440.400 g/mol
• XLogP3: -2.000
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 9
• Exact Mass: 440.156 Da
• Monoisotopic Mass: 440.156 Da
• Topological Polar Surface Area: 219.000 Ų
• Heavy Atom Count: 32
• Formal Charge: 0
• Complexity: 674.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• 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

References

1. Mengru Bai, Qian Shen, Yong Wu, Zhiyuan Ma, Yuqing Wang, Mingyang Chen, Dan Liu, Lin Zhou.  (2024)  Evaluation of transport mechanisms of methotrexate in human choriocarcinoma cell lines by LC-MS/MS.  JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS,      [PMID:38823222] [10.1016/j.jpba.2024.116268]

2. Shengqi Zhang, Qian Yin, Shangwei Zhang, Kyriakos Manoli, Lei Zhang, Xin Yu, Mingbao Feng.  (2022)  Chlorination of methotrexate in water revisited: Deciphering the kinetics, novel reaction mechanisms, and unexpected microbial risks.  WATER RESEARCH,      [PMID:36198210] [10.1016/j.watres.2022.119181]