Nelarabine - Moligand™, ≥98% , DNA inhibitor, CAS No.121032-29-9, DNA inhibitor

CAS: 121032-29-9 Cat. No.: N127709 Molecular Weight: 297.27 EC Number: 642-916-9

GRADE & PURITY Moligand™, ≥98%

Synonyms

506U78 | Arranon | GW 506U78 | Nelzarabine | 9beta-D-Arabinofuranosyl-6-methoxy-9H-purin-2-amine | 9-(β-D-Arabinofuranosyl)-6-methoxy-9H-purin-2-amine | (2R,3S,4S,5R)-2-(2-amino-6-methoxypurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol

Storage

Protected from light,Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Overview

Nelarabine is a purine nucleoside analog and DNA synthesis inhibitor with IC50 from 0.067-2.15 μM in tumor cells.

Nelarabine (arranon, 506U78) is a purine nucleotide analog, which is an inhibitor of DNA synthesis, with an IC50 of 0.067-2.15 for tumor cells μ M. It can act on T cells and acute lymphoblastic leukemia.

Specifications

Synonyms

506U78 | Arranon | GW 506U78 | Nelzarabine | 9beta-D-Arabinofuranosyl-6-methoxy-9H-purin-2-amine | 9-(β-D-Arabinofuranosyl)-6-methoxy-9H-purin-2-amine | (2R, 3S, 4S, 5R)-2-(2-amino-6-methoxypurin-9-yl)-5-(hydroxymethyl)oxolane-3, 4-diol

Specifications & Purity

Moligand™, ≥98%

Biochemical and Physiological Mechanisms

Nucleoside analog. Metabolized by adenosine deaminase to active metabolite, arabinofuranosylguanine (ara-G). Inhibits DNA synthesis and induces apoptosis. Inhibits growth of human T cell lymphoblastic leukemia cellsin vitroandin vivo.

Storage

Protected from light, Store at -20°C, Argon charged

Shipped In

Ice chest + Ice pads

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

Grade

Moligand™

Action Type

INHIBITOR

Mechanism of action

DNA inhibitor

Purity

≥98%

Product Properties

• ALogP: -0.7

Names and Identifiers

• Pubchem Sid: 504762289
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504762289
• Canonical Smiles: COC1=NC(=NC2=C1N=CN2C3C(C(C(O3)CO)O)O)N
• IUPAC Name: (2R,3S,4S,5R)-2-(2-amino-6-methoxypurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• InChIKey: IXOXBSCIXZEQEQ-UHTZMRCNSA-N
• INCHI: 1S/C11H15N5O5/c1-20-9-5-8(14-11(12)15-9)16(3-13-5)10-7(19)6(18)4(2-17)21-10/h3-4,6-7,10,17-19H,2H2,1H3,(H2,12,14,15)/t4-,6-,7+,10-/m1/s1
• Isomeric SMILES: COC1=NC(=NC2=C1N=CN2[C@H]3[C@H]([C@@H]([C@H](O3)CO)O)O)N
• Molecular Weight: 297.27
• Reaxy-Rn: 841479
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=841479&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Nucleosides, nucleotides, and analogues
    • Class Purine nucleosides

• Kingdom: Organic compounds
• Superclass: Nucleosides, nucleotides, and analogues
• Class: Purine nucleosides
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Purine nucleosides
• Alternative Parents: Glycosylamines Pentoses Hypoxanthines Aminopyrimidines and derivatives Alkyl aryl ethers N-substituted imidazoles Tetrahydrofurans Heteroaromatic compounds Secondary alcohols Oxacyclic compounds Azacyclic compounds Primary amines Primary alcohols Organopnictogen compounds Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Purine nucleoside - Glycosyl compound - N-glycosyl compound - Hypoxanthine - Pentose monosaccharide - Purine - Imidazopyrimidine - Aminopyrimidine - Alkyl aryl ether - Pyrimidine - Monosaccharide - N-substituted imidazole - Heteroaromatic compound - Azole - Tetrahydrofuran - Imidazole - Secondary alcohol - Oxacycle - Azacycle - Organoheterocyclic compound - Ether - Organopnictogen compound - Alcohol - Organic oxygen compound - Organic nitrogen compound - Hydrocarbon derivative - Amine - Primary amine - Primary alcohol - Organooxygen compound - Organonitrogen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as purine nucleosides. These are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety.
• External Descriptors: purine nucleoside - monosaccharide derivative - beta-D-arabinoside

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

Associated Targets(Human)

Homo sapiens (32628 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CCRF-HSB-2 (188 Activities)

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THP-1 (11052 Activities)

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Jurkat (10389 Activities)

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ABCC2 Tchem Canalicular multispecific organic anion transporter 1 (1191 Activities)

Discover Target: ABCC2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ABCB11 Tchem Bile salt export pump (2311 Activities)

Discover Target: ABCB11

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ABCC3 Tbio Canalicular multispecific organic anion transporter 2 (718 Activities)

Discover Target: ABCC3

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)

Discover Target: TDP1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ABCC4 Tchem Multidrug resistance-associated protein 4 (785 Activities)

Discover Target: ABCC4

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Associated Targets(non-human)

Hdac6 Histone deacetylase 6 (222 Activities)

Discover Target: Hdac6

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rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: Solvent:DMSO, Max Conc. mg/mL: 29.73, Max Conc. mM: 100; Solvent:water, Max Conc. mg/mL: 2.97, Max Conc. mM: 10 with gentle warming
• Sensitivity: light sensitive;Moisture sensitive;heat sensitive
• Molecular Weight: 297.270 g/mol
• XLogP3: -0.700
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 3
• Exact Mass: 297.107 Da
• Monoisotopic Mass: 297.107 Da
• Topological Polar Surface Area: 149.000 Ų
• Heavy Atom Count: 21
• Formal Charge: 0
• Complexity: 377.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 4
• 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. Kangkang Wang, Yuli Kou, Meng Wang, Xin Ma, Jide Wang.  (2020)  Determination of Nitrofuran Metabolites in Fish by Ultraperformance Liquid Chromatography-Photodiode Array Detection with Thermostatic Ultrasound-Assisted Derivatization.  ACS Omega,      [PMID:32775890] [10.1021/acsomega.0c02068]