9-β-D-Arabinofuranosylguanine Hydrate - Moligand™,≥98% , CAS No.38819-10-2

CAS: 38819-10-2 Cat. No.: B153015 Molecular Weight: 283.24（free basis） EC Number: 815-087-8

GRADE & PURITY Moligand™, ≥98%

Synonyms

A921433 | araG | HMS3263D20 | LP01219 | NSC-76352 | Guanine arabinoside | Guanine, 9-(beta-D-arabinofuranosyl)- | NCGC00261904-01 | Tox21_501219 | 2-amino-9-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-purin-6-one | NYHBQMYGNKIUIF-FJFJXFQ

Storage

Store at 2-8°C,Protected from light

Shipped In

Wet ice

Overview

Ara-G is a deoxyguanosine (GdR) analog and a nucleoside analogue that is rapidly converted by cells of the T lymphoid lineage to its corresponding arabinosylguanine nucleotide triphosphate (araGTP), resulting in inhibition of DNA synthesis and selective in vitro toxicity to T lymphoblastoid cell lines as well as to freshly isolated leukemia cells from patients with T cell acute lymphoblastic leukemia (ALL).

Specifications

Synonyms

A921433 | araG | HMS3263D20 | LP01219 | NSC-76352 | Guanine arabinoside | Guanine, 9-(beta-D-arabinofuranosyl)- | NCGC00261904-01 | Tox21_501219 | 2-amino-9-[(2R, 3S, 4S, 5R)-3, 4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-purin-6-one | NYHBQMYGNKIUIF-FJFJXFQ

Specifications & Purity

Moligand™, ≥98%

Biochemical and Physiological Mechanisms

Nucleoside analog. Converted by cellular kinases to the active 5'-triphosphate (Ara-GTP) and subsequently incorporated into DNA leading to inhibition of DNA synthesis and apoptosis.

Storage

Store at 2-8°C, Protected from light

Shipped In

Wet ice

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

Grade

Moligand™

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥98%

Names and Identifiers

• Canonical Smiles: C1=NC2=C(N1C3C(C(C(O3)CO)O)O)N=C(NC2=O)N
• IUPAC Name: 2-amino-9-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-purin-6-one
• InChIKey: NYHBQMYGNKIUIF-FJFJXFQQSA-N
• INCHI: 1S/C10H13N5O5/c11-10-13-7-4(8(19)14-10)12-2-15(7)9-6(18)5(17)3(1-16)20-9/h2-3,5-6,9,16-18H,1H2,(H3,11,13,14,19)/t3-,5-,6+,9-/m1/s1
• Isomeric SMILES: C1=NC2=C(N1[C@H]3[C@H]([C@@H]([C@H](O3)CO)O)O)N=C(NC2=O)N
• RTECS: MF8301000
• Molecular Weight: 283.24（free basis）
• Reaxy-Rn: 1087986
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1087986&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 Purines and purine derivatives Hydroxypyrimidines N-substituted imidazoles Tetrahydrofurans Heteroaromatic compounds Secondary alcohols Oxacyclic compounds Azacyclic compounds Primary alcohols Organopnictogen compounds Organonitrogen compounds Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Purine nucleoside - Glycosyl compound - N-glycosyl compound - Pentose monosaccharide - Imidazopyrimidine - Purine - Hydroxypyrimidine - Monosaccharide - N-substituted imidazole - Pyrimidine - Heteroaromatic compound - Azole - Imidazole - Tetrahydrofuran - Secondary alcohol - Azacycle - Oxacycle - Organoheterocyclic compound - Primary alcohol - Organopnictogen compound - Organooxygen compound - Organonitrogen compound - Alcohol - Hydrocarbon derivative - Organic oxygen compound - Organic nitrogen 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 - 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)

TK1 Tchem Thymidine kinase, cytosolic (627 Activities)

Discover Target: TK1

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

TK2 Tchem Thymidine kinase, mitochondrial (96 Activities)

Discover Target: TK2

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

Associated Targets(non-human)

TK Thymidine kinase (276 Activities)

Discover Target: TK

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

dnk Deoxynucleoside kinase (95 Activities)

Discover Target: dnk

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

Mechanisms of Action

Chemical and Physical Properties

• Solubility: DMF: 3 mg/ml；DMSO: 5 mg/ml；Ethanol: Partially soluble；PBS (pH 7.2): 0.3 mg/ml
• Sensitivity: Heat Sensitive；light sensitive
• Melt Point(°C): 225°C(lit.)
• Molecular Weight: 283.240 g/mol
• XLogP3: -1.900
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 283.092 Da
• Monoisotopic Mass: 283.092 Da
• Topological Polar Surface Area: 155.000 Ų
• Heavy Atom Count: 20
• Formal Charge: 0
• Complexity: 446.000
• 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