N⁶-Cyclopentyladenosine - Moligand™, ≥98% , Agonist of A 1 receptor;Agonist of A 2A receptor;Agonist of A 2B receptor;Agonist of A 3 receptor, CAS No.41552-82-3, Agonist of A 1 receptor;Agonist of A 2A receptor;Agonist of A 2B receptor;Agonist of A 3 receptor

CAS: 41552-82-3 Cat. No.: N170248 Molecular Weight: 335.36

GRADE & PURITY Moligand™, ≥98%

Synonyms

CPA | HY-103181 | J-523544 | PDSP2_001053 | n-cyclopentyladenosine | n-cyclopentyl-adenosine | NCGC00023909-06 | NCGC00023909-05 | SQMWSBKSHWARHU-SDBHATRESA-N | HMS3412D12 | (2R,3R,4S,5R)-2-(6-(Cyclopentylamino)-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrof

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Specifications

Synonyms

CPA | HY-103181 | J-523544 | PDSP2_001053 | n-cyclopentyladenosine | n-cyclopentyl-adenosine | NCGC00023909-06 | NCGC00023909-05 | SQMWSBKSHWARHU-SDBHATRESA-N | HMS3412D12 | (2R, 3R, 4S, 5R)-2-(6-(Cyclopentylamino)-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrof

Specifications & Purity

Moligand™, ≥98%

Biochemical and Physiological Mechanisms

Potent and selective adenosine A 1 receptor agonist (K i values are 2.3, 790 and 43 nM for human A 1 , A 2A and A 3 receptors, respectively). Centrally active following systemic administration in vivo . Anticonvulsant, with cardiovacular actions, and effe

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

Moligand™

Action Type

AGONIST

Mechanism of action

Agonist of A 1 receptor;Agonist of A 2A receptor;Agonist of A 2B receptor;Agonist of A 3 receptor

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: C1CCC(C1)NC2=C3C(=NC=N2)N(C=N3)C4C(C(C(O4)CO)O)O
• IUPAC Name: (2R,3R,4S,5R)-2-[6-(cyclopentylamino)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol
• InChIKey: SQMWSBKSHWARHU-SDBHATRESA-N
• INCHI: 1S/C15H21N5O4/c21-5-9-11(22)12(23)15(24-9)20-7-18-10-13(16-6-17-14(10)20)19-8-3-1-2-4-8/h6-9,11-12,15,21-23H,1-5H2,(H,16,17,19)/t9-,11-,12-,15-/m1/s1
• Isomeric SMILES: C1CCC(C1)NC2=C3C(=NC=N2)N(C=N3)[C@H]4[C@@H]([C@@H]([C@H](O4)CO)O)O
• WGK Germany: 3
• Molecular Weight: 335.36
• Reaxy-Rn: 7390832
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=7390832&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 6-alkylaminopurines Pentoses Secondary alkylarylamines Aminopyrimidines and derivatives N-substituted imidazoles Imidolactams Tetrahydrofurans Heteroaromatic compounds Secondary alcohols Oxacyclic compounds Azacyclic compounds Primary alcohols Organopnictogen compounds Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Purine nucleoside - Glycosyl compound - N-glycosyl compound - 6-alkylaminopurine - 6-aminopurine - Pentose monosaccharide - Imidazopyrimidine - Purine - Aminopyrimidine - Secondary aliphatic/aromatic amine - Monosaccharide - N-substituted imidazole - Pyrimidine - Imidolactam - Tetrahydrofuran - Azole - Imidazole - Heteroaromatic compound - Secondary alcohol - Organoheterocyclic compound - Azacycle - Secondary amine - Oxacycle - Amine - Organic nitrogen compound - Alcohol - Hydrocarbon derivative - Organopnictogen compound - Organonitrogen compound - Organooxygen compound - Organic oxygen compound - Primary alcohol - 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: Not available

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)

ADORA2A Tclin Adenosine receptor A2a (2 Activities)

Discover Target: ADORA2A

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

ADORA2B Tclin Adenosine receptor A2b (1 Activities)

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Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

ADORA1 Tclin Adenosine receptor A1 (15 Activities)

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Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

ADORA3 Tchem Adenosine receptor A3 (5 Activities)

Discover Target: ADORA3

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

ABL1 Tclin Tyrosine-protein kinase ABL (18331 Activities)

Discover Target: ABL1

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

ADRB2 Tclin Beta-2 adrenergic receptor (11824 Activities)

Discover Target: ADRB2

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

ADRA2A Tclin Alpha-2a adrenergic receptor (9450 Activities)

Discover Target: ADRA2A

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

ADORA1 Tclin Adenosine A1 receptor (17603 Activities)

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

AGTR1 Tclin Type-1 angiotensin II receptor (5176 Activities)

Discover Target: AGTR1

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

ADRA1A Tclin Alpha-1a adrenergic receptor (8359 Activities)

Discover Target: ADRA1A

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

AVPR1B Tclin Vasopressin V1b receptor (1301 Activities)

Discover Target: AVPR1B

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

SLC29A1 Tclin Equilibrative nucleoside transporter 1 (1711 Activities)

Discover Target: SLC29A1

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

ADORA2A Tclin Adenosine A2a receptor (16305 Activities)

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

ADORA2B Tclin Adenosine A2b receptor (7672 Activities)

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

ADORA3 Tchem Adenosine A3 receptor (15931 Activities)

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

GSK3B Tclin Glycogen synthase kinase-3 beta (11785 Activities)

Discover Target: GSK3B

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

CSNK1D Tchem Casein kinase I delta (4546 Activities)

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

GAA Tclin Lysosomal alpha-glucosidase (35701 Activities)

Discover Target: GAA

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

S1PR1 Tclin Sphingosine 1-phosphate receptor Edg-1 (5806 Activities)

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

CDK2 Tchem Cyclin-dependent kinase 2 (9050 Activities)

Discover Target: CDK2

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

GAPDH Tchem Glyceraldehyde-3-phosphate dehydrogenase liver (1284 Activities)

Discover Target: GAPDH

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

GLP1R Tclin Glucagon-like peptide 1 receptor (111429 Activities)

Discover Target: GLP1R

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

C5AR1 Tclin C5a anaphylatoxin chemotactic receptor (2677 Activities)

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

AURKA Tchem Serine/threonine-protein kinase Aurora-A (10240 Activities)

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

Caco-2 (12174 Activities)

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HT-29 (80576 Activities)

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K562 (73714 Activities)

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MCF7 (126967 Activities)

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U2OS (164939 Activities)

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CX3CR1 Tchem C-X3-C chemokine receptor 1 (1686 Activities)

Discover Target: CX3CR1

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

FPR2 Tchem Lipoxin A4 receptor (3472 Activities)

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

FFAR4 Tchem G-protein coupled receptor 120 (2999 Activities)

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

HTT Tchem Huntingtin (19182 Activities)

Discover Target: HTT

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

APEX1 Tchem DNA-(apurinic or apyrimidinic site) lyase (38016 Activities)

Discover Target: APEX1

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

EHMT2 Tchem Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 (93046 Activities)

Discover Target: EHMT2

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

BRD4 Tchem Bromodomain-containing protein 4 (13122 Activities)

Discover Target: BRD4

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

SMAD3 Tchem Mothers against decapentaplegic homolog 3 (68039 Activities)

Discover Target: SMAD3

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

GPR35 Tchem G-protein coupled receptor 35 (2643 Activities)

Discover Target: GPR35

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

RXFP1 Tchem Relaxin receptor 1 (6345 Activities)

Discover Target: RXFP1

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

microRNA 21 (64692 Activities)

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RXFP2 Tbio Relaxin receptor 2 (377 Activities)

Discover Target: RXFP2

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

CBX1 Tbio Chromobox protein homolog 1 (92434 Activities)

Discover Target: CBX1

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

ATAD5 Tbio ATPase family AAA domain-containing protein 5 (122566 Activities)

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

IDH1 Tclin Isocitrate dehydrogenase [NADP] cytoplasmic (40980 Activities)

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

ADORA1 Tclin Adenosine receptors; A1 & A3 (1051 Activities)

Discover Target: ADORA1

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

PGK1 Tchem Phosphoglycerate kinase (287 Activities)

Discover Target: PGK1

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

TRIM24 Tchem Transcription intermediary factor 1-alpha (2087 Activities)

Discover Target: TRIM24

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

BRPF1 Tchem Peregrin (2217 Activities)

Discover Target: BRPF1

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

HEK-293T (167025 Activities)

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ADGRF1 Tbio Adhesion G-protein coupled receptor F1 (1591 Activities)

Discover Target: ADGRF1

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

Associated Targets(non-human)

ampC Beta-lactamase AmpC (62480 Activities)

Discover Target: ampC

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

Aplnr Apelin receptor (201 Activities)

Discover Target: Aplnr

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

Mapk1 MAP kinase ERK2 (650 Activities)

Discover Target: Mapk1

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

Hdac6 Histone deacetylase 6 (222 Activities)

Discover Target: Hdac6

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

Fgfr3 Fibroblast growth factor receptor 3 (21 Activities)

Discover Target: Fgfr3

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

Plasmodium falciparum (966862 Activities)

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Cavia porcellus (23802 Activities)

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Gerbillinae (442 Activities)

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Mus musculus (284745 Activities)

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Rattus norvegicus (775804 Activities)

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H9c2 (3506 Activities)

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ermC' Erythromycin resistance protein (32 Activities)

Discover Target: ermC'

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

rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

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

Gpr119 Glucose-dependent insulinotropic receptor (270 Activities)

Discover Target: Gpr119

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

pfk 6-phospho-1-fructokinase (7870 Activities)

Discover Target: pfk

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

Txnrd1 Thioredoxin reductase 1, cytoplasmic (45279 Activities)

Discover Target: Txnrd1

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

A1 adenosine receptor (82 Activities)

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Adora2b Adenosine A2 receptor (1828 Activities)

Discover Target: Adora2b

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

Adora2b Adenosine receptors; A1 & A2 (886 Activities)

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

Adora1 Adenosine receptors; A1 & A2a (368 Activities)

Discover Target: Adora1

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

Adora2a Adenosine receptor A2a and A3 (172 Activities)

Discover Target: Adora2a

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

SARS-CoV-2 (38078 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: H2O: 1.7 mg/mL 0.1 M HCl: 12 mg/mL DMSO: 23 mg/mL
• Molecular Weight: 335.360 g/mol
• XLogP3: 0.900
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 335.159 Da
• Monoisotopic Mass: 335.159 Da
• Topological Polar Surface Area: 126.000 Ų
• Heavy Atom Count: 24
• Formal Charge: 0
• Complexity: 438.000
• 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. Xiaoxia Tian, Yue Dai, Yuanyuan Cheng, Lingdong Zhang, Rong-Mei Kong, Lian Xia, Cong Kong, Guoliang Li.  (2021)  Combination of pipette tip solid phase extraction and high performance liquid chromatography for determination of plant growth regulators in food samples based on the electrospun covalent organic framework/polyacrylonitrile nanofiber as highly efficient sorbent.  JOURNAL OF CHROMATOGRAPHY A,      [PMID:34883355] [10.1016/j.chroma.2021.462692]

2. Fenglei Gao, Lili Du, Yu Zhang, Fuyi Zhou, Daoquan Tang.  (2016)  A sensitive sandwich-type electrochemical aptasensor for thrombin detection based on platinum nanoparticles decorated carbon nanocages as signal labels.  BIOSENSORS & BIOELECTRONICS,      [PMID:27376191] [10.1016/j.bios.2016.06.055]

3. Jieqiong Qin, Zhiping Du, Xiaoyuan Ma, Yanyan Zhu, Guoyong Wang.  (2015)  Effect of siloxane backbone length on butynediol-ethoxylate based polysiloxanes.  JOURNAL OF MOLECULAR LIQUIDS,      [PMID:] [10.1016/j.molliq.2015.11.058]