CL9

2-chloro-2'-deoxyadenosine

Created:	2008-02-18
Last modified:	2011-06-04

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2 entries where CL9 is found as a standalone ligand

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Chemical Details
Formal Charge	0
Atom Count	31
Chiral Atom Count	3
Bond Count	33
Aromatic Bond Count	10

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Chemical Component Summary
Name	2-chloro-2'-deoxyadenosine
Systematic Name (OpenEye OEToolkits)	(2R,3S,5R)-5-(6-amino-2-chloro-purin-9-yl)-2-(hydroxymethyl)oxolan-3-ol
Formula	C₁₀ H₁₂ Cl N₅ O₃
Molecular Weight	285.687
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	10.04	Clc1nc(c2ncn(c2n1)C3OC(C(O)C3)CO)N
SMILES	CACTVS	3.341	Nc1nc(Cl)nc2n(cnc12)[CH]3C[CH](O)[CH](CO)O3
SMILES	OpenEye OEToolkits	1.5.0	c1nc2c(nc(nc2n1C3CC(C(O3)CO)O)Cl)N
Canonical SMILES	CACTVS	3.341	Nc1nc(Cl)nc2n(cnc12)[C@H]3C[C@H](O)[C@@H](CO)O3
Canonical SMILES	OpenEye OEToolkits	1.5.0	c1nc2c(nc(nc2n1[C@H]3C[C@@H]([C@H](O3)CO)O)Cl)N
InChI	InChI	1.03	InChI=1S/C10H12ClN5O3/c11-10-14-8(12)7-9(15-10)16(3-13-7)6-1-4(18)5(2-17)19-6/h3-6,17-18H,1-2H2,(H2,12,14,15)/t4-,5+,6+/m0/s1
InChIKey	InChI	1.03	PTOAARAWEBMLNO-KVQBGUIXSA-N

Drug Info: DrugBank

DrugBank ID	DB00242
Name	Cladribine
Groups	approved investigational
Description	An antineoplastic agent used in the treatment of lymphoproliferative diseases including hairy-cell leukemia.
Synonyms	2-Chloro-2'-deoxyadenosine (2R,3S,5R)-5-(6-amino-2-chloropurin-9-yl)-2-(hydroxymethyl)oxolan-3-ol Cladribinum 2-chloro-deoxyadenosine 2-Chlorodeoxyadenosine 2ClAdo 2-chloro-6-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)purine Cladribine CldAdo 2-Chloro-2'-deoxy-beta-adenosine Cladribina 2-CdA
Brand Names	Litak Cladribine Leustatin Leustatin 1mg/ml Cladribine Injection Mavenclad
Indication	For the treatment of active hairy cell leukemia (leukemic reticuloendotheliosis) as defined by clinically significant anemia, neutropenia, thrombocytopenia, or disease-related symptoms. Also used as an alternative agent for the treatment of chronic lymphocytic leukemia (CLL), low-grade non-Hodgkin's lymphoma, and cutaneous T-cell lymphoma.
Categories	2-Chloroadenosine Agents Causing Muscle Toxicity Antimetabolites Antineoplastic Agents Antineoplastic and Immunomodulating Agents BCRP/ABCG2 Substrates Cardiotoxic antineoplastic agents Deoxyadenosines Deoxyribonucleosides Heterocyclic Compounds, Fused-Ring Immunologic Factors Immunosuppressive Agents Myelosuppressive Agents Narrow Therapeutic Index Drugs Nucleic Acids, Nucleotides, and Nucleosides Nucleosides Purine Analogues Purine Antimetabolite Purine Nucleosides Purines Ribonucleosides Selective Immunosuppressants
ATC-Code	L04AA40 L01BB04
CAS number	4291-63-8

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
Ribonucleoside-diphosphate reductase large subunit	MHVIKRDGRQERVMFDKITSRIQKLCYGLNMDFVDPAQITMKVIQGLYSG...	unknown	inhibitor
Ribonucleoside-diphosphate reductase subunit M2	MLSLRVPLAPITDPQQLQLSPLKGLSLVDKENTPPALSGTRVLASKTARR...	unknown	inhibitor
Ribonucleoside-diphosphate reductase subunit M2 B	MGDPERPEAAGLDQDERSSSDTNESEIKSNEEPLLRKSSRRFVIFPIQYP...	unknown	inhibitor
DNA	-	unknown	other/unknown
DNA polymerase alpha catalytic subunit	MAPVHGDDSLSDSGSFVSSRARREKKSKKGRQEALERLKKAKAGEKYKYE...	unknown	inhibitor
DNA polymerase epsilon catalytic subunit A	MSLRSGGRRRADPGADGEASRDDGATSSVSALKRLERSQWTDKMDLRFGF...	unknown	inhibitor
DNA polymerase epsilon subunit 2	MAPERLRSRALSAFKLRGLLLRGEAIKYLTEALQSISELELEDKLEKIIN...	unknown	inhibitor
DNA polymerase epsilon subunit 3	MAERPEDLNLPNAVITRIIKEALPDGVNISKEARSAISRAASVFVLYATS...	unknown	inhibitor
DNA polymerase epsilon subunit 4	MAAAAAAGSGTPREEEGPAGEAAASQPQAPTSVPGARLSRLPLARVKALV...	unknown	inhibitor
Purine nucleoside phosphorylase	MENGYTYEDYKNTAEWLLSHTKHRPQVAIICGSGLGGLTDKLTQAQIFDY...	unknown	inducer
Deoxycytidine kinase	MATPPKRSCPSFSASSEGTRIKKISIEGNIAAGKSTFVNILKQLCEDWEV...	unknown	substrate
ATP-binding cassette sub-family G member 2	MSSSNVEVFIPVSQGNTNGFPATASNDLKAFTEGAVLSFHNICYRVKLKS...	unknown	substrate
Solute carrier family 28 member 3	MELRSTAAPRAEGYSNVGFQNEENFLENENTSGNNSIRSRAVQSREHTNT...	unknown
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Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682