Navigation

name Structure Reference Source Properties Activities Metabolism

(2R,3R,4S,5R)-2-(6-amino-2-chloro-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol

AlkaPlorer ID: AK016811

Synonym: '9.beta.-D-Arabinofuranosyl-2-chloroadenine', 'SMR001559917', 'MLS002693982'

IUPAC Name: (2R,3R,4S,5R)-2-(6-amino-2-chloropurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol

Structure

SMILES: NC1=NC(Cl)=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O

copy

InChI: InChI=1S/C10H12ClN5O4/c11-10-14-7(12)4-8(15-10)16(2-13-4)9-6(19)5(18)3(1-17)20-9/h2-3,5-6,9,17-19H,1H2,(H2,12,14,15)/t3-,5-,6-,9-/m1/s1

copy

InChIKey: BIXYYZIIJIXVFW-UUOKFMHZSA-N

copy

Reference

PubChem CID: 8974

CAS: 103090-47-7

SuperNatural Ⅲ: SN0026834-04

NPASS: NPC269827

Properties Information

Molecule Weight: 301.69

TPSA？: 139.54000000000002

MolLogP？: -1.326600000000001

Number of H-Donors: 4

Number of H-Acceptors: 9

RingCount: 3

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Acinetobacter baumannii Acinetobacter baumannii Inhibition 9.97 % 10.6019/CHEMBL4513141
Bos taurus Adenosine A1 receptor Ki 20.2 nM 10.1021/jm9707737
Bos taurus Adenosine A1 receptor Ki 25.0 nM 10.1021/jm00345a001
Bos taurus Adenosine deaminase Ki 54500.0 nM 10.1021/jm101286g
Candida albicans Candida albicans Inhibition 4.78 % 10.6019/CHEMBL4513141
Cavia porcellus Adenosine A1 receptor EC50 190.55 nM 10.1021/jm00108a014
Cavia porcellus Adenosine A2a receptor EC50 8000.0 nM 10.1021/jm00382a018
Cavia porcellus Adenosine A2a receptor Ki 8.0 nM 10.1021/jm00345a001
Cryptococcus neoformans Cryptococcus neoformans Inhibition 0.98 % 10.6019/CHEMBL4513141
Escherichia coli Escherichia coli Inhibition 3.01 % 10.6019/CHEMBL4513141
Escherichia coli K-12 Beta-lactamase AmpC Potency 70794.6 nM None
Homo sapiens Adenosine A1 receptor Activity 90.0 % 10.1021/np50094a001
Homo sapiens Adenosine A1 receptor Affinity constant 0.01 uM 10.1021/jm00345a001
Homo sapiens Adenosine A1 receptor Ki 1.39 nM 10.1021/jm4011669
Homo sapiens Adenosine A1 receptor Ki 2.8 nM 10.1021/acs.jmedchem.6b01183
Homo sapiens Adenosine A1 receptor Ki 18.4 nM 10.1021/np50094a001
Homo sapiens Adenosine A2a receptor Ki 120.0 nM 10.1021/jm9707737
Homo sapiens Adenosine A2a receptor Ki 180.0 nM 10.1021/jm4011669
Homo sapiens Adenosine A2b receptor Activity -0.889 None 10.1021/jm701442d
Homo sapiens Adenosine A2b receptor EC50 nan None 10.1021/jm4011669
Homo sapiens Adenosine A2b receptor Ki 21400.0 nM 10.1021/jm900413e
Homo sapiens Adenosine A2b receptor Ki 25500.0 nM 10.1021/jm900413e
Homo sapiens Adenosine A2b receptor logEC50 -3.724 None 10.1021/jm701442d
Homo sapiens Adenosine A2 receptor Affinity constant 5.0 uM 10.1021/jm00345a001
Homo sapiens Adenosine A2 receptor EC50 25.12 nM 10.1021/jm00108a014
Homo sapiens Adenosine A3 receptor EC50 1630.0 nM 10.1021/jm020211+
Homo sapiens Adenosine A3 receptor Efficacy 100.0 % 10.1021/jm020211+
Homo sapiens Adenosine A3 receptor Ki 19.0 nM 10.1021/jm4011669
Homo sapiens Adenosine A3 receptor Ki 87.0 nM 10.1021/jm020211+
Homo sapiens Adenosine A3 receptor Ki 650.0 nM 10.1021/jm010232o
Homo sapiens Adenosine A3 receptor Ki 11600.0 nM 10.1021/jm010232o
Homo sapiens Adenosine receptor Affinity constant nan None 10.1021/jm00345a001
Homo sapiens Adenosine receptors; A1 & A2 Ratio 9.1 None 10.1021/jm00108a014
Homo sapiens Ataxin-2 Potency 28183.8 nM None
Homo sapiens CCRF-CEM IC50 10000.0 nM 10.1021/jm00080a029
Homo sapiens Cellular tumor antigen p53 Potency 15848.9 nM None
Homo sapiens Cellular tumor antigen p53 Potency 19952.6 nM None
Homo sapiens DNA-(apurinic or apyrimidinic site) lyase Potency 5011.9 nM None
Homo sapiens DNA-(apurinic or apyrimidinic site) lyase Potency 31622.8 nM None
Homo sapiens DNA polymerase iota Potency 25118.9 nM None
Homo sapiens Endoplasmin Kd 8600.0 nM 10.1021/acsmedchemlett.0c00509
Homo sapiens Endoplasmin Ki 1800.0 nM 10.1021/acsmedchemlett.0c00509
Homo sapiens Eukaryotic translation initiation factor 2-alpha kinase 3 EC50 55700.0 nM None
Homo sapiens Flap endonuclease 1 Potency 8436.8 nM None
Homo sapiens Geminin Potency 29092.9 nM None
Homo sapiens Glucagon-like peptide 1 receptor Potency 7079.5 nM None
Homo sapiens Heat shock protein HSP 90-alpha IC50 1250000.0 nM 10.1021/acs.jmedchem.7b01066
Homo sapiens Heat shock protein HSP 90-alpha Inhibition 45.0 % 10.1021/acs.jmedchem.7b01066
Homo sapiens Heat shock protein HSP 90-alpha Kd 38000.0 nM 10.1021/acsmedchemlett.0c00509
Homo sapiens Heat shock protein HSP 90-alpha Ki 2200.0 nM 10.1021/acsmedchemlett.0c00509
Homo sapiens HEK293 Potency 29092.9 nM None
Homo sapiens HEp-2 IC50 3000.0 nM 10.1021/jm00080a029
Homo sapiens HepG2 Potency 35481.3 nM None
Homo sapiens High-affinity choline transporter IC50 335.52 nM None
Homo sapiens High-affinity choline transporter IC50 739.9 nM None
Homo sapiens Histone deacetylase 6 Inhibition -11.41 % 10.6019/CHEMBL4808148
Homo sapiens Histone deacetylase 6 Inhibition 0.98 % 10.6019/CHEMBL4808148
Homo sapiens HT-29 IC50 85600.0 nM 10.1021/jm048944c
Homo sapiens Hypoxia-inducible factor 1 alpha Potency 6309.6 nM None
Homo sapiens Isocitrate dehydrogenase [NADP] cytoplasmic Potency 18356.4 nM None
Homo sapiens K562 IC50 15400.0 nM 10.1021/jm048944c
Homo sapiens K562 IC50 19500.0 nM 10.1021/jm048944c
Homo sapiens MAP kinase ERK2 Potency 10000.0 nM None
Homo sapiens MAP kinase ERK2 Potency 14125.4 nM None
Homo sapiens MCF7 IC50 72600.0 nM 10.1021/jm048944c
Homo sapiens microRNA 21 Potency 116.7 nM None
Homo sapiens Mothers against decapentaplegic homolog 3 Potency 22387.2 nM None
Homo sapiens Nuclear factor erythroid 2-related factor 2 Potency 20596.2 nM None
Homo sapiens Phosphodiesterase 2A IC50 10000.0 nM 10.1016/j.bmc.2017.11.022
Homo sapiens Phosphodiesterase 2A Inhibition 1.83 % 10.1016/j.bmc.2017.11.022
Homo sapiens Prelamin-A/C Potency 10000.0 nM None
Homo sapiens Prelamin-A/C Potency 35481.3 nM None
Homo sapiens Relaxin receptor 1 Potency 2181.0 nM None
Homo sapiens Relaxin receptor 1 Potency 3981.1 nM None
Homo sapiens Relaxin receptor 1 Potency 21810.3 nM None
Homo sapiens Relaxin receptor 2 Potency 17324.5 nM None
Homo sapiens Serotonin 1a (5-HT1a) receptor Inhibition 50.0 % 10.1021/acs.jmedchem.6b01183
Homo sapiens Serotonin 1b (5-HT1b) receptor Inhibition 50.0 % 10.1021/acs.jmedchem.6b01183
Homo sapiens Serotonin 1d (5-HT1d) receptor Inhibition 50.0 % 10.1021/acs.jmedchem.6b01183
Homo sapiens Serotonin 1e (5-HT1e) receptor Inhibition 50.0 % 10.1021/acs.jmedchem.6b01183
Homo sapiens Serotonin 2a (5-HT2a) receptor Inhibition 46.0 % 10.1021/acs.jmedchem.6b01183
Homo sapiens Serotonin 2a (5-HT2a) receptor Ki 10000.0 nM 10.1021/acs.jmedchem.6b01183
Homo sapiens Serotonin 2b (5-HT2b) receptor Inhibition 10.0 % 10.1021/acs.jmedchem.6b01183
Homo sapiens Serotonin 2c (5-HT2c) receptor Inhibition 10.0 % 10.1021/acs.jmedchem.6b01183
Homo sapiens Serotonin 3a (5-HT3a) receptor Inhibition 50.0 % 10.1021/acs.jmedchem.6b01183
Homo sapiens Serotonin 4 (5-HT4) receptor Inhibition 50.0 % 10.1021/acs.jmedchem.6b01183
Homo sapiens Serotonin 5a (5-HT5a) receptor Inhibition 50.0 % 10.1021/acs.jmedchem.6b01183
Homo sapiens Serotonin 6 (5-HT6) receptor Inhibition 50.0 % 10.1021/acs.jmedchem.6b01183
Homo sapiens Serotonin 7 (5-HT7) receptor Inhibition 50.0 % 10.1021/acs.jmedchem.6b01183
Homo sapiens Sodium channel alpha subunits; brain (Types I, II, III) Inhibition 1.3 % 10.1021/jm00381a019
Homo sapiens Sodium channel alpha subunits; brain (Types I, II, III) Inhibition 3.5 % 10.1021/jm00381a019
Homo sapiens Survival motor neuron protein Potency 35481.3 nM None
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 1032.3 nM None
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 1158.2 nM None
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 3662.6 nM None
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 4109.5 nM None
Homo sapiens Vasopressin V1b receptor Potency 19438.4 nM None
Klebsiella pneumoniae Klebsiella pneumoniae Inhibition 2.26 % 10.6019/CHEMBL4513141
Mus musculus L1210 IC50 3000.0 nM 10.1021/jm00080a029
Photinus pyralis Luciferin 4-monooxygenase EC50 112219.0 nM None
Plasmodium falciparum Plasmodium falciparum IC37 11.0 uM 10.1021/acs.jmedchem.9b00182
Plasmodium falciparum Plasmodium falciparum IC50 6309.57 nM 10.1038/nchembio.215
Plasmodium falciparum Plasmodium falciparum IC50 7943.28 nM 10.1038/nchembio.215
Plasmodium falciparum Plasmodium falciparum IC50 10000.0 nM 10.1038/nchembio.215
Plasmodium falciparum Plasmodium falciparum Potency 6573.3 nM None
Plasmodium falciparum Plasmodium falciparum Potency 9285.0 nM None
Pseudomonas aeruginosa Pseudomonas aeruginosa Inhibition 14.41 % 10.6019/CHEMBL4513141
Rattus norvegicus Adenosine A1 receptor EC25 170.0 nM 10.1021/jm00396a044
Rattus norvegicus Adenosine A1 receptor IC50 37.0 nM 10.1021/jm00112a035
Rattus norvegicus Adenosine A1 receptor Ki 6.7 nM 10.1021/jm0003642
Rattus norvegicus Adenosine A1 receptor Ki 6.7 nM 10.1021/jm00116a007
Rattus norvegicus Adenosine A1 receptor Ki 8.74 nM 10.1021/jm00148a001
Rattus norvegicus Adenosine A1 receptor Ki 9.3 nM 10.1021/jm00007a014
Rattus norvegicus Adenosine A1 receptor Ki 9.3 nM 10.1021/jm00047a018
Rattus norvegicus Adenosine A1 receptor Ki 9.3 nM 10.1021/jm00081a001
Rattus norvegicus Adenosine A1 receptor Ki 9.3 nM 10.1021/jm00100a020
Rattus norvegicus Adenosine A1 receptor Ki 9.3 nM 10.1021/jm00128a002
Rattus norvegicus Adenosine A1 receptor Ki 9.3 nM 10.1021/jm00396a044
Rattus norvegicus Adenosine A2a receptor Ki 63.0 nM 10.1021/jm00007a014
Rattus norvegicus Adenosine A2a receptor Ki 63.0 nM 10.1021/jm00047a018
Rattus norvegicus Adenosine A2a receptor Ki 76.0 nM 10.1021/jm0003642
Rattus norvegicus Adenosine A2a receptor Ki 76.0 nM 10.1021/jm00116a007
Rattus norvegicus Adenosine A2 receptor EC25 13.0 nM 10.1021/jm00396a044
Rattus norvegicus Adenosine A2 receptor IC50 160.0 nM 10.1021/jm00112a035
Rattus norvegicus Adenosine A2 receptor Ki 63.0 nM 10.1021/jm00128a002
Rattus norvegicus Adenosine A2 receptor Ki 63.0 nM 10.1021/jm00396a044
Rattus norvegicus Adenosine A2 receptor Ki 63.1 nM 10.1021/jm00148a001
Rattus norvegicus Adenosine A2 receptor Ratio 63.0 nM 10.1021/jm00081a001
Rattus norvegicus Adenosine A3 receptor Ki 1890.0 nM 10.1021/jm00007a014
Rattus norvegicus Adenosine A3 receptor Ki 1890.0 nM 10.1021/jm00047a018
Rattus norvegicus Adenosine A3 receptor Ki 3200.0 nM 10.1021/jm9707737
Rattus norvegicus Adenosine receptor Ki 1.3 nM 10.1021/jm00345a001
Rattus norvegicus Adenosine receptor Ki 9.0 nM 10.1021/jm00345a001
Rattus norvegicus Adenosine receptor Ki 10.0 nM 10.1021/jm00345a001
Rattus norvegicus Adenosine receptor Ki 920.0 nM 10.1021/jm00345a001
Rattus norvegicus Adenosine receptor A2a and A3 Ratio 0.033 None 10.1021/jm00047a018
Rattus norvegicus Adenosine receptors; A1 & A2 Ratio 0.23 None 10.1021/jm00112a035
Rattus norvegicus Adenosine receptors; A1 & A2 Ratio 6.8 None 10.1021/jm00081a001
Rattus norvegicus Adenosine receptors; A1 & A2 Ratio 6.8 None 10.1021/jm00128a002
Rattus norvegicus Adenosine receptors; A1 & A2 Ratio 6.8 None 10.1021/jm00396a044
Rattus norvegicus Adenosine receptors; A1 & A2 Ratio 7.22 None 10.1021/jm00148a001
Rattus norvegicus Adenosine receptors; A1 & A2a Ratio 1.1 None 10.1021/jm00116a007
Rattus norvegicus Adenosine receptors; A1 & A3 Ratio 0.0049 None 10.1021/jm00047a018
Rattus norvegicus Rattus norvegicus Delta HR -25.0 % 10.1021/jm00112a035
Rattus norvegicus Rattus norvegicus ED25 0.015 mg kg-1 10.1021/jm00112a035
Rattus norvegicus Rattus norvegicus IC50 620.0 nM 10.1021/jm00100a020
Severe acute respiratory syndrome coronavirus 2 Replicase polyprotein 1ab Inhibition -0.3454 % 10.6019/CHEMBL4495564
Severe acute respiratory syndrome coronavirus 2 Replicase polyprotein 1ab Inhibition 21.24 % 10.6019/CHEMBL4495564
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition -0.16 % 10.6019/CHEMBL4495565
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition 0.35 % 10.6019/CHEMBL4495565
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition 72.48 % 10.21203/rs.3.rs-23951/v1
Staphylococcus aureus Staphylococcus aureus Inhibition -10.52 % 10.6019/CHEMBL4513141
None ADMET No. of cells 8.8 % 10.1016/s0960-894x(98)00452-1
None ADMET No. of cells 41.8 % 10.1016/s0960-894x(98)00452-1
None ADMET No. of cells 82.7 % 10.1016/s0960-894x(98)00452-1
None ADMET No. of cells 91.9 % 10.1016/s0960-894x(98)00452-1
None Unchecked EC50 701.0 nM None
None Unchecked IC50 460.0 nM 10.1021/jm00116a007
None Unchecked IC50 126000.0 nM 10.1021/acs.jmedchem.7b01066
None Unchecked Inhibition 1.0 % 10.1021/jm9006356
None Unchecked Inhibition nan % 10.1038/nchembio873
None Unchecked Ki 9650.0 nM 10.1021/jm401530a
None Unchecked Ki 100000.0 nM 10.1021/jm9006356
None Unchecked Potency 366.3 nM None
None Unchecked Potency 920.0 nM None
None Unchecked Potency 4466.8 nM None
None Unchecked Potency 7307.8 nM None
None Unchecked Potency 14125.4 nM None
None Unchecked Potency 20596.2 nM None
None Unchecked Potency 22387.2 nM None
None Unchecked Potency 31622.8 nM None
None Unchecked Potency 35481.3 nM None
None Unchecked Potency 39810.7 nM None
None Unchecked Ratio IC50 10.0 None 10.1021/acs.jmedchem.7b01066
None Unchecked Selectivity 5.9 None 10.1021/jm9707737
None Unchecked Selectivity 26.6 None 10.1021/jm9707737
None Unchecked Selectivity 158.4 None 10.1021/jm9707737
None Unchecked Selectivity Index 4.2 None 10.1021/acsmedchemlett.0c00509

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT021085 Nc1nc(Cl)nc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O>>Nc1nc(Cl)nc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]1O enzymemap_44043