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acadesine

AlkaPlorer ID: AK035848

Synonym: None

IUPAC Name: 5-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]imidazole-4-carboxamide

Structure

SMILES: NC(=O)C1=C(N)N([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C=N1

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InChI: InChI=1S/C9H14N4O5/c10-7-4(8(11)17)12-2-13(7)9-6(16)5(15)3(1-14)18-9/h2-3,5-6,9,14-16H,1,10H2,(H2,11,17)/t3-,5-,6-,9-/m1/s1

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InChIKey: RTRQQBHATOEIAF-UUOKFMHZSA-N

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Reference

PubChem CID: 17513

CAS: 2627-69-2

SuperNatural Ⅲ: SN0335034-04

NPASS: NPC188660

Properties Information

Molecule Weight: 258.23400000000004

TPSA？: 156.85000000000002

MolLogP？: -2.8243

Number of H-Donors: 5

Number of H-Acceptors: 8

RingCount: 2

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Felid alphaherpesvirus 1 Felid alphaherpesvirus 1 EC50 100000.0 nM 10.1016/j.ejmech.2013.09.047
Homo sapiens AMP-activated protein kinase, AMPK EC50 nan None 10.1016/j.bmc.2020.115307
Homo sapiens CCRF-CEM IC50 210000.0 nM 10.1016/j.ejmech.2013.09.047
Homo sapiens Glycogen synthase kinase-3 FC 2.0 None 10.1021/acs.jnatprod.8b00079
Homo sapiens HCT-116 Activity nan None 10.1021/acsmedchemlett.2c00196
Homo sapiens HCT-116 EC50 100000.0 nM 10.1021/acsmedchemlett.2c00196
Homo sapiens HEK293 EC50 100000.0 nM 10.1021/acsmedchemlett.2c00196
Homo sapiens HEL MCC 100000.0 nM 10.1016/j.ejmech.2013.09.047
Homo sapiens HeLa IC50 165000.0 nM 10.1016/j.ejmech.2013.09.047
Homo sapiens HeLa IC50 250000.0 nM 10.1016/j.ejmech.2013.09.047
Homo sapiens Histone deacetylase 6 Inhibition 9.36 % 10.6019/CHEMBL4808148
Homo sapiens Histone deacetylase 6 Inhibition 16.58 % 10.6019/CHEMBL4808148
Homo sapiens K562 IC50 800000.0 nM 10.1016/j.bmcl.2018.03.063
Homo sapiens K562 IC50 800000.0 nM 10.1021/acs.jmedchem.6b01803
Homo sapiens K-562R IC50 800000.0 nM 10.1016/j.bmcl.2018.03.063
Homo sapiens MCF7 TGI 42.16 % 10.1039/d0md00051e
Homo sapiens MDA-MB-231 IC50 1000000.0 nM 10.1016/j.bmcl.2017.03.018
Homo sapiens MDA-MB-453 IC50 1700000.0 nM 10.1016/j.bmc.2020.115307
Homo sapiens P-glycoprotein 1 Inhibition nan % 10.1021/acsmedchemlett.2c00196
Homo sapiens RCC4 Activity nan None 10.1016/j.bmcl.2017.03.018
Homo sapiens RCC4 IC50 250000.0 nM 10.1016/j.bmcl.2017.03.018
Homo sapiens SK-BR-3 IC50 180000.0 nM 10.1016/j.bmc.2020.115307
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 70794.6 nM None
Human alphaherpesvirus 1 Human alphaherpesvirus 1 EC50 100000.0 nM 10.1016/j.ejmech.2013.09.047
Human alphaherpesvirus 2 Human alphaherpesvirus 2 EC50 100000.0 nM 10.1016/j.ejmech.2013.09.047
Mus musculus 3T3-L1 Activity nan None 10.1016/j.bmc.2015.05.057
Mus musculus 3T3-L1 Inhibition 50.96 % 10.1016/j.ejmech.2014.09.094
Mus musculus L1210 IC50 250000.0 nM 10.1016/j.ejmech.2013.09.047
Mus musculus Mus musculus Activity nan None 10.1016/j.ejmech.2020.112649
Mus musculus Mus musculus Activity nan None 10.1021/np400867m
Mus musculus Mus musculus Activity_index 3.01 None 10.1016/j.ejmech.2020.112649
Mus musculus Mus musculus Activity_index 8.64 None 10.1016/j.ejmech.2020.112649
Mus musculus Mus musculus Activity_index 15.94 None 10.1016/j.ejmech.2020.112649
Mus musculus Mus musculus Activity_index 20.09 None 10.1016/j.ejmech.2020.112649
Mus musculus Mus musculus Activity_index 57.41 None 10.1016/j.ejmech.2020.112649
Mus musculus Protein-tyrosine phosphatase 1B Inhibition nan % 10.1016/j.bmcl.2017.09.031
Severe acute respiratory syndrome coronavirus 2 Replicase polyprotein 1ab Inhibition 7.481 % 10.6019/CHEMBL4495564
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 IC50 19952.62 nM 10.6019/CHEMBL4651402
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 IC50 20000.0 nM 10.6019/CHEMBL4651402
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition -4.27 % 10.21203/rs.3.rs-23951/v1
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition -0.07 % 10.6019/CHEMBL4495565
None Hepatotoxicity Hepatotoxicity nan None 10.1021/tx900326k
None Molecular identity unknown Activity nan None 10.1016/j.bmc.2015.05.057
None NON-PROTEIN TARGET Potency 0.8 nM None
None NON-PROTEIN TARGET Potency 4.2 nM None
None NON-PROTEIN TARGET Potency 9.4 nM None
None No relevant target solubility nan None 10.1016/j.bmc.2020.115307
None Unchecked Ac50 1.259 uM None
None Unchecked Ac50 7.079 uM None
None Unchecked AC50 1258.9 nM None
None Unchecked AC50 7079.5 nM None
None Unchecked Activity nan None 10.1016/j.bmc.2014.08.037
None Unchecked Activity nan None 10.1016/j.bmc.2015.05.057
None Unchecked Activity nan None 10.1016/j.bmcl.2016.11.034
None Unchecked Activity nan None 10.1016/j.ejmech.2018.01.089
None Unchecked Activity nan None 10.1016/j.ejmech.2020.112172
None Unchecked Activity nan None 10.1016/j.ejmech.2020.112649
None Unchecked Activity nan None 10.1021/acs.jnatprod.1c00689
None Unchecked Activity nan None 10.1021/acsmedchemlett.2c00196
None Unchecked EC50 100000.0 nM 10.1021/acsmedchemlett.2c00196
None Unchecked IC50 5300.0 nM 10.1021/acsmedchemlett.2c00196
None Unchecked Potency 0.005258 nM None
None Unchecked Potency 661.9 nM None
None Unchecked Potency 1662.6 nM None
None Unchecked Potency 33173.4 nM None
None Unchecked Potency 104903.6 nM None

Metabolism Information