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Inosine

AlkaPlorer ID: AK005802

Synonym: None

IUPAC Name: 9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-purin-6-one

Structure

SMILES: O=C1N=CNC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O

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InChI: InChI=1S/C10H12N4O5/c15-1-4-6(16)7(17)10(19-4)14-3-13-5-8(14)11-2-12-9(5)18/h2-4,6-7,10,15-17H,1H2,(H,11,12,18)/t4-,6-,7-,10-/m1/s1

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InChIKey: UGQMRVRMYYASKQ-KQYNXXCUSA-N

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Properties Information

Molecule Weight: 268.229

TPSA？: 133.49

MolLogP？: -2.2689

Number of H-Donors: 4

Number of H-Acceptors: 8

RingCount: 3

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Bos taurus Adenosine deaminase Ki 500000.0 nM 10.1021/jm00389a015
Cavia porcellus Ileum Activity 0.0 % 10.1021/np50060a041
Cavia porcellus Ileum Inhibition 23.0 % 10.1021/np50060a041
Chlorocebus sabaeus Vero IC50 0.23 nM 10.1021/jm981132u
Equus caballus Ferritin light chain Potency 891.3 nM None
Homo sapiens Adenosylhomocysteinase k cat 44.2 M-1 10.1016/s0960-894x(03)00331-7
Homo sapiens Adenosylhomocysteinase Ki 925000.0 nM 10.1016/s0960-894x(03)00331-7
Homo sapiens Adenosylhomocysteinase Km 2500.0 nM 10.1016/s0960-894x(03)00331-7
Homo sapiens Ataxin-2 Potency 794.3 nM None
Homo sapiens Bromodomain adjacent to zinc finger domain protein 2B Potency 707.9 nM None
Homo sapiens DU-145 IC50 250000.0 nM 10.1039/C3MD00159H
Homo sapiens Geminin Potency 5804.8 nM None
Homo sapiens HaCaT IC50 250000.0 nM 10.1039/C3MD00159H
Homo sapiens Homo sapiens T1/2 7.5 hr 10.1021/jm100012m
Homo sapiens Isocitrate dehydrogenase [NADP] cytoplasmic Potency 20596.2 nM None
Homo sapiens MCF7 IC50 250000.0 nM 10.1039/C3MD00159H
Homo sapiens Mothers against decapentaplegic homolog 3 Potency 112.2 nM None
Homo sapiens Muscleblind-like protein 1 Potency 158.5 nM None
Homo sapiens Nuclear factor erythroid 2-related factor 2 Potency 29092.9 nM None
Homo sapiens Purine nucleoside phosphorylase Activity 100.0 % 10.1021/jm00207a008
Homo sapiens Purine nucleoside phosphorylase Drug metabolism 391000.0 nmol/mg/hr 10.1016/j.ejmech.2015.12.029
Homo sapiens Purine nucleoside phosphorylase Kcat 56.0 /s 10.1021/acs.jmedchem.9b00182
Homo sapiens Purine nucleoside phosphorylase Km 40000.0 nM 10.1016/j.bmcl.2008.08.047
Homo sapiens Purine nucleoside phosphorylase Km 750000.0 nM 10.1016/j.bmcl.2008.08.047
Homo sapiens Solute carrier family 22 member 1 Activity nan None 10.1124/mol.51.6.913
Homo sapiens Solute carrier organic anion transporter family member 1B1 Inhibition 110.7 % 10.1124/mol.112.084152
Homo sapiens Solute carrier organic anion transporter family member 1B3 Inhibition 107.34 % 10.1124/mol.112.084152
Homo sapiens Survival motor neuron protein Potency 1258.9 nM None
Mus musculus J774.A1 Activity nan None 10.1128/aac.01029-10
Perknaster fuscus Perknaster fuscus Activity nan None 10.1021/np970358h
Plasmodium falciparum Plasmodium falciparum Potency 414.7 nM None
Plasmodium falciparum Purine nucleoside phosphorylase Kcat 0.34 /s 10.1021/acs.jmedchem.9b00182
Rattus norvegicus C6 IC50 250000.0 nM 10.1039/C3MD00159H
Rattus norvegicus L6 IC50 250000.0 nM 10.1039/C3MD00159H
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
Spinacia oleracea Spinacia oleracea I50 nan None 10.1021/jf070082b
Sulfolobus solfataricus (strain ATCC 35092 / DSM 1617 / JCM 11322 /P2) Purine nucleoside phosphorylase Drug metabolism 84000.0 nmol/mg/hr 10.1016/j.ejmech.2015.12.029
Trichomonas vaginalis Trichomonas vaginalis GI 19.2 % 10.1016/j.bmcl.2012.03.087
None ADMET Drug metabolism 2000.0 nmol/mg/hr 10.1016/j.ejmech.2015.12.029
None ADMET Drug metabolism 154000.0 nmol/mg/hr 10.1016/j.ejmech.2015.12.029
None ADMET Drug metabolism 342000.0 nmol/mg/hr 10.1016/j.ejmech.2015.12.029
None Erythroleukemia cell line Differentiation 12.0 % 10.1021/jm00148a018
None Erythroleukemia cell line ID50 7.0 mM 10.1021/jm00148a018
None Erythroleukemia cell line Optimal concentration 7.0 mM 10.1021/jm00148a018
None Hepatotoxicity Hepatotoxicity nan None 10.1021/tx900326k
None No relevant target T1/2 5.0 hr 10.1016/j.ejmech.2014.05.073
None Unchecked Ac50 3.548 uM None
None Unchecked Ac50 17.78 uM None
None Unchecked AC50 3548.1 nM None
None Unchecked AC50 17782.8 nM None
None Unchecked IC50 900000.0 nM 10.1021/np50030a005
None Unchecked IC50 nan None 10.1021/acs.jmedchem.7b01066
None Unchecked Ki 380000.0 nM 10.1039/C8MD00372F
None Unchecked Km 434000.0 nM 10.1016/j.ejmech.2012.07.052

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT019391 N[C@@H](CCS)C(=O)O.O=c1[nH]cnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O>>N[C@@H](CCSC[C@H]1O[C@@H](n2cnc3c(=O)[nH]cnc32)[C@H](O)[C@@H]1O)C(=O)O enzymemap_58396
AKRT019413 N[C@@H](CCSC[C@H]1O[C@@H](n2cnc3c(=O)[nH]cnc32)[C@H](O)[C@@H]1O)C(=O)O>>N[C@@H](CCS)C(=O)O.O=c1[nH]cnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O None
AKRT019414 N[C@@H](CCSC[C@H]1O[C@@H](n2cnc3c(=O)[nH]cnc32)[C@H](O)[C@@H]1O)C(=O)O>>O=c1[nH]cnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O enzymemap_58395
AKRT019416 N[C@@H](CCSC[C@H]1O[C@@H](n2cnc3c(=O)nc[nH]c32)[C@H](O)[C@@H]1O)C(=O)O>>O=c1[nH]cnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O RXN-20698
AKRT020854 Nc1ccn([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O)c(=O)n1.OC[C@H]1O[C@@H](n2cnc3c(O)ncnc32)[C@H](O)[C@@H]1O>>Nc1ccn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)n1 69592
AKRT020855 Nc1ccn([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O)c(=O)n1.OC[C@H]1O[C@@H](n2cnc3c(O)ncnc32)[C@H](O)[C@@H]1O>>O=c1[nH]cnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]1O 69592
AKRT021115 Nc1nc2[nH]cnc2c(=O)[nH]1.O=c1[nH]cnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O>>Nc1nc2c(ncn2[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)[nH]1 RXN-22626
AKRT021116 Nc1nc2[nH]cnc2c(=O)[nH]1.O=c1[nH]cnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O>>O=c1[nH]cnc2nc[nH]c12 RXN-22626
AKRT021275 Nc1nc2c(ncn2[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)[nH]1.O=c1[nH]cnc2nc[nH]c12>>O=c1[nH]cnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O RXN-22626
AKRT021311 Nc1nc2c(ncn2[C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O)c(=O)[nH]1.OC[C@H]1O[C@@H](n2cnc3c(O)ncnc32)[C@H](O)[C@@H]1O>>Nc1nc2c(ncn2[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)[nH]1 69584
AKRT021312 Nc1nc2c(ncn2[C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O)c(=O)[nH]1.OC[C@H]1O[C@@H](n2cnc3c(O)ncnc32)[C@H](O)[C@@H]1O>>O=c1[nH]cnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]1O 69584
AKRT021619 Nc1ncnc2[nH]cnc12.O=c1[nH]cnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O>>Nc1ncnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O RXN-22628
AKRT021620 Nc1ncnc2[nH]cnc12.O=c1[nH]cnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O>>O=c1[nH]cnc2nc[nH]c12 RXN-22628
AKRT021623 Nc1ncnc2[nH]cnc12.OC[C@H]1O[C@@H](n2cnc3c(O)ncnc32)[C@H](O)[C@@H]1O>>Nc1ncnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O MNXR131902
AKRT021624 Nc1ncnc2[nH]cnc12.OC[C@H]1O[C@@H](n2cnc3c(O)ncnc32)[C@H](O)[C@@H]1O>>O=c1[nH]cnc2nc[nH]c12 MNXR131902
AKRT021674 Nc1ncnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O.O=c1[nH]cnc2nc[nH]c12>>O=c1[nH]cnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O RXN-22628
AKRT021687 Nc1ncnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O>>O=c1[nH]cnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O ADENODEAMIN-RXN
AKRT022047 Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]1O.O=c1[nH]cnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O>>Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]1O.O=c1[nH]cnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]1O None
AKRT022239 Nc1ncnc2c1ncn2[C@H]1C[C@H](O)[C@@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)O1.O=c1[nH]cnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O>>Nc1ncnc2c1ncn2[C@H]1C[C@H](O)[C@@H](COP(=O)(O)OP(=O)(O)O)O1.O=c1[nH]cnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]1O None
AKRT023872 O=P(O)(O)O[C@H]1O[C@H](CO)[C@@H](O)[C@H]1O.O=c1[nH]cnc2[nH]cnc12>>O=c1[nH]cnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O R01863
AKRT024123 O=c1[nH]c(=O)c2nc[nH]c2[nH]1.O=c1[nH]cnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O>>O=c1[nH]c(=O)c2ncn([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)c2[nH]1 RXN-22629
AKRT024127 O=c1[nH]c(=O)c2ncn([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)c2[nH]1.O=c1[nH]cnc2nc[nH]c12>>O=c1[nH]cnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O RXN-22629
AKRT024170 O=c1[nH]cnc2[nH]cnc12.O=P(O)(O)O[C@H]1O[C@H](CO)[C@@H](O)[C@H]1O>>O=c1[nH]cnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O enzymemap_38448
AKRT024172 O=c1[nH]cnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O.O=c1ccn([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]2O)c(=O)[nH]1>>O=c1[nH]cnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]1O.O=c1ccn([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]2O)c(=O)[nH]1 None
AKRT024173 O=c1[nH]cnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O>>O=C(O)[C@H]1O[C@@H](n2cnc3c(=O)[nH]cnc32)[C@H](O)[C@@H]1O NUCLEOSIDE-OXIDASE-RXN
AKRT024174 O=c1[nH]cnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O>>O=C[C@H]1O[C@@H](n2cnc3c(=O)[nH]cnc32)[C@H](O)[C@@H]1O RXN-7802
AKRT024175 O=c1[nH]cnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O>>O=P(O)(O)O[C@H]1O[C@H](CO)[C@@H](O)[C@H]1O INOPHOSPHOR-RXN
AKRT024176 O=c1[nH]cnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O>>O=c1[nH]cnc2[nH]cnc12 R01770
AKRT024177 O=c1[nH]cnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O>>O=c1[nH]cnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]1O INOSINEKIN-RXN
AKRT024178 O=c1[nH]cnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O>>O=c1[nH]cnc2nc[nH]c12 INOSINE-NUCLEOSIDASE-RXN
AKRT024179 O=c1[nH]cnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O>>OC[C@H]1OC(O)[C@H](O)[C@@H]1O INOSINE-NUCLEOSIDASE-RXN
AKRT024180 O=c1[nH]cnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](OP(=O)(O)O)[C@H]1O>>O=c1[nH]cnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O enzymemap_56667
AKRT024186 O=c1[nH]cnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]1O>>O=c1[nH]cnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O RXN-7607
AKRT024415 O=c1ccn([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O)c(=O)[nH]1.OC[C@H]1O[C@@H](n2cnc3c(O)ncnc32)[C@H](O)[C@@H]1O>>O=c1[nH]cnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]1O 69588
AKRT024416 O=c1ccn([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O)c(=O)[nH]1.OC[C@H]1O[C@@H](n2cnc3c(O)ncnc32)[C@H](O)[C@@H]1O>>O=c1ccn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)[nH]1 69588
AKRT024836 OC[C@H]1O[C@@H](n2cnc3c(O)ncnc32)[C@H](O)[C@@H]1O>>Nc1ncnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O 69596
AKRT024837 OC[C@H]1O[C@@H](n2cnc3c(O)ncnc32)[C@H](O)[C@@H]1O>>O=C[C@H](O)[C@H](O)[C@H](O)CO MNXR175520
AKRT024838 OC[C@H]1O[C@@H](n2cnc3c(O)ncnc32)[C@H](O)[C@@H]1O>>O=c1[nH]cnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]1O 69572
AKRT024839 OC[C@H]1O[C@@H](n2cnc3c(O)ncnc32)[C@H](O)[C@@H]1O>>O=c1[nH]cnc2nc[nH]c12 MNXR173242
AKRT024840 OC[C@H]1O[C@@H](n2cnc3c(O)ncnc32)[C@H](O)[C@@H]1O>>OC[C@H]1O[C@@H](O)[C@H](O)[C@@H]1O MNXR173242
AKRT024841 OC[C@H]1O[C@@H](n2cnc3c(O)ncnc32)[C@H](O)[C@@H]1O>>O[C@@H]1CO[C@@H](O)[C@H](O)[C@@H]1O MNXR179365