Navigation

name Structure Reference Source Properties Activities Metabolism

Deoxyuridine

AlkaPlorer ID: AK002875

Synonym: None

IUPAC Name: 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione

Structure

SMILES: O=C1C=CN([C@H]2C[C@H](O)[C@@H](CO)O2)C(=O)N1

copy

InChI: InChI=1S/C9H12N2O5/c12-4-6-5(13)3-8(16-6)11-2-1-7(14)10-9(11)15/h1-2,5-6,8,12-13H,3-4H2,(H,10,14,15)/t5-,6+,8+/m0/s1

copy

InChIKey: MXHRCPNRJAMMIM-SHYZEUOFSA-N

copy

Source

Species Genus Family Order Class Phylum Kingdom Domain
Mus musculus Mus Muridae Rodentia Mammalia Chordata Metazoa Eukaryota

Properties Information

Molecule Weight: 228.204

TPSA？: 104.55

MolLogP？: -1.8226999999999995

Number of H-Donors: 3

Number of H-Acceptors: 6

RingCount: 2

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Chlorocebus sabaeus Vero IC50 2.2 nM 10.1021/jm981132u
Cricetulus griseus Thymidine kinase, cytosolic Inhibition 38.0 % 10.1021/jm00192a005
Cricetulus griseus Thymidine kinase, cytosolic Inhibition 59.0 % 10.1021/jm00192a005
Cryptosporidium hominis Bifunctional dihydrofolate reductase-thymidylate synthase Inhibition -5.3 % 10.1016/j.bmcl.2019.03.022
Enterococcus faecium Enterococcus faecium ED50 37.0 uM 10.1021/jm00209a010
Escherichia coli K-12 Thymidine phosphorylase Activity 83.0 % 10.1016/j.bmc.2008.01.038
Escherichia coli K-12 Thymidine phosphorylase Activity 88.0 % 10.1016/j.bmc.2008.01.038
Hepatitis B virus Hepatitis B virus Inhibition 0.0 % 10.1016/j.bmcl.2010.08.120
Hepatitis B virus Hepatitis B virus Inhibition nan % 10.1016/j.bmcl.2010.08.120
Homo sapiens A2780 Activity nan None 10.1021/np049849+
Homo sapiens DNA polymerase beta Activity nan None 10.1021/np049849+
Homo sapiens Dual specificity phosphatase Cdc25B Activity nan None 10.1021/np049849+
Homo sapiens HeLa IC50 nan nM 10.1016/j.bmcl.2004.10.039
Homo sapiens Thymidine kinase, cytosolic Activity nan None 10.1021/jm00100a029
Homo sapiens Thymidine kinase, cytosolic ID50 400.0 uM 10.1021/jm00100a029
Homo sapiens Thymidine kinase, cytosolic Relative phosphorylation 1.0 None 10.1021/jm990125i
Homo sapiens Thymidine phosphorylase Km 559000.0 nM 10.1021/jm00182a029
Mus musculus Deoxycytidine kinase Activity 88.0 % 10.1021/jm00366a006
Mus musculus Deoxycytidine kinase Activity 92.0 % 10.1021/jm00366a006
Mus musculus Monoamine oxidase A Activity nan None 10.1021/jm800656v
Mus musculus Monoamine oxidase B Activity nan None 10.1021/jm800656v
Mus musculus Mus musculus Ki 0.11 None 10.1021/jm00387a015
Mus musculus Mus musculus Ki 110000.0 nM 10.1021/jm00005a010
Mus musculus Mus musculus Ki 125000.0 nM 10.1021/jm9408326
Mus musculus Mus musculus Ki 130000.0 nM 10.1021/jm00126a024
Mus musculus Thymidine kinase, cytosolic Activity 65.0 % 10.1021/jm00366a006
Mus musculus Thymidine kinase, cytosolic Activity 93.0 % 10.1021/jm00366a006
Mus musculus Thymidine kinase, cytosolic Relative phosphorylation 0.55 None 10.1021/jm990125i
Rattus norvegicus Thymidine kinase Inhibition 90.0 % 10.1021/jm00348a007
Rattus norvegicus Thymidine kinase 2 Inhibition 74.0 % 10.1021/jm00348a007
None ADMET CC50 200.0 ug.mL-1 10.1016/j.bmcl.2010.08.120
None No relevant target pKa 9.3 None 10.1021/jm00209a010
None Unchecked Ki 9500.0 nM 10.1021/jm00209a010
None Unchecked Ki 125000.0 nM 10.1021/jm00164a039
None Unchecked Ki 290000.0 nM 10.1021/jm00198a017
None Unchecked Vmax 0.88 uM min-1 10.1021/jm00182a029

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT010340 CCc1c[nH]c(=O)[nH]c1=O.O=c1ccn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]1>>CCc1cn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]c1=O enzymemap_39204
AKRT010341 CCc1c[nH]c(=O)[nH]c1=O.O=c1ccn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]1>>CCc1cn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]c1=O.O=c1cc[nH]c(=O)[nH]1 None
AKRT014851 Cc1c[nH]c(=O)[nH]c1=O.O=c1ccn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]1>>Cc1cn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]c1=O enzymemap_38612
AKRT015112 Cc1cn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]c1=O>>O=c1ccn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]1 enzymemap_39129
AKRT021030 Nc1ccn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)n1>>O=c1ccn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]1 CYTIDEAM-RXN
AKRT022058 Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]1O.O=c1ccn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]1>>Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]1O.O=c1ccn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)c(=O)[nH]1 None
AKRT023856 O=P(O)(O)O[C@@H]1C[C@H](O)[C@@H](CO)O1.O=c1cc[nH]c(=O)[nH]1>>O=c1ccn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]1 R02484
AKRT023875 O=P(O)(O)O[C@H]1O[C@H](CO)[C@@H](O)[C@H]1O.O=c1cc[nH]c(=O)[nH]1>>O=c1ccn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]1 MNXR136586
AKRT024361 O=c1cc[nH]c(=O)[nH]1.O=P(O)(O)O[C@@H]1C[C@H](O)[C@@H](CO)O1>>O=c1ccn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]1 enzymemap_38968
AKRT024402 O=c1ccn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)[nH]1>>O=c1ccn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]1 enzymemap_10808
AKRT024771 O=c1ccn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]1.O=c1[nH]cc(/C=C/Br)c(=O)[nH]1>>O=c1[nH]c(=O)n([C@H]2C[C@H](O)[C@@H](CO)O2)cc1/C=C\Br enzymemap_38608
AKRT024772 O=c1ccn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]1.O=c1[nH]cc(C(F)(F)F)c(=O)[nH]1>>O=c1[nH]c(=O)n([C@H]2C[C@H](O)[C@@H](CO)O2)cc1C(F)(F)F enzymemap_38611
AKRT024773 O=c1ccn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]1>>O=C1C[C@H](O)[C@@H](CO)O1 1.14.11.10-RXN
AKRT024774 O=c1ccn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]1>>O=P(O)(O)O[C@@H]1C[C@H](O)[C@@H](CO)O1 URA-PHOSPH-RXN
AKRT024775 O=c1ccn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]1>>O=P(O)(O)O[C@@H]1C[C@H](O)[C@@H](CO)O1.O=c1cc[nH]c(=O)[nH]1 None
AKRT024776 O=c1ccn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]1>>O=c1cc[nH]c(=O)[nH]1 URA-PHOSPH-RXN
AKRT024777 O=c1ccn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]1>>O=c1ccn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)[nH]1 1.14.11.3-RXN
AKRT024778 O=c1ccn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]1>>O=c1ccn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)c(=O)[nH]1 DURIDKI-RXN
AKRT024780 O=c1ccn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)c(=O)[nH]1>>O=c1ccn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]1 R02102
AKRT024782 O=c1ccn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)OP(=O)(O)O)O2)c(=O)[nH]1>>O=c1ccn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]1 enzymemap_80251
AKRT024791 O=c1ccn([C@H]2C[C@H](O)[C@@H](COP(O)(=S)OP(=O)(O)OP(=O)(O)O)O2)c(=O)[nH]1>>O=c1ccn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]1 enzymemap_80249
AKRT024792 O=c1ccn([C@H]2C[C@H](OP(=O)(O)O)[C@@H](CO)O2)c(=O)[nH]1>>O=c1ccn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]1 RXN-14523