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name Structure Reference Source Properties Activities Metabolism

Thymidine Monophosphate

AlkaPlorer ID: AK013588

Synonym: None

IUPAC Name: [(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl dihydrogen phosphate

Structure

SMILES: CC1=CN([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)C(=O)NC1=O

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InChI: InChI=1S/C10H15N2O8P/c1-5-3-12(10(15)11-9(5)14)8-2-6(13)7(20-8)4-19-21(16,17)18/h3,6-8,13H,2,4H2,1H3,(H,11,14,15)(H2,16,17,18)/t6-,7+,8+/m0/s1

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InChIKey: GYOZYWVXFNDGLU-XLPZGREQSA-N

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Source

Species Genus Family Order Class Phylum Kingdom Domain
Escherichia coli Escherichia Enterobacteriaceae Enterobacterales Gammaproteobacteria Pseudomonadota None Bacteria

Properties Information

Molecule Weight: 322.21000000000004

TPSA？: 151.07999999999998

MolLogP？: -1.3972800000000003

Number of H-Donors: 4

Number of H-Acceptors: 7

RingCount: 2

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Bacillus subtilis Bacillus subtilis MIC 0.5 ug.mL-1 10.1021/acs.jnatprod.0c00719
Bacillus thuringiensis Bacillus thuringiensis MIC 0.5 ug.mL-1 10.1021/acs.jnatprod.0c00719
Homo sapiens Thymidine kinase, cytosolic Km 5000.0 nM 10.1021/jm021108n
Homo sapiens Thymidylate kinase Activity 5600.0 % 10.1128/aac.01432-06
Homo sapiens Thymidylate kinase Kcat 1.8 /s 10.1128/aac.01432-06
Homo sapiens Thymidylate kinase Kcat 3.0 /s 10.1021/jm1011462
Homo sapiens Thymidylate kinase Kcat/Km 150000.0 /M/s 10.1021/jm1011462
Homo sapiens Thymidylate kinase Km 5000.0 nM 10.1021/jm040847w
Homo sapiens Thymidylate kinase Km 8300.0 nM 10.1128/aac.01432-06
Homo sapiens Thymidylate kinase Km 20000.0 nM 10.1021/jm1011462
Homo sapiens Thymidylate synthase Ki nan nM 10.1021/jm00376a004
Lactobacillus casei Thymidylate synthase Ki 8690.0 nM 10.1021/jm00221a021
Lactobacillus casei Thymidylate synthase Ki 15500.0 nM 10.1021/jm00221a021
Micrococcus luteus Micrococcus luteus MIC 0.5 ug.mL-1 10.1021/acs.jnatprod.0c00719
Mus musculus LM Incorporation rate 256.0 c.p.m. hr-1 10.1021/jm00155a033
Mus musculus LM Incorporation rate 295.0 c.p.m. hr-1 10.1021/jm00155a033
Mus musculus LM Incorporation rate 323.0 c.p.m. hr-1 10.1021/jm00155a033
Mus musculus LM Incorporation rate 381.0 c.p.m. hr-1 10.1021/jm00155a033
Mus musculus LM Incorporation rate 596.0 c.p.m. hr-1 10.1021/jm00155a033
Mus musculus LM Incorporation rate 668.0 c.p.m. hr-1 10.1021/jm00155a033
Mus musculus LM Incorporation rate 837.0 c.p.m. hr-1 10.1021/jm00155a033
Mycobacterium tuberculosis Thymidylate kinase Ki 4500.0 nM 10.1016/j.ejmech.2010.09.056
Mycobacterium tuberculosis Thymidylate kinase Km 4500.0 nM 10.1016/s0960-894x(02)00551-6
Mycobacterium tuberculosis Thymidylate kinase Km 4500.0 nM 10.1016/s0960-894x(03)00643-7
Mycobacterium tuberculosis Thymidylate kinase Km 4500.0 nM 10.1021/jm021108n
Mycobacterium tuberculosis Thymidylate kinase Km 4500.0 nM 10.1021/jm040847w
Mycobacterium tuberculosis Thymidylate kinase Km 4500.0 nM 10.1021/jm0492296
Mycobacterium tuberculosis Thymidylate kinase Km 4500.0 nM 10.1021/jm0706158
Mycobacterium tuberculosis Thymidylate kinase Km 40000.0 nM 10.1016/s0960-894x(03)00643-7
Mycobacterium tuberculosis Thymidylate kinase Vm 10.6 uM min-1mg-1 10.1016/s0960-894x(03)00643-7
Mycobacterium tuberculosis Thymidylate kinase Vm 10.6 uM min-1 (mg of protein)-1 10.1016/s0960-894x(02)00551-6
Staphylococcus aureus Staphylococcus aureus MIC 2.0 ug.mL-1 10.1021/acs.jnatprod.0c00719
None ADMET pKa2 6.5 None 10.1021/jm00166a019
None NON-PROTEIN TARGET IC50 10000.0 nM 10.1021/jm960175c
None Unchecked IC50 11000.0 nM 10.1021/jm960175c
None Unchecked Ki 17000.0 nM 10.1016/j.ejmech.2015.01.035
None Unchecked Km 5000.0 nM 10.1021/jm0706158
None Unchecked Selectivity index 1.1 None 10.1021/jm040847w
None Unchecked SI 1.1 None 10.1021/jm021108n

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT000092 *C(=O)CC[C@H](NC(=O)c1ccc(N2C[C@H]3CNc4nc(N)[nH]c(=O)c4N3C2)cc1)C(=O)O.O=c1ccn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)c(=O)[nH]1>>Cc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)c(=O)[nH]c1=O THYMIDYLATESYN-RXN
AKRT001968 C=O.O=c1ccn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)c(=O)[nH]1>>Cc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)c(=O)[nH]c1=O 68268
AKRT015083 Cc1cn([C@@]2(c3ccc([N+](=O)[O-])cc3)C[C@H](O)[C@@H](COP(=O)(O)O)O2)c(=O)[nH]c1=O>>Cc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)c(=O)[nH]c1=O enzymemap_54460
AKRT015084 Cc1cn([C@@]2(c3ccc([N+](=O)[O-])cc3)C[C@H](O)[C@@H](COP(=O)(O)O)O2)c(=O)[nH]c1=O>>Cc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)c(=O)[nH]c1=O.O=[N+]([O-])c1ccc(O)cc1 None
AKRT015098 Cc1cn([C@H]2C[C@H](O)[C@@H](C(OP(=O)(O)O)c3ccc([N+](=O)[O-])cc3)O2)c(=O)[nH]c1=O>>Cc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)c(=O)[nH]c1=O enzymemap_57212
AKRT015108 Cc1cn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]c1=O>>Cc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)c(=O)[nH]c1=O THYKI-RXN
AKRT015114 Cc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)c(=O)[nH]c1=O.N=c1[nH]c2c(c(=O)[nH]1)N=C(CNc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)CN2>>N=c1[nH]c2c(c(=O)[nH]1)N1CN(c3ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc3)CC1CN2 enzymemap_27430
AKRT015115 Cc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)c(=O)[nH]c1=O.N=c1[nH]c2c(c(=O)[nH]1)N=C(CNc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)CN2>>N=c1[nH]c2c(c(=O)[nH]1)N1CN(c3ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc3)C[C@H]1CN2 enzymemap_27449
AKRT015116 Cc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)c(=O)[nH]c1=O.Nc1nc2c(c(=O)[nH]1)N=C(CNc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)CN2>>Nc1nc2c(c(=O)[nH]1)N1CN(c3ccc(C(=O)NC(CCC(=O)O)C(=O)O)cc3)C[C@H]1CN2 R02101
AKRT015117 Cc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)c(=O)[nH]c1=O.Nc1nc2c(c(=O)[nH]1)N=C(CNc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)CN2>>Nc1nc2c(c(=O)[nH]1)N1CN(c3ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc3)CC1CN2 enzymemap_27430
AKRT015118 Cc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)c(=O)[nH]c1=O.Nc1nc2c(c(=O)[nH]1)N=C(CNc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)CN2>>Nc1nc2c(c(=O)[nH]1)N1CN(c3ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc3)C[C@H]1CN2 enzymemap_27449
AKRT015119 Cc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)c(=O)[nH]c1=O.Nc1nc2c(c(=O)[nH]1)N[C@@H](CNc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)CN2>>Nc1nc2c(c(=O)[nH]1)N1CN(c3ccc(C(=O)NC(CCC(=O)O)C(=O)O)cc3)C[C@H]1CN2 R06613
AKRT015120 Cc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)c(=O)[nH]c1=O.Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]1O>>Cc1cn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]c1=O.Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]1O None
AKRT015121 Cc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)c(=O)[nH]c1=O.Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]1O>>Cc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)OP(=O)(O)O)O2)c(=O)[nH]c1=O.Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]1O None
AKRT015122 Cc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)c(=O)[nH]c1=O.Nc1ncnc2c1ncn2[C@H]1C[C@H](O)[C@@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)O1>>Cc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)OP(=O)(O)O)O2)c(=O)[nH]c1=O.Nc1ncnc2c1ncn2[C@H]1C[C@H](O)[C@@H](COP(=O)(O)OP(=O)(O)O)O1 None
AKRT015123 Cc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)c(=O)[nH]c1=O.O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)COP(=O)(O)O>>Cc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)OP(=O)(O)O)O2)c(=O)[nH]c1=O.O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO None
AKRT015124 Cc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)c(=O)[nH]c1=O.O=P(O)(O)OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O>>Cc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)OP(=O)(O)O)O2)c(=O)[nH]c1=O.OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O None
AKRT015125 Cc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)c(=O)[nH]c1=O>>Cc1c[nH]c(=O)[nH]c1=O R12956
AKRT015126 Cc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)c(=O)[nH]c1=O>>Cc1cn([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O)c(=O)[nH]c1=O enzymemap_10807
AKRT015127 Cc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)c(=O)[nH]c1=O>>Cc1cn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]c1=O R01569
AKRT015128 Cc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)c(=O)[nH]c1=O>>Cc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)OP(=O)(O)O)O2)c(=O)[nH]c1=O DTMPKI-RXN
AKRT015129 Cc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)c(=O)[nH]c1=O>>O=P(O)(O)OC[C@H]1OC(O)C[C@@H]1O 52712
AKRT015130 Cc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)c(=O)[nH]c1=O>>O=P(O)(O)O[C@@H]1C[C@H](O)[C@@H](CO)O1 R12956
AKRT015131 Cc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)c(=O)[nH]c1=O>>O=c1ccn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)c(=O)[nH]1 R02101
AKRT015135 Cc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)OC[C@H]3O[C@@H](n4cc(C)c(=O)[nH]c4=O)C[C@@H]3O)O2)c(=O)[nH]c1=O>>Cc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)c(=O)[nH]c1=O enzymemap_57180
AKRT015143 Cc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)OP(=O)(O)O)O2)c(=O)[nH]c1=O>>Cc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)c(=O)[nH]c1=O R02092
AKRT015147 Cc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)OP(=O)(O)OC[C@H]3O[C@@H](n4cc(C)c(=O)[nH]c4=O)C[C@@H]3O)O2)c(=O)[nH]c1=O>>Cc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)c(=O)[nH]c1=O enzymemap_80742
AKRT015162 Cc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)O2)c(=O)[nH]c1=O>>Cc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)c(=O)[nH]c1=O R11323
AKRT015227 Cc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)OP(=O)(O)O[C@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)O2)c(=O)[nH]c1=O>>Cc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)c(=O)[nH]c1=O enzymemap_80704
AKRT015228 Cc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)OP(=O)(O)O[C@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)O2)c(=O)[nH]c1=O>>Cc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)c(=O)[nH]c1=O.O=P(O)(O)O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O None
AKRT015235 Cc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)Oc3ccc([N+](=O)[O-])cc3)O2)c(=O)[nH]c1=O>>Cc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)c(=O)[nH]c1=O enzymemap_54448
AKRT015236 Cc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)Oc3ccc([N+](=O)[O-])cc3)O2)c(=O)[nH]c1=O>>Cc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)c(=O)[nH]c1=O.O=[N+]([O-])c1ccc(O)cc1 None
AKRT015239 Cc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)Oc3ccc4c(C)cc(=O)oc4c3)O2)c(=O)[nH]c1=O>>Cc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)c(=O)[nH]c1=O enzymemap_57179
AKRT015244 Cc1cn([C@H]2C[C@H](OP(=O)(O)O)[C@@H](COP(=O)(O)O)O2)c(=O)[nH]c1=O>>Cc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)c(=O)[nH]c1=O enzymemap_56895
AKRT016695 N=c1[nH]c2c(c(=O)[nH]1)N1CN(c3ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc3)CC1CN2.O=c1ccn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)c(=O)[nH]1>>Cc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)c(=O)[nH]c1=O enzymemap_27427
AKRT016698 N=c1[nH]c2c(c(=O)[nH]1)N1CN(c3ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc3)C[C@H]1CN2.O=c1ccn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)c(=O)[nH]1>>Cc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)c(=O)[nH]c1=O enzymemap_27424
AKRT021133 Nc1nc2c(c(=O)[nH]1)N1CN(c3ccc(C(=O)NC(CCC(=O)O)C(=O)O)cc3)C[C@H]1CN2.O=c1ccn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)c(=O)[nH]1>>Cc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)c(=O)[nH]c1=O R02101
AKRT021139 Nc1nc2c(c(=O)[nH]1)N1CN(c3ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc3)CC1CN2.O=c1ccn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)c(=O)[nH]1>>Cc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)c(=O)[nH]c1=O enzymemap_27427
AKRT021145 Nc1nc2c(c(=O)[nH]1)N1CN(c3ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc3)C[C@H]1CN2.O=c1ccn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)c(=O)[nH]1>>Cc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)c(=O)[nH]c1=O MNXR191200
AKRT021151 Nc1nc2c(c(=O)[nH]1)N1CN(c3ccc(C(=O)N[C@H](CCC(=O)O)C(=O)O)cc3)CC1CN2.O=c1ccn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)c(=O)[nH]1>>Cc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)c(=O)[nH]c1=O enzymemap_27443