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name Structure Reference Source Properties Activities Metabolism

dUMP(2-)

AlkaPlorer ID: AK014087

Synonym: '', "2'-Deoxyuridine 5'-phosphate", 'dUMP dianion', "2'-deoxyuridine 5'-monophosphate", "deoxyuridine 5'-phosphate dianion", 'deoxyuridylate', 'dUMP', 'Deoxyuridylic acid', "Deoxyuridine 5'-phosphate", "deoxyuridine 5'-phosphate(2-)", 'Deoxyuridine monophosphate', '964-26-1'

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

Structure

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

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InChI: InChI=1S/C9H13N2O8P/c12-5-3-8(11-2-1-7(13)10-9(11)14)19-6(5)4-18-20(15,16)17/h1-2,5-6,8,12H,3-4H2,(H,10,13,14)(H2,15,16,17)/t5-,6+,8+/m0/s1

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InChIKey: JSRLJPSBLDHEIO-SHYZEUOFSA-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: 308.183

TPSA？: 151.08

MolLogP？: -1.7056999999999998

Number of H-Donors: 4

Number of H-Acceptors: 7

RingCount: 2

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Bos taurus Thymidylate synthase Ki 8000.0 nM 10.1021/jm00215a010
Escherichia coli Thymidylate synthase Km 2000.0 nM 10.1021/jm00142a008
Homo sapiens Thymidylate kinase Kcat 4.8 /s 10.1021/jm1011462
Homo sapiens Thymidylate kinase Kcat/Km 28000.0 /M/s 10.1021/jm1011462
Homo sapiens Thymidylate kinase Km 170000.0 nM 10.1021/jm1011462
Homo sapiens Thymidylate synthase k2 760000.0 M-1 s-1 10.1021/jm00159a025
Homo sapiens Thymidylate synthase Ki 3000.0 nM 10.1021/jm00378a031
Homo sapiens Thymidylate synthase Ki nan nM 10.1021/jm00376a004
Homo sapiens Thymidylate synthase Km 5250.0 nM 10.1016/j.bmcl.2008.03.016
Lacticaseibacillus casei Lacticaseibacillus casei Ki 2300.0 nM 10.1021/jm00362a012
Lactobacillus casei Thymidylate synthase Ki 2260.0 nM 10.1021/jm00221a021
Lactobacillus casei Thymidylate synthase Km 5000.0 nM 10.1021/jm00144a003
Lactobacillus casei Thymidylate synthase Km 5200.0 nM 10.1021/jm00221a021
Mus musculus Thymidylate synthase Ki 6500.0 nM 10.1021/jm00215a010
Mycobacterium tuberculosis Thymidylate kinase Km 2100000.0 nM 10.1016/s0960-894x(02)00551-6
Mycobacterium tuberculosis Thymidylate kinase Km 2100000.0 nM 10.1016/s0960-894x(03)00643-7
Mycobacterium tuberculosis Thymidylate kinase Vm 3.5 uM min-1mg-1 10.1016/s0960-894x(03)00643-7
Mycobacterium tuberculosis Thymidylate kinase Vm 3.5 uM min-1 (mg of protein)-1 10.1016/s0960-894x(02)00551-6
Trypanosoma cruzi (strain CL Brener) Deoxyuridine triphosphatase Ki 18400.0 nM 10.1016/j.bmcl.2006.04.027
None NON-PROTEIN TARGET IC50 8000.0 nM 10.1021/jm960175c
None Unchecked IC50 nan nM 10.1021/jm960175c
None Unchecked Ki 7600.0 nM 10.1021/jm00215a010

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
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
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
AKRT021040 Nc1ccn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)c(=O)n1>>O=c1ccn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)c(=O)[nH]1 DCMP-DEAMINASE-RXN
AKRT021056 Nc1ccn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)O2)c(=O)n1>>O=c1ccn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)c(=O)[nH]1 3.5.4.30-RXN
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
AKRT021146 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>>O=c1[nH]c(=O)n([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)cc1CO 48424
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
AKRT022059 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](COP(=O)(O)O)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)OP(=O)(O)O)O2)c(=O)[nH]1 None
AKRT023287 O=C(O)c1cc(=O)[nH]c(=O)n1[C@H]1C[C@H](O)[C@@H](COP(=O)(O)O)O1>>O=C=O.O=c1ccn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)c(=O)[nH]1 None
AKRT023288 O=C(O)c1cc(=O)[nH]c(=O)n1[C@H]1C[C@H](O)[C@@H](COP(=O)(O)O)O1>>O=c1ccn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)c(=O)[nH]1 enzymemap_81609
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
AKRT024779 O=c1ccn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)NP(=O)(O)OP(=O)(O)O)O2)c(=O)[nH]1>>O=c1ccn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)c(=O)[nH]1 enzymemap_80260
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
AKRT024781 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](COP(=O)(O)OP(=O)(O)O)O2)c(=O)[nH]1 R02098
AKRT024783 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](COP(=O)(O)O)O2)c(=O)[nH]1 RXN-14220
AKRT024789 O=c1ccn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)O2)c(=O)[nH]1>>O=c1ccn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)c(=O)[nH]1 DUTP-PYROP-RXN
AKRT024793 O=c1ccn([C@H]2C[C@H](OP(=O)(O)O)[C@@H](COP(=O)(O)O)O2)c(=O)[nH]1>>O=c1ccn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)c(=O)[nH]1 enzymemap_56896