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Compound Detail

CHEMBL886

5-FLUORODEOXYURIDYLATE
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O=c1[nH]c(=O)n([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)cc1F
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL886
Name 5-FLUORODEOXYURIDYLATE
Phase Preclinical
Structure Type MOL
InChI Key HFEKDTCAMMOLQP-RRKCRQDMSA-N

Known Names

5-Fluoro-2-Deoxyuridine Monophosphate (Fdump)
8
Targets
24
Activities
3
Assay Types
1
PK Parameters
20
Publications
1
Known Names

Molecular Properties

326.2
MW (Da)
-1.57
ALogP
7
HBA
4
HBD
151.1
PSA (Ų)
0.48
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C9H12FN2O8P
MW 326.17
Aromatic Rings 1
Heavy Atoms 21
NP-Likeness 0.72

Activity Summary

IC50 12 meas. best 8.85
Ki 10 meas. best 8.0
Kd 2 meas. best 8.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
L5178Y
CHEMBL614720
 IC50 8.85 8.85 1.4 1
CCRF-CEM
CHEMBL382
 IC50 8.26 6.546 5.5 5
Thymidylate synthase
CHEMBL3160
 IC50 8.1 7.75 8.0 3
Thymidylate synthase
CHEMBL3160
 Ki 8.0 7.73 10.0 4
Thymidylate synthase
CHEMBL5328
 Kd 8.0 8.0 10.0 1
Thymidylate synthase
CHEMBL6137
 Ki 8.0 8.0 10.0 1
Thymidylate synthase
CHEMBL1952
 Ki 7.85 7.85 14.0 1
Thymidylate synthase
CHEMBL5328
 Ki 7.85 6.8433 14.0 3
L1210
CHEMBL386
 IC50 7.82 7.82 15.0 1
L929
CHEMBL612267
 IC50 5.17 5.17 6800.0 1

Pharmacokinetic Data

Parameter Value Units Species
T1/2 0.8833 hr -

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
L5178Y IC50 = 1.4 nM 8.85 Comparative inhibition of L5178Y cell growth in vitro (concentration required fo... 6779007
CCRF-CEM IC50 = 5.5 nM 8.26 In vitro cytotoxicity of compounds were determined on Inhibition of human leukem... 8917645
Thymidylate synthase IC50 = 8.0 nM 8.1 Inhibition of cellular thymidylate synthase activity of mouse fibroblast (L929 T... 8917645
Thymidylate synthase Ki = 10.0 nM 8.0 Apparent Ki value was measured by competitive inhibition of Thymidylate Synthase... 8246229
Thymidylate synthase Ki = 10.0 nM 8.0 Compound was evaluated for the inhibition of dTMP synthetase with respect to dUM... 7328576
Thymidylate synthase Kd = 10.0 nM 8.0 Binding affinity to amethopterin-resistant Lactobacillus casei thymidylate synth... 410930
Thymidylate synthase Ki = 14.0 nM 7.85 Inhibition of amethopterin-resistant Lactobacillus casei thymidylate synthetase-... 410930
Thymidylate synthase Ki = 14.0 nM 7.85 Competitive inhibition of thymidylate synthase purified from methotrexate-resist... 114660
Thymidylate synthase Ki = 14.0 nM 7.85 Inhibition of human thymidylate synthase expressed in Escherichia coli incubated... 23075414
L1210 IC50 = 15.0 nM 7.82 In vitro cytotoxicity of compounds were determined on murine leukemia cell line ... 8917645
Thymidylate synthase IC50 = 17.0 nM 7.77 Inhibition of cellular thymidylate synthase activity of murine leukemia cell lin... 8917645
Thymidylate synthase Ki = 20.0 nM 7.7 Time-independent inhibition of thymidylate synthase from parenteral L1210 cells 11101356
Thymidylate synthase Ki = 20.0 nM 7.7 Apparent Ki value was measured by competitive inhibition of Thymidylate Synthase... 8246229
Thymidylate synthase Ki = 30.0 nM 7.52 Time-independent inhibition of thymidylate synthase from FdUrd-resistant L1210 c... 11101356
Thymidylate synthase IC50 = 42.0 nM 7.38 Inhibition of cellular thymidylate synthase activity of murine leukemia cell lin... 8917645
CCRF-CEM IC50 = 50.0 nM 7.3 Cytostatic activity against human CEM cells expressing human ENT1 transporter af... 21892829
CCRF-CEM IC50 = 1060.0 nM 5.97 Cytostatic activity against human CEM cells expressing human ENT1 transporter af... 21892829
CCRF-CEM IC50 = 1740.0 nM 5.76 Cytostatic activity against human CEM cells expressing human ENT1 transporter af... 21892829
CCRF-CEM IC50 = 3600.0 nM 5.44 Cytostatic activity against ENT1 transporter-deficient human CEM cells after 72 ... 21892829
L929 IC50 = 6800.0 nM 5.17 In vitro cytotoxicity of compounds were determined on mouse fibroblast (L929 TK-... 8917645

Literature References

PubMed DOI Target Context # Activities
11101356 10.1021/jm000975u Thymidylate synthase 10
8246229 10.1021/jm00075a016 Thymidylate synthase 10
21892829 10.1021/jm200815w CCRF-CEM 7
8917645 10.1021/jm9603680 Thymidylate synthase 4
6708047 10.1021/jm00370a005 L1210 4
410930 10.1021/jm00221a021 Thymidylate synthase 4
6708047 10.1021/jm00370a005 Unchecked 3
3027328 10.1021/jm00157a022 Human alphaherpesvirus 2 3
6228661 10.1021/jm00367a003 ADMET 3
3007759 10.1021/jm00154a011 Human alphaherpesvirus 1 3
3007759 10.1021/jm00154a011 Human alphaherpesvirus 2 3
3027328 10.1021/jm00157a022 Human alphaherpesvirus 1 3
6779007 10.1021/jm00185a016 L5178Y 2
12941330 10.1016/s0960-894x(03)00643-7 Thymidylate kinase 2
12217356 10.1016/s0960-894x(02)00551-6 Thymidylate kinase 2
3027328 10.1021/jm00157a022 L1210 2
3007759 10.1021/jm00154a011 Raji 2
3007759 10.1021/jm00154a011 L1210 2
8917645 10.1021/jm9603680 Unchecked 2
11101356 10.1021/jm000975u Unchecked 2

Data from ChEMBL 36 via Core Engine