[5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-hydroxytetrahydrofuran-2-yl]methyl dihydrogen phosphate (dUMP)

ID: ALA211312

Chembl Id: CHEMBL211312

Cas Number: 964-26-1

PubChem CID: 65063

Max Phase: Preclinical

Molecular Formula: C9H13N2O8P

Molecular Weight: 308.18

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 2'-Deoxyuridinemonophosphate | dUMP|Deoxyuridine monophosphate|2'-Deoxyuridine 5'-monophosphate|2'-deoxyuridylic acid|Deoxyuridylic acid|2'-deoxy-5'-uridylic acid|Deoxyuridine 5'-phosphate|Deoxy-UMP|2'-Deoxyuridylate|2'-Deoxyuridine 5'-phosphate|964-26-1|Deoxyuridine 5'-monophosphate|deoxyuridylate|5'-Uridylic acid, 2'-deoxy-|2'-DEOXYURIDINE-5'-MONOPHOSPHATE|Uridine, 2'-deoxy-, 5'-(dihydrogen phosphate)|Uridine, 2'-deoxy-, 5'-phosphate|CHEMBL211312|N9J10KFG94|CHEBI:17622|EINECS 213-518-9|BRN 004Show More⌵

Canonical SMILES:  O=c1ccn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)c(=O)[nH]1

Standard 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

Standard InChI Key:  JSRLJPSBLDHEIO-SHYZEUOFSA-N

Alternative Forms

1. Parent:

   

   ALA211312

   DEOXYURIDINE MONOPHOSPHATE

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 308.18

Molecular Weight (Monoisotopic): 308.0410

AlogP: -1.71

#Rotatable Bonds: 4

Polar Surface Area: 151.08

Molecular Species: ACID

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.23

CX Basic pKa: ┄

CX LogP: -1.64

CX LogD: -5.16

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.48

Np Likeness Score: 1.16

References

1. Coderre JA, Santi DV, Matsuda A, Watanabe KA, Fox JJ..  (1983)  Mechanism of action of 2',5-difluoro-1-arabinosyluracil.,  26  (8): [PMID:6876083] [10.1021/jm00362a012]

2. Nakayama C, Wataya Y, Santi DV, Saneyoshi M, Ueda T..  (1981)  Interaction of 1-(5-phospho-beta-D-arabinofuranosyl)-5-substituted-uracils with thymidylate synthetase: mechanism-based inhibition by 1-(5-phospho-beta-D-arabinosyl)-5-fluorouracil.,  24  (10): [PMID:7328576] [10.1021/jm00142a008]

3. Goldstein S, Pogolotti AL, Garvey EP, Santi DV..  (1984)  Interaction of N4-hydroxy-2'-deoxycytidylic acid with thymidylate synthetase.,  27  (10): [PMID:6434741] [10.1021/jm00376a004]

4. Barr PJ, Nolan PA, Santi DV, Robins MJ..  (1981)  Inhibition of thymidylate synthetase by 5-alkynyl-2'-deoxyuridylates.,  24  (12): [PMID:6796687] [10.1021/jm00144a003]

5. Srinivasan A, Amarnath V, Broom AD, Zou FC, Cheng YC..  (1984)  A potent multisubstrate analogue inhibitor of human thymidylate synthetase.,  27  (12): [PMID:6502602] [10.1021/jm00378a031]

6. Vadnere MK, Maggiora L, Mertes MP..  (1986)  Thiol addition to quinones: model reactions for the inactivation of thymidylate synthase by 5-p-benzoquinonyl-2'-deoxyuridine 5'-phosphate.,  29  (9): [PMID:3746818] [10.1021/jm00159a025]

7. Vanheusden V, Munier-Lehmann H, Pochet S, Herdewijn P, Van Calenbergh S..  (2002)  Synthesis and evaluation of thymidine-5'-O-monophosphate analogues as inhibitors of Mycobacterium tuberculosis thymidylate kinase.,  12  (19): [PMID:12217356] [10.1016/s0960-894x(02)00551-6]

8. Traynor AJ, Hall ET, Walker G, Miller WH, Melançon P, Kuchta RD..  (1996)  Inhibition of UDP-N-acetylglucosamine import into Golgi membranes by nucleoside monophosphates.,  39  (15): [PMID:8709123] [10.1021/jm960175c]

9. Vanheusden V, Van Rompaey P, Munier-Lehmann H, Pochet S, Herdewijn P, Van Calenbergh S..  (2003)  Thymidine and thymidine-5'-O-monophosphate analogues as inhibitors of Mycobacterium tuberculosis thymidylate kinase.,  13  (18): [PMID:12941330] [10.1016/s0960-894x(03)00643-7]

10. Mc Carthy OK, Schipani A, Buendía AM, Ruiz-Perez LM, Kaiser M, Brun R, Pacanowska DG, Gilbert IH..  (2006)  Design, synthesis and evaluation of novel uracil amino acid conjugates for the inhibition of Trypanosoma cruzi dUTPase.,  16  (14): [PMID:16677813] [10.1016/j.bmcl.2006.04.027]

11. Jarmuła A, Dowierciał A, Rode W..  (2008)  A molecular modeling study of the interaction of 2'-fluoro-substituted analogues of dUMP/FdUMP with thymidylate synthase.,  18  (8): [PMID:18362071] [10.1016/j.bmcl.2008.03.016]

12. Topalis D, Pradère U, Roy V, Caillat C, Azzouzi A, Broggi J, Snoeck R, Andrei G, Lin J, Eriksson S, Alexandre JA, El-Amri C, Deville-Bonne D, Meyer P, Balzarini J, Agrofoglio LA..  (2011)  Novel antiviral C5-substituted pyrimidine acyclic nucleoside phosphonates selected as human thymidylate kinase substrates.,  54  (1): [PMID:21128666] [10.1021/jm1011462]

13. Edelman MS, Barfknecht RL, Huet-Rose R, Boguslawski S, Mertes MP..  (1977)  Thymidylate synthetase inhibitors. Synthesis of N-substituted 5-aminomethyl-2'-deoxyuridine 5'-phosphates.,  20  (5): [PMID:323484] [10.1021/jm00215a010]

14. Wataya Y, Santi DV, Hansch C..  (1977)  Inhibition of Lactobacillus casei thymidylate synthetase by 5-substituted 2'-deoxyuridylates. Preliminary quantitative structure-activity relationship.,  20  (11): [PMID:410930] [10.1021/jm00221a021]

Source

Source(1):

• Scientific Literature