Phosphoric acid mono-[5-(5-ethyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl] ester

ID: ALA606019

Chembl Id: CHEMBL606019

PubChem CID: 46875010

Max Phase: Preclinical

Molecular Formula: C11H17N2O9P

Molecular Weight: 352.24

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCc1cn(C2O[C@H](COP(=O)(O)O)[C@@H](O)[C@@H]2O)c(=O)[nH]c1=O

Standard InChI:  InChI=1S/C11H17N2O9P/c1-2-5-3-13(11(17)12-9(5)16)10-8(15)7(14)6(22-10)4-21-23(18,19)20/h3,6-8,10,14-15H,2,4H2,1H3,(H,12,16,17)(H2,18,19,20)/t6-,7-,8+,10?/m1/s1

Standard InChI Key:  SIHFJGHFGIXZKJ-UUBZBTQISA-N

Alternative Forms

1. Parent:

   

   ALA606019

   P-e5Ura-Araf

Molecule Features

Natural Product: No

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: 352.24

Molecular Weight (Monoisotopic): 352.0672

AlogP: -2.17

#Rotatable Bonds: 5

Polar Surface Area: 171.31

Molecular Species: ACID

HBA: 8

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 1.23

CX Basic pKa: ┄

CX LogP: -1.70

CX LogD: -5.23

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.37

Np Likeness Score: 1.00

References

1. 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]

2. 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]

Source

Source(1):

• Scientific Literature