Phosphoric acid mono-{5-[5-(4-benzyloxy-phenyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-3-hydroxy-tetrahydro-furan-2-ylmethyl} ester

ID: ALA3144190

PubChem CID: 90663791

Max Phase: Preclinical

Molecular Formula: C22H23N2O9P

Molecular Weight: 490.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=c1[nH]c(=O)n([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)cc1-c1ccc(OCc2ccccc2)cc1

Standard InChI:  InChI=1S/C22H23N2O9P/c25-18-10-20(33-19(18)13-32-34(28,29)30)24-11-17(21(26)23-22(24)27)15-6-8-16(9-7-15)31-12-14-4-2-1-3-5-14/h1-9,11,18-20,25H,10,12-13H2,(H,23,26,27)(H2,28,29,30)/t18-,19+,20+/m0/s1

Standard InChI Key:  WBQVPNGHCJTSSK-XUVXKRRUSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA3144190

   [(2R,3S,5R)-5-[2,4-dioxo-5-(4-phenylmethoxyphenyl)pyrimidin-1-yl]-3-hydroxyoxolan-2-yl]methyl dihydrogen phosphate

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: 490.41

Molecular Weight (Monoisotopic): 490.1141

AlogP: 1.54

#Rotatable Bonds: 8

Polar Surface Area: 160.31

Molecular Species: ACID

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 1.23

CX Basic pKa: ┄

CX LogP: 1.60

CX LogD: -1.93

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.34

Np Likeness Score: 0.38

References

1. Chang G, Schwepler D, Decedue CJ, Balzarini J, De Clercq E, Mertes MP..  (1988)  Linear free energy relationship studies of enzyme active site binding: thymidylate synthase.,  31  (6): [PMID:3373483] [10.1021/jm00401a013]

Source

Source(1):

• Scientific Literature