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

ID: ALA1230421

Cas Number: 3590-47-4

PubChem CID: 12803287

Max Phase: Preclinical

Molecular Formula: C10H15N2O9P

Molecular Weight: 338.21

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cn([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O)c(=O)[nH]c1=O

Standard InChI:  InChI=1S/C10H15N2O9P/c1-4-2-12(10(16)11-8(4)15)9-7(14)6(13)5(21-9)3-20-22(17,18)19/h2,5-7,9,13-14H,3H2,1H3,(H,11,15,16)(H2,17,18,19)/t5-,6-,7-,9-/m1/s1

Standard InChI Key:  IGWHDMPTQKSDTL-JXOAFFINSA-N

Molfile:  

     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
   -0.5068    4.6289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5068    3.8039    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3318    3.8039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3182    3.8039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5068    2.9789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2076    2.5664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2076    1.7414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8751    1.2565    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4598    1.2565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2444    1.5115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2049    0.4719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6898   -0.1955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6201    0.4719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1051   -0.1955    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7695   -0.9492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0510   -1.0355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2544   -1.6167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0749   -1.5304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5598   -2.1979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4105   -0.7767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2310   -0.6905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9255   -0.1093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  2  0
  4  2  1  0
  5  2  1  0
  6  5  1  0
  7  6  1  1
  7  8  1  0
  9  7  1  0
 13  8  1  0
  9 10  1  6
 11  9  1  0
 11 12  1  6
 13 11  1  0
 13 14  1  1
 15 14  1  0
 22 14  1  0
 15 16  2  0
 15 17  1  0
 18 17  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 20 22  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1230421

   5-Methyluridine 5'-monophosphate

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: 338.21

Molecular Weight (Monoisotopic): 338.0515

AlogP: -2.43

#Rotatable Bonds: 4

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: -2.14

CX LogD: -5.67

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.37

Np Likeness Score: 1.23

References

1. Gangjee A, Yu J, McGuire JJ, Cody V, Galitsky N, Kisliuk RL, Queener SF..  (2000)  Design, synthesis, and X-ray crystal structure of a potent dual inhibitor of thymidylate synthase and dihydrofolate reductase as an antitumor agent.,  43  (21): [PMID:11052789] [10.1021/jm000200l]

Source

Source(1):

• Scientific Literature