Phosphoric acid mono-{5-[5-(3,6-dioxo-cyclohexa-1,4-dienyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-3-hydroxy-tetrahydro-furan-2-ylmethyl} ester

ID: ALA3144392

Max Phase: Preclinical

Molecular Formula: C15H15N2O10P

Molecular Weight: 414.26

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1C=CC(=O)C(c2cn([C@H]3C[C@H](O)[C@@H](COP(=O)(O)O)O3)c(=O)[nH]c2=O)=C1

Standard InChI:  InChI=1S/C15H15N2O10P/c18-7-1-2-10(19)8(3-7)9-5-17(15(22)16-14(9)21)13-4-11(20)12(27-13)6-26-28(23,24)25/h1-3,5,11-13,20H,4,6H2,(H,16,21,22)(H2,23,24,25)/t11-,12+,13+/m0/s1

Standard InChI Key:  DNVOIKAHGQQSAD-YNEHKIRRSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
    7.0496   -4.5874    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3551   -5.1686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7141   -5.3411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1990   -6.0085    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5647   -3.9200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0195   -5.9223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8701   -4.5012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1755   -5.0824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8197   -3.1353    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8667   -0.5879    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    5.7397   -3.9200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1522   -2.6504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6605   -5.7498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5111   -4.3287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4848   -3.1353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3316   -4.2425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1522   -1.8254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4809   -5.6636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8165   -4.9099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8936   -5.4273    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8667   -1.4129    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5044   -6.5897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8667    0.2371    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0262   -3.6612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9659   -6.3310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6917   -0.5879    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0417   -0.5879    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7002   -2.8804    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  7  2  0
  3  1  1  0
  4  3  1  0
  5  1  1  1
  6  2  1  0
  7  1  1  0
  8  2  1  0
  9  5  1  0
 10 21  1  0
 11  5  1  0
 12  9  1  0
 13  8  2  0
 14  8  1  0
 15 11  1  0
 16 14  1  0
 12 17  1  1
 18 13  1  0
 19 16  2  0
 20  3  2  0
 21 17  1  0
 22  6  2  0
 23 10  2  0
 24 14  2  0
 25 18  2  0
 26 10  1  0
 27 10  1  0
 15 28  1  6
  4  6  1  0
 15 12  1  0
 18 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3144392

   ---

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: 414.26

Molecular Weight (Monoisotopic): 414.0464

AlogP: -1.61

#Rotatable Bonds: 5

Polar Surface Area: 185.22

Molecular Species: ACID

HBA: 9

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 12

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 1.23

CX Basic pKa: ┄

CX LogP: -1.18

CX LogD: -4.70

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.32

Np Likeness Score: 1.31

References

1. 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]

2. Al-Razzak LA, Schwepler D, Decedue CJ, Balzarini J, De Clercq E, Mertes MP..  (1987)  5-Quinone derivatives of 2'-deoxyuridine 5'-phosphate: inhibition and inactivation of thymidylate synthase, antitumor cell, and antiviral studies.,  30  (2): [PMID:3027341] [10.1021/jm00385a026]

Source

Source(1):

• Scientific Literature