ID: ALA3144392

Max Phase: Preclinical

Molecular Formula: C15H15N2O10P

Molecular Weight: 414.26

Molecule Type: Small molecule

Representations

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

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

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: 0

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