[2-[(2,4-dioxopyrimidin-1-yl)methoxy]ethoxy-sulfanyl-phosphinothioyl]dihydrogen phosphate

ID: ALA4558341

PubChem CID: 155557503

Max Phase: Preclinical

Molecular Formula: C7H12N2O8P2S2

Molecular Weight: 378.26

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=c1ccn(COCCOP(=S)(S)OP(=O)(O)O)c(=O)[nH]1

Standard InChI:  InChI=1S/C7H12N2O8P2S2/c10-6-1-2-9(7(11)8-6)5-15-3-4-16-19(20,21)17-18(12,13)14/h1-2H,3-5H2,(H,20,21)(H,8,10,11)(H2,12,13,14)

Standard InChI Key:  PXYXDJZONXJPJO-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 21 21  0  0  0  0  0  0  0  0999 V2000
   13.2430   -8.6644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9469   -7.4361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2944  -10.7129    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4066  -11.8283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0023  -11.1200    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    9.7110  -10.7132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2417   -9.4847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5936  -11.8257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9525   -9.8976    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.1234  -10.7136    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6689   -9.4842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9523  -10.7143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6661   -8.6577    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.3762   -9.8907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5399  -10.7139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4149  -11.1200    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   11.8336  -11.1221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0063  -11.8257    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   13.2460  -11.1225    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8192  -11.8283    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   13.9506   -8.2528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  9 11  1  0
 21  2  2  0
  9 12  1  0
 19 15  1  0
  7  9  1  0
  6  5  1  0
 17 10  1  0
 21  1  1  0
 16  6  1  0
  5  3  1  0
 18 16  2  0
 16 20  1  0
 10 16  1  0
 11 14  2  0
 13 21  1  0
 12 19  1  0
  8  5  1  0
 15 17  1  0
  7  1  2  0
  5  4  2  0
 11 13  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4558341

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 378.26

Molecular Weight (Monoisotopic): 377.9510

AlogP: -0.21

#Rotatable Bonds: 8

Polar Surface Area: 140.08

Molecular Species: ACID

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.26

CX Basic pKa: ┄

CX LogP: -0.17

CX LogD: -4.27

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.27

Np Likeness Score: 0.03

References

1. Nassir M, Pelletier J, Arad U, Arguin G, Khazanov N, Gendron FP, Sévigny J, Senderowitz H, Fischer B..  (2019)  Structure-activity relationship study of NPP1 inhibitors based on uracil-N1-(methoxy)ethyl-β-phosphate scaffold.,  184  [PMID:31610377] [10.1016/j.ejmech.2019.111754]

2. Nadel, Yael Y and 11 more authors.  2014-06-12  Highly potent and selective ectonucleotide pyrophosphatase/phosphodiesterase I inhibitors based on an adenosine 5'-(α or γ)-thio-(α,β- or β,γ)-methylenetriphosphate scaffold.  [PMID:24846781]

3. Lee, Sang-Yong SY and 5 more authors.  2016-07-15  Thiazolo[3,2-a]benzimidazol-3(2H)-one derivatives: Structure-activity relationships of selective nucleotide pyrophosphatase/phosphodiesterase1 (NPP1) inhibitors.  [PMID:27265686]

4. Zelikman, Vadim V and 8 more authors.  2018-05-10  Highly Selective and Potent Ectonucleotide Pyrophosphatase-1 (NPP1) Inhibitors Based on Uridine 5'-Pα,α-Dithiophosphate Analogues.  [PMID:29681152]

5. Nassir, Molhm and 8 more authors.  2019-12-15  Structure-activity relationship study of NPP1 inhibitors based on uracil-N1-(methoxy)ethyl-β-phosphate scaffold.  [PMID:31610377]

6. Ahmad, Haseen and 7 more authors.  2020-12-15  Synthesis of biphenyl oxazole derivatives via Suzuki coupling and biological evaluations as nucleotide pyrophosphatase/phosphodiesterase-1 and -3 inhibitors.  [PMID:32883636]

Source

Source(1):

• Scientific Literature