Pyridin-3-yl-ethyl-diphosphate

ID: ALA2251821

PubChem CID: 46236745

Max Phase: Preclinical

Molecular Formula: C7H11NO7P2

Molecular Weight: 283.11

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=P(O)(O)OP(=O)(O)OCCc1cccnc1

Standard InChI:  InChI=1S/C7H11NO7P2/c9-16(10,11)15-17(12,13)14-5-3-7-2-1-4-8-6-7/h1-2,4,6H,3,5H2,(H,12,13)(H2,9,10,11)

Standard InChI Key:  SMIWJXJRPPYIHA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 17 17  0  0  0  0  0  0  0  0999 V2000
    9.4334  -22.7080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4323  -23.5275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1403  -23.9365    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8500  -23.5270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8472  -22.7044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1385  -22.2991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5533  -22.2931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2626  -22.6990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9687  -22.2878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6780  -22.6937    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   14.3841  -22.2824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0934  -22.6884    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   15.7995  -22.2771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6811  -23.5109    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0965  -23.5056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0891  -21.8702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6735  -21.8743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 10 14  2  0
 12 15  2  0
 12 16  1  0
 10 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2251821

   PYRIDIN-3-YL-ETHYL-DIPHOSPHATE

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: 283.11

Molecular Weight (Monoisotopic): 283.0011

AlogP: 0.85

#Rotatable Bonds: 6

Polar Surface Area: 126.18

Molecular Species: ACID

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.78

CX Basic pKa: 4.93

CX LogP: -1.65

CX LogD: -5.30

Aromatic Rings: 1

Heavy Atoms: 17

QED Weighted: 0.66

Np Likeness Score: 0.45

References

1. Wang K, Wang W, No JH, Zhang Y, Zhang Y, Oldfield E..  (2010)  Inhibition of the Fe(4)S(4)-cluster-containing protein IspH (LytB): electron paramagnetic resonance, metallacycles, and mechanisms.,  132  (19): [PMID:20426416] [10.1021/ja909664j]

2. Hale I, O'Neill PM, Berry NG, Odom A, Sharma R.  (2012)  The MEP pathway and the development of inhibitors as potential anti-infective agents,  3  (4): [10.1039/C2MD00298A]

3. Masini T, Hirsch AK..  (2014)  Development of inhibitors of the 2C-methyl-D-erythritol 4-phosphate (MEP) pathway enzymes as potential anti-infective agents.,  57  (23): [PMID:25210872] [10.1021/jm5010978]

Source

Source(1):

• Scientific Literature