But-3-ynyl diphosphate

ID: ALA2251810

PubChem CID: 46236598

Max Phase: Preclinical

Molecular Formula: C4H8O7P2

Molecular Weight: 230.05

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C#CCCOP(=O)(O)OP(=O)(O)O

Standard InChI:  InChI=1S/C4H8O7P2/c1-2-3-4-10-13(8,9)11-12(5,6)7/h1H,3-4H2,(H,8,9)(H2,5,6,7)

Standard InChI Key:  GYFWQGOZWDTPGX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 13 12  0  0  0  0  0  0  0  0999 V2000
   11.0065   -2.2891    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   11.0379   -1.4725    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2835   -2.6702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5921   -2.2346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8699   -2.6106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6979   -2.7247    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4208   -2.3436    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   13.1123   -2.7792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4523   -1.5271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4147   -3.1573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9991   -3.1037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1797   -2.1717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4902   -1.7332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  1  3  1  0
  3  4  1  0
  4  5  1  0
  1  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  7 10  1  0
  1 11  1  0
  5 12  1  0
 12 13  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA2251810

   BUT-3-YNYL 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: 230.05

Molecular Weight (Monoisotopic): 229.9745

AlogP: 0.24

#Rotatable Bonds: 5

Polar Surface Area: 113.29

Molecular Species: ACID

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.78

CX Basic pKa: ┄

CX LogP: -0.55

CX LogD: -5.58

Aromatic Rings: ┄

Heavy Atoms: 13

QED Weighted: 0.35

Np Likeness Score: 0.97

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