acetic acid (S)-2-acetoxy-3,4-dioxo-pentyl ester

ID: ALA393458

PubChem CID: 44440597

Max Phase: Preclinical

Molecular Formula: C9H12O6

Molecular Weight: 216.19

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)OC[C@H](OC(C)=O)C(=O)C(C)=O

Standard InChI:  InChI=1S/C9H12O6/c1-5(10)9(13)8(15-7(3)12)4-14-6(2)11/h8H,4H2,1-3H3/t8-/m0/s1

Standard InChI Key:  RJTZPRQEDHJPHV-QMMMGPOBSA-N

Molfile:  

     RDKit          2D

 15 14  0  0  1  0  0  0  0  0999 V2000
   -2.3500   -0.3083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6355    0.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9211   -0.3083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2066    0.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5079   -0.3083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2066    0.9292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9211   -1.1333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0645    0.1042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6355    0.9292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7789   -0.3083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4934    0.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7789   -1.1333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3500    1.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3500    2.1667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0645    0.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  8  1  0
  2  9  1  6
  4  5  1  0
  8 10  1  0
  2  3  1  0
 10 11  1  0
  4  6  2  0
 10 12  2  0
  1  2  1  0
  9 13  1  0
  3  7  2  0
 13 14  2  0
  3  4  1  0
 13 15  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA393458

   [(2S)-2-acetyloxy-3,4-dioxopentyl] acetate

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: 216.19

Molecular Weight (Monoisotopic): 216.0634

AlogP: -0.36

#Rotatable Bonds: 5

Polar Surface Area: 86.74

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: -0.02

CX LogD: -0.02

Aromatic Rings: ┄

Heavy Atoms: 15

QED Weighted: 0.46

Np Likeness Score: 0.86

References

1. Frezza M, Soulère L, Balestrino D, Gohar M, Deshayes C, Queneau Y, Forestier C, Doutheau A..  (2007)  Ac2-DPD, the bis-(O)-acetylated derivative of 4,5-dihydroxy-2,3-pentanedione (DPD) is a convenient stable precursor of bacterial quorum sensing autoinducer AI-2.,  17  (5): [PMID:17169556] [10.1016/j.bmcl.2006.11.076]

Source

Source(1):

• Scientific Literature