(S)-4-Methyl-5-oxo-2-pentadecyl-2,5-dihydrofuran-3-carboxylic acid

ID: ALA3894744

PubChem CID: 132578553

Max Phase: Preclinical

Molecular Formula: C21H36O4

Molecular Weight: 352.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCCCCCCCC[C@@H]1OC(=O)C(C)=C1C(=O)O

Standard InChI:  InChI=1S/C21H36O4/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-18-19(20(22)23)17(2)21(24)25-18/h18H,3-16H2,1-2H3,(H,22,23)/t18-/m0/s1

Standard InChI Key:  SYVOXIHVISVSED-SFHVURJKSA-N

Molfile:  

     RDKit          2D

 25 25  0  0  0  0  0  0  0  0999 V2000
   28.4077  -21.5277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.2249  -21.5277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4792  -20.7509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8163  -20.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1575  -20.7509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7044  -22.1893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.3802  -20.4988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2100  -19.6995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4327  -19.4473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2624  -18.6481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8694  -18.1010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6467  -18.3532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2538  -17.8061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0311  -18.0583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6381  -17.5112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4155  -17.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0225  -17.2163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7998  -17.4685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4069  -16.9214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8150  -19.4516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2568  -20.4995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5221  -19.0420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.1067  -19.0441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.1842  -17.1736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7912  -16.6265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  1  1  0
  2  6  2  0
  5  7  1  1
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
  4 20  1  0
  3 21  1  0
 20 22  1  0
 20 23  2  0
 19 24  1  0
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3894744

   ---

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: 352.52

Molecular Weight (Monoisotopic): 352.2614

AlogP: 5.79

#Rotatable Bonds: 15

Polar Surface Area: 63.60

Molecular Species: ACID

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.38

CX Basic pKa: ┄

CX LogP: 7.09

CX LogD: 3.68

Aromatic Rings: ┄

Heavy Atoms: 25

QED Weighted: 0.30

Np Likeness Score: 1.02

References

1. Sweidan A, Chollet-Krugler M, van de Weghe P, Chokr A, Tomasi S, Bonnaure-Mallet M, Bousarghin L..  (2016)  Design, synthesis and biological evaluation of potential antibacterial butyrolactones.,  24  (22): [PMID:27687969] [10.1016/j.bmc.2016.09.040]

Source

Source(1):

• Scientific Literature