(S)-2-Hexadecyl-4-methyl-5-oxo-2,5-dihydrofuran-3-carboxylic acid

ID: ALA3953019

PubChem CID: 132578554

Max Phase: Preclinical

Molecular Formula: C22H38O4

Molecular Weight: 366.54

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C22H38O4/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-19-20(21(23)24)18(2)22(25)26-19/h19H,3-17H2,1-2H3,(H,23,24)/t19-/m0/s1

Standard InChI Key:  ZOZVMQGVRDVZLD-IBGZPJMESA-N

Molfile:  

     RDKit          2D

 26 26  0  0  0  0  0  0  0  0999 V2000
   35.3703   -6.1042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.1875   -6.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4419   -5.3275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7789   -4.8454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1202   -5.3275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6671   -6.7659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.3429   -5.0753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1726   -4.2761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3953   -4.0239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2250   -3.2246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8321   -2.6775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6094   -2.9297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2164   -2.3826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9937   -2.6348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6008   -2.0877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3781   -2.3399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9851   -1.7928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.7624   -2.0450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.3695   -1.4979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7777   -4.0282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2194   -5.0760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4848   -3.6185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.0693   -3.6207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.1468   -1.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.7538   -1.2030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.5312   -1.4552    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
 25 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3953019

   ---

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: 366.54

Molecular Weight (Monoisotopic): 366.2770

AlogP: 6.18

#Rotatable Bonds: 16

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: 7.53

CX LogD: 4.12

Aromatic Rings: ┄

Heavy Atoms: 26

QED Weighted: 0.26

Np Likeness Score: 0.98

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