(-)-Lichesterinic acid

ID: ALA3903682

PubChem CID: 9927283

Max Phase: Preclinical

Molecular Formula: C19H32O4

Molecular Weight: 324.46

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C19H32O4/c1-3-4-5-6-7-8-9-10-11-12-13-14-16-17(18(20)21)15(2)19(22)23-16/h16H,3-14H2,1-2H3,(H,20,21)/t16-/m0/s1

Standard InChI Key:  SLQVVNFTCYVCPB-INIZCTEOSA-N

Molfile:  

     RDKit          2D

 23 23  0  0  0  0  0  0  0  0999 V2000
   26.6784   -5.2911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.4956   -5.2911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7499   -4.5144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0870   -4.0323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4282   -4.5144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9751   -5.9528    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.6509   -4.2623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4807   -3.4630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7033   -3.2108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5331   -2.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1401   -1.8645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9174   -2.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5245   -1.5696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3018   -1.8218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9088   -1.2747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6861   -1.5268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2932   -0.9798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0705   -1.2319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6775   -0.6849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0857   -3.2151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5275   -4.2630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7928   -2.8054    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.3774   -2.8076    0.0000 O   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
M  END

Alternative Forms

1. Parent:

   

   ALA3903682

   Lichesterinic acid

Molecule Features

Natural Product: Yes

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: 324.46

Molecular Weight (Monoisotopic): 324.2301

AlogP: 5.01

#Rotatable Bonds: 13

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: 6.20

CX LogD: 2.79

Aromatic Rings: ┄

Heavy Atoms: 23

QED Weighted: 0.38

Np Likeness Score: 1.11

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