(+)-lichesterinic acid

ID: ALA3318191

Cas Number: 70579-62-3

PubChem CID: 21116528

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-/m1/s1

Standard InChI Key:  SLQVVNFTCYVCPB-MRXNPFEDSA-N

Molfile:  

     RDKit          2D

 23 23  0  0  0  0  0  0  0  0999 V2000
   19.1247  -23.7123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9497  -23.7123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.2066  -22.9282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5372  -22.4415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8723  -22.9282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9916  -22.6743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.5360  -21.6165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6391  -24.3791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9736  -25.1333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4878  -25.8001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8224  -26.5541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3366  -27.2209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6712  -27.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1854  -28.6418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5199  -29.3960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0341  -30.0628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3688  -30.8168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8830  -31.4836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2176  -32.2377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7318  -32.9046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0839  -22.6737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9121  -21.8668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4711  -23.2260    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  1  0
  4  5  2  0
  5  1  1  0
  3  6  2  0
  4  7  1  0
  1  8  1  6
  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
 19 20  1  0
 21 22  1  0
 21 23  2  0
  5 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3318191

   (R)-2-Tridecyl-2,5-dihydro-4-methyl-5-oxo-3-furoic 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. Le Lamer AC, Authier H, Rouaud I, Coste A, Boustie J, Pipy B, Gouault N..  (2014)  Protolichesterinic acid derivatives: α-methylene-γ-lactones as potent dual activators of PPARγ and Nrf2 transcriptional factors.,  24  (16): [PMID:25027935] [10.1016/j.bmcl.2014.06.062]

2. 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