2-Carboxy-4-hexadecanoyloxy-1,1-dimethyl-pyrrolidinium chloride

ID: ALA352878

PubChem CID: 44382080

Max Phase: Preclinical

Molecular Formula: C23H44ClNO4

Molecular Weight: 398.61

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCCCCCCCCC(=O)O[C@@H]1C[C@@H](C(=O)O)[N+](C)(C)C1.[Cl-]

Standard InChI:  InChI=1S/C23H43NO4.ClH/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-22(25)28-20-18-21(23(26)27)24(2,3)19-20;/h20-21H,4-19H2,1-3H3;1H/t20-,21+;/m1./s1

Standard InChI Key:  FZHSOHBAZNYLEK-BHDTVMLSSA-N

Molfile:  

     RDKit          2D

 29 28  0  0  0  0  0  0  0  0999 V2000
    3.0250   -7.1542    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.3292   -6.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9792   -5.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6292   -6.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6875   -5.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9792   -4.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6875   -4.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2042   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0625   -4.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2792   -5.6875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6417   -3.8542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0542   -6.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3292   -6.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6292   -6.8125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9042   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0292   -5.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0208  -11.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1500  -11.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8542   -6.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5500   -7.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6792   -7.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3750   -8.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5042   -8.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2000   -9.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6708   -9.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9833  -10.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8458  -10.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7250   -6.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3333  -12.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  3  4  1  1
  5  2  1  0
  6  3  1  0
  7  5  1  0
  8  9  1  0
  7  9  1  6
 10  4  2  0
 11  8  2  0
 12  2  1  0
 13  2  1  0
 14  4  1  0
 15  8  1  0
 16 15  1  0
 17 18  1  0
 18 27  1  0
 19 28  1  0
 20 19  1  0
 21 20  1  0
 22 21  1  0
 23 22  1  0
 24 23  1  0
 25 24  1  0
 26 25  1  0
 27 26  1  0
 28 16  1  0
 29 17  1  0
  6  7  1  0
M  CHG  2   1  -1   2   1
M  END

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: 398.61

Molecular Weight (Monoisotopic): 398.3265

AlogP: 5.31

#Rotatable Bonds: 16

Polar Surface Area: 63.60

Molecular Species: ACID

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 2.08

CX Basic pKa: ┄

CX LogP: 1.90

CX LogD: 2.67

Aromatic Rings: ┄

Heavy Atoms: 28

QED Weighted: 0.22

Np Likeness Score: 1.10

References

1. Woster PM, Murray WJ..  (1986)  Synthesis and biological evaluation of cyclic analogues of 1-carnitine as potential agents in the treatment of myocardial ischemia.,  29  (5): [PMID:3084787] [10.1021/jm00155a045]

Source

Source(1):

• Scientific Literature