2-(2,2-dichloroacetamido)-N,N-bis(2-(2,2-dichloroacetamido)ethyl)-N-methylethanaminium trifluoroacetate

ID: ALA3752113

PubChem CID: 127037426

Max Phase: Preclinical

Molecular Formula: C15H21Cl6F3N4O5

Molecular Weight: 494.05

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[N+](CCNC(=O)C(Cl)Cl)(CCNC(=O)C(Cl)Cl)CCNC(=O)C(Cl)Cl.O=C([O-])C(F)(F)F

Standard InChI:  InChI=1S/C13H20Cl6N4O3.C2HF3O2/c1-23(5-2-20-11(24)8(14)15,6-3-21-12(25)9(16)17)7-4-22-13(26)10(18)19;3-2(4,5)1(6)7/h8-10H,2-7H2,1H3,(H2-,20,21,22,24,25,26);(H,6,7)

Standard InChI Key:  QXEAVDNMVGHPCV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 33 31  0  0  0  0  0  0  0  0999 V2000
   20.6999   -2.6277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3999   -1.8777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3604   -2.4773    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   19.3999   -0.6777    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   18.3607   -1.2775    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   20.6999   -3.8277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.7393   -2.0280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3999    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0999    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7999    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5000    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9000    0.7500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3000    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2606    0.1503    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.3000    1.9500    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.6000   -1.2000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7999   -1.5007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5007   -2.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5007   -3.7528    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2014   -4.5040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1620   -3.9044    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2014   -6.0049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1625   -6.6055    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.2408   -6.6045    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.7999    1.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6999    0.7500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.9999    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2999    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3393    0.1503    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   14.2999    1.9500    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   12.9999   -1.2000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  1  6  1  0
  1  7  2  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
 15 17  1  0
 14 18  2  0
 10 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 24 26  1  0
 10 27  1  0
  8 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 30 32  1  0
 29 33  2  0
M  CHG  2   6  -1  10   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: 494.05

Molecular Weight (Monoisotopic): 490.9739

AlogP: 1.19

#Rotatable Bonds: 12

Polar Surface Area: 87.30

Molecular Species: NEUTRAL

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.67

CX Basic pKa: ┄

CX LogP: -3.06

CX LogD: -1.38

Aromatic Rings: ┄

Heavy Atoms: 26

QED Weighted: 0.28

Np Likeness Score: 0.04

References

1. Trapella C, Voltan R, Melloni E, Tisato V, Celeghini C, Bianco S, Fantinati A, Salvadori S, Guerrini R, Secchiero P, Zauli G..  (2016)  Design, Synthesis, and Biological Characterization of Novel Mitochondria Targeted Dichloroacetate-Loaded Compounds with Antileukemic Activity.,  59  (1): [PMID:26653539] [10.1021/acs.jmedchem.5b01165]

Source

Source(1):

• Scientific Literature