(2S,2'S)-(ethane-1,2-diylbis(azanediyl))bis(butane-2,1-diyl) bis(2-methylpropanoate)Dihydrochloride

ID: ALA5281822

Max Phase: Preclinical

Molecular Formula: C18H38Cl2N2O4

Molecular Weight: 344.50

Names and Identifiers

Canonical SMILES:  CC[C@@H](COC(=O)C(C)C)NCCN[C@@H](CC)COC(=O)C(C)C.Cl.Cl

Standard InChI:  InChI=1S/C18H36N2O4.2ClH/c1-7-15(11-23-17(21)13(3)4)19-9-10-20-16(8-2)12-24-18(22)14(5)6;;/h13-16,19-20H,7-12H2,1-6H3;2*1H/t15-,16-;;/m0../s1

Standard InChI Key:  VRWRJSZNPNLNNV-SXBSVMRRSA-N

Molfile:  

     RDKit          2D

 26 23  0  0  0  0  0  0  0  0999 V2000
    2.9356    1.8752    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.5726    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8581   -0.2061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1437    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1437    1.0314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8583    1.4439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8583    2.2691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5729    2.6814    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1437    2.6814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1437    3.5068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4290    2.2691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4290   -0.2062    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.2062    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4291   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4291   -1.0314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1437   -1.4439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1437   -2.2691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8584   -2.6817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5729   -2.2691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8584   -3.5068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4291   -2.6817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1437    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8584   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0027    2.3663    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  3  4  1  0
  4  5  1  1
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
  9 11  1  0
  4 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  1
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 19 23  2  0
 16 24  1  0
 24 25  1  0
M  END

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 344.50

Molecular Weight (Monoisotopic): 344.2675

AlogP: 2.12

#Rotatable Bonds: 13

Polar Surface Area: 76.66

Molecular Species: BASE

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.08

CX LogP: 3.31

CX LogD: 1.60

Aromatic Rings: ┄

Heavy Atoms: 24

QED Weighted: 0.39

Np Likeness Score: 0.19

References

1. Larsen EM, Stephens DC, Clarke NH, Johnson RJ..  (2017)  Ester-prodrugs of ethambutol control its antibacterial activity and provide rapid screening for mycobacterial hydrolase activity.,  27  (19): [PMID:28882482] [10.1016/j.bmcl.2017.08.057]

Source

Source(1):

• Scientific Literature