N,N'-(2,3-dihydroxylbenzyl)-N,N,N',N'-tetramethyl-1,10-decanediamine dibromide

ID: ALA138569

PubChem CID: 204063

Max Phase: Preclinical

Molecular Formula: C28H46Br2N2O4

Molecular Weight: 474.69

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[N+](C)(CCCCCCCCCC[N+](C)(C)Cc1cccc(O)c1O)Cc1cccc(O)c1O.[Br-].[Br-]

Standard InChI:  InChI=1S/C28H44N2O4.2BrH/c1-29(2,21-23-15-13-17-25(31)27(23)33)19-11-9-7-5-6-8-10-12-20-30(3,4)22-24-16-14-18-26(32)28(24)34;;/h13-18H,5-12,19-22H2,1-4H3,(H2-2,31,32,33,34);2*1H

Standard InChI Key:  OMFHNVXGGZZORH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 36 35  0  0  0  0  0  0  0  0999 V2000
    7.2417   -1.7417    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    7.4917   -4.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3542   -1.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8792   -1.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0042   -3.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9792   -3.1917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8750   -0.6042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3542   -0.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9750   -3.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5250   -4.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8792   -2.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0042   -3.1917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4000   -1.5042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4042   -2.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0417   -3.7917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8417   -1.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4875   -4.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3792   -3.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -0.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0042   -4.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8417   -2.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4625    0.0333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8167   -2.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4917   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3417    0.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5250   -4.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3542   -2.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7750   -1.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0792   -2.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5792   -2.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1792   -2.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4792   -2.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3750   -1.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6750   -1.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2750   -1.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4042   -0.3750    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  3  8  1  0
  4  3  2  0
  5  2  1  0
  6  9  1  0
  7 19  1  0
  8  7  1  0
  9  2  1  0
 10  5  2  0
 11  4  1  0
 12  5  1  0
 13  4  1  0
 14 11  1  0
 15 10  1  0
 16  3  1  0
 17  2  2  0
 18  6  1  0
 19 28  1  0
 20 17  1  0
 21 16  2  0
 22  7  1  0
 23  6  1  0
 24  6  1  0
 25  7  1  0
 26 20  2  0
 27 21  1  0
 28 33  1  0
 29 18  1  0
 30 31  1  0
 31 32  1  0
 32 29  1  0
 33 34  1  0
 34 35  1  0
 35 30  1  0
 10 26  1  0
 11 27  2  0
M  CHG  4   1  -1   6   1   7   1  36  -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: 474.69

Molecular Weight (Monoisotopic): 474.3447

AlogP: 5.48

#Rotatable Bonds: 15

Polar Surface Area: 80.92

Molecular Species: NEUTRAL

HBA: 4

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.54

CX Basic pKa: ┄

CX LogP: -2.64

CX LogD: -1.09

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.16

Np Likeness Score: 0.32

References

1. Gu Y, Lee H, Hudson RA..  (1994)  Bis-catechol-substituted redox-reactive analogues of hexamethonium and decamethonium: stimulated affinity-dependent reactivity through iron peroxide catalysis.,  37  (25): [PMID:7996555] [10.1021/jm00051a021]

2. Cai S, Mukherjee J, Tillekeratne LM, Hudson RA, Kirchhoff JR..  (2007)  Inhibition of choline transport by redox-active cholinomimetic bis-catechol reagents.,  15  (22): [PMID:17827016] [10.1016/j.bmc.2007.07.041]

Source

Source(1):

• Scientific Literature