(1R,2R)-2-N-[16-(1'-pyridinium)-hexadecanoylamino]-1-(4''-nitrophenyl)-1,3-propandil bromide

ID: ALA406402

PubChem CID: 44456735

Max Phase: Preclinical

Molecular Formula: C30H46BrN3O4

Molecular Weight: 512.72

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@H](NC(=O)CCCCCCCCCCCCCCC[n+]1ccccc1)[C@H](O)c1ccc([N+](=O)[O-])cc1.[Br-]

Standard InChI:  InChI=1S/C30H45N3O4.BrH/c1-26(30(35)27-19-21-28(22-20-27)33(36)37)31-29(34)18-14-11-9-7-5-3-2-4-6-8-10-12-15-23-32-24-16-13-17-25-32;/h13,16-17,19-22,24-26,30,35H,2-12,14-15,18,23H2,1H3;1H/t26-,30+;/m1./s1

Standard InChI Key:  NXGUWJDMWCWWPJ-ABUDRPQHSA-N

Molfile:  

     RDKit          2D

 38 38  0  0  0  0  0  0  0  0999 V2000
   12.9940   -4.9238    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -1.9678   -4.5128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9696   -5.3405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2540   -5.7531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5401   -5.3397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5444   -4.5114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2567   -4.1004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1683   -4.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8857   -4.5074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5984   -4.0914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8904   -5.3315    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6036   -5.7395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3164   -5.3234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0297   -5.7314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7424   -5.3194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4598   -5.7274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1725   -5.3113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8857   -5.7234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5984   -5.3073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3118   -5.7152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0245   -5.3033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7419   -5.7113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4546   -5.2952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1679   -5.7073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8806   -5.2912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6073   -6.5636    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5962   -5.6997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3080   -5.2842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0236   -5.6928    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.0244   -6.5147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7392   -6.9233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4519   -6.5076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4452   -5.6793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7298   -5.2746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6881   -5.7485    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6888   -6.5726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3994   -5.3358    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1654   -3.2713    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  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
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 12 26  2  0
  2  3  2  0
 25 27  1  0
  3  4  1  0
 27 28  1  0
  4  5  2  0
 28 29  1  0
  5  6  1  0
 29 30  2  0
  6  7  2  0
 30 31  1  0
  7  2  1  0
 31 32  2  0
  6  8  1  0
 32 33  1  0
  8  9  1  0
 33 34  2  0
 34 29  1  0
  9 10  1  0
  9 11  1  1
 11 12  1  0
 35 36  2  0
 35 37  1  0
  3 35  1  0
 12 13  1  0
  8 38  1  1
 13 14  1  0
M  CHG  4   1  -1  29   1  35   1  37  -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: 512.72

Molecular Weight (Monoisotopic): 512.3483

AlogP: 6.58

#Rotatable Bonds: 20

Polar Surface Area: 96.35

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 13.65

CX Basic pKa: ┄

CX LogP: 3.02

CX LogD: 3.02

Aromatic Rings: 2

Heavy Atoms: 37

QED Weighted: 0.09

Np Likeness Score: -0.36

References

1. Szulc ZM, Mayroo N, Bai A, Bielawski J, Liu X, Norris JS, Hannun YA, Bielawska A..  (2008)  Novel analogs of D-e-MAPP and B13. Part 1: synthesis and evaluation as potential anticancer agents.,  16  (2): [PMID:17869115] [10.1016/j.bmc.2007.08.033]

Source

Source(1):

• Scientific Literature