(E)-15-(N-4-Biphenyl)sophoridinic imine

ID: ALA4244448

PubChem CID: 145985974

Max Phase: Preclinical

Molecular Formula: C27H33N3

Molecular Weight: 399.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  c1ccc(-c2ccc(/N=C3\CCC[C@@H]4[C@H]5CCCN6CCC[C@H](CN34)[C@@H]56)cc2)cc1

Standard InChI:  InChI=1S/C27H33N3/c1-2-7-20(8-3-1)21-13-15-23(16-14-21)28-26-12-4-11-25-24-10-6-18-29-17-5-9-22(27(24)29)19-30(25)26/h1-3,7-8,13-16,22,24-25,27H,4-6,9-12,17-19H2/b28-26+/t22-,24-,25-,27+/m1/s1

Standard InChI Key:  MPXZDKAUABMFJK-VCJXSUFBSA-N

Molfile:  

     RDKit          2D

 34 39  0  0  0  0  0  0  0  0999 V2000
    1.3207  -25.2297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3207  -26.0469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0260  -26.4514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7278  -26.0469    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4299  -26.4562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1399  -26.0529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1434  -25.2357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0260  -24.8170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7295  -25.2327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4373  -24.8336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0303  -24.0021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7443  -23.6014    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4502  -24.0205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1621  -23.6210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1745  -22.8008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4687  -22.3817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7505  -22.7827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0473  -22.3664    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7240  -24.4126    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4297  -25.6507    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1520  -24.4291    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0182  -25.6342    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0562  -21.5493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7701  -21.1515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7793  -20.3352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0756  -19.9181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3611  -20.3233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3553  -21.1383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0836  -19.1015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7968  -18.7003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8049  -17.8839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1006  -17.4677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3867  -17.8739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3820  -18.6889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  8  1  0
  2  3  1  0
  3  4  1  0
  9  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7 10  1  0
  8  9  1  0
  8 11  1  0
  9 10  1  0
 10 13  1  0
 12 11  1  0
 12 13  1  0
 12 17  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
  9 19  1  6
 10 20  1  6
 13 21  1  1
  8 22  1  1
 18 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 34 29  1  0
 26 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4244448

   ---

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: 399.58

Molecular Weight (Monoisotopic): 399.2674

AlogP: 5.74

#Rotatable Bonds: 2

Polar Surface Area: 18.84

Molecular Species: BASE

HBA: 2

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 8.89

CX LogP: 4.93

CX LogD: 2.66

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.64

Np Likeness Score: 0.29

References

1. Xu Y, Jing D, Chen R, Rashid HU, Jiang J, Liu X, Wang L, Xie P..  (2018)  Design, synthesis and evaluation of novel sophoridinic imine derivatives containing conjugated planar structure as potent anticancer agents.,  26  (14): [PMID:30007563] [10.1016/j.bmc.2018.07.001]

Source

Source(1):

• Scientific Literature