7-bromo-9-nitrocryptolepine hydrochloride

ID: ALA609689

PubChem CID: 46877427

Max Phase: Preclinical

Molecular Formula: C16H11BrClN3O2

Molecular Weight: 356.18

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[n+]1c2ccccc2cc2[n-]c3c([N+](=O)[O-])cc(Br)cc3c21.Cl

Standard InChI:  InChI=1S/C16H10BrN3O2.ClH/c1-19-13-5-3-2-4-9(13)6-12-16(19)11-7-10(17)8-14(20(21)22)15(11)18-12;/h2-8H,1H3;1H

Standard InChI Key:  JGKMDXNNJFNPRI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    7.4167   -1.2792    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.0167   -3.3167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0292   -4.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5167   -4.8167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2042   -4.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3042   -3.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5125   -3.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7250   -4.7375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3042   -4.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7292   -3.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8667   -3.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0167   -4.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7292   -4.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1750   -2.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9042   -4.6542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0625   -5.4875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3542   -2.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0250   -2.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0167   -1.8875    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    7.4417   -3.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4417   -4.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1542   -3.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1542   -4.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  7  2  0
  4  9  1  0
  5  3  1  0
  6  2  1  0
  7  6  1  0
  8  5  1  0
  9  6  2  0
 10  2  2  0
 11 17  1  0
 12 13  2  0
 13 10  1  0
 14  7  1  0
 15  8  1  0
 16  8  2  0
 17 14  2  0
 18  2  1  0
 19 17  1  0
 20 10  1  0
 21 13  1  0
 22 20  2  0
 23 22  1  0
  9 12  1  0
  3  4  1  0
 21 23  2  0
 11  5  2  0
M  CHG  4   2   1   4  -1   8   1  15  -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: 356.18

Molecular Weight (Monoisotopic): 354.9956

AlogP: 3.60

#Rotatable Bonds: 1

Polar Surface Area: 61.12

Molecular Species: ACID

HBA: 2

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.42

CX Basic pKa: ┄

CX LogP: -0.31

CX LogD: -1.00

Aromatic Rings: 4

Heavy Atoms: 22

QED Weighted: 0.30

Np Likeness Score: -0.25

References

1. Seville S, Phillips RM, Shnyder SD, Wright CW..  (2007)  Synthesis of cryptolepine analogues as potential bioreducible anticancer agents.,  15  (19): [PMID:17643990] [10.1016/j.bmc.2007.06.062]

Source

Source(1):

• Scientific Literature