8-chloro-9-nitrocryptolepine hydrochloride

ID: ALA609687

PubChem CID: 46877425

Max Phase: Preclinical

Molecular Formula: C16H11Cl2N3O2

Molecular Weight: 311.73

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[n+]1c2ccccc2cc2[n-]c3c([N+](=O)[O-])c(Cl)ccc3c21.Cl

Standard InChI:  InChI=1S/C16H10ClN3O2.ClH/c1-19-13-5-3-2-4-9(13)8-12-15(19)10-6-7-11(17)16(20(21)22)14(10)18-12;/h2-8H,1H3;1H

Standard InChI Key:  GFZVRYWAEIKWBG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    7.9792   -1.5542    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.8875   -3.1542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8917   -3.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3875   -4.6542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3792   -3.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1750   -3.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0750   -3.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5917   -4.5750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1750   -4.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6000   -3.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0417   -2.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8875   -4.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6000   -4.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7375   -3.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7750   -4.4917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9292   -5.3250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2250   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8917   -2.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9167   -3.0625    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.3125   -3.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3125   -4.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0250   -3.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0292   -4.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  5  2  0
  4  9  1  0
  5  6  1  0
  6  2  1  0
  7  3  1  0
  8  7  1  0
  9  6  2  0
 10  2  2  0
 11  5  1  0
 12 13  2  0
 13 10  1  0
 14 17  1  0
 15  8  1  0
 16  8  2  0
 17 11  2  0
 18  2  1  0
 19 14  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
 14  7  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: 311.73

Molecular Weight (Monoisotopic): 311.0462

AlogP: 3.49

#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: 6.29

CX Basic pKa: ┄

CX LogP: -0.48

CX LogD: -1.21

Aromatic Rings: 4

Heavy Atoms: 22

QED Weighted: 0.31

Np Likeness Score: -0.30

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