2-fluoro-9-nitrocryptolepine hydrochloride

ID: ALA609430

PubChem CID: 46877422

Max Phase: Preclinical

Molecular Formula: C16H11ClFN3O2

Molecular Weight: 295.27

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[n+]1c2ccc(F)cc2cc2[n-]c3c([N+](=O)[O-])cccc3c21.Cl

Standard InChI:  InChI=1S/C16H10FN3O2.ClH/c1-19-13-6-5-10(17)7-9(13)8-12-16(19)11-3-2-4-14(20(21)22)15(11)18-12;/h2-8H,1H3;1H

Standard InChI Key:  LKVQFHVIMGWJGW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    8.1917   -1.7750    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.6125   -2.9417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6167   -3.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1042   -4.4417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8917   -3.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1042   -3.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7917   -3.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3167   -4.3625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9000   -4.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3167   -3.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3167   -4.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6125   -4.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4917   -4.2792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0292   -2.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6542   -5.1125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0292   -4.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6125   -2.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7500   -4.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7667   -2.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4542   -2.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7417   -3.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4625   -4.5917    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.9417   -2.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  6  2  0
  4  9  1  0
  5  2  1  0
  6  5  1  0
  7  3  1  0
  8  7  1  0
  9  5  2  0
 10  2  2  0
 11 10  1  0
 12 11  2  0
 13  8  1  0
 14 10  1  0
 15  8  2  0
 16 11  1  0
 17  2  1  0
 18 21  1  0
 19  6  1  0
 20 23  1  0
 21 14  2  0
 22 18  1  0
 23 19  2  0
  9 12  1  0
  3  4  1  0
 16 18  2  0
 20  7  2  0
M  CHG  4   2   1   4  -1   8   1  13  -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: 295.27

Molecular Weight (Monoisotopic): 295.0757

AlogP: 2.98

#Rotatable Bonds: 1

Polar Surface Area: 61.12

Molecular Species: NEUTRAL

HBA: 2

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.54

CX Basic pKa: ┄

CX LogP: -0.94

CX LogD: -1.58

Aromatic Rings: 4

Heavy Atoms: 22

QED Weighted: 0.31

Np Likeness Score: -0.68

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