2-fluoro-7,9-dinitrocryptolepine hydrochloride

ID: ALA609685

PubChem CID: 46877423

Max Phase: Preclinical

Molecular Formula: C16H10ClFN4O4

Molecular Weight: 340.27

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[n+]1c2ccc(F)cc2cc2[n-]c3c([N+](=O)[O-])cc([N+](=O)[O-])cc3c21.Cl

Standard InChI:  InChI=1S/C16H9FN4O4.ClH/c1-19-13-3-2-9(17)4-8(13)5-12-16(19)11-6-10(20(22)23)7-14(21(24)25)15(11)18-12;/h2-7H,1H3;1H

Standard InChI Key:  IPXFVAWEEIITDJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
    8.1042   -1.5750    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.6667   -3.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6750   -4.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8542   -4.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1625   -4.9042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1542   -3.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500   -3.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3667   -4.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9542   -4.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6625   -1.9750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3792   -3.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5167   -3.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0000   -2.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8167   -2.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3750   -4.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6667   -5.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5500   -4.7417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1417   -1.3042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0875   -3.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7042   -5.5750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8417   -1.8917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0875   -5.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6667   -2.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8042   -4.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8000   -3.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5167   -5.0542    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  3  6  2  0
  4  3  1  0
  5  9  1  0
  6  7  1  0
  7  2  1  0
  8  4  1  0
  9  7  2  0
 10 13  1  0
 11  2  2  0
 12 13  1  0
 13 14  2  0
 14  6  1  0
 15 11  1  0
 16 15  2  0
 17  8  1  0
 18 10  1  0
 19 11  1  0
 20  8  2  0
 21 10  2  0
 22 15  1  0
 23  2  1  0
 24 25  1  0
 25 19  2  0
 26 24  1  0
  9 16  1  0
  3  5  1  0
 22 24  2  0
 12  4  2  0
M  CHG  6   2   1   5  -1   8   1  10   1  17  -1  18  -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: 340.27

Molecular Weight (Monoisotopic): 340.0608

AlogP: 2.88

#Rotatable Bonds: 2

Polar Surface Area: 104.26

Molecular Species: ACID

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 5.91

CX Basic pKa: ┄

CX LogP: -1.00

CX LogD: -1.82

Aromatic Rings: 4

Heavy Atoms: 25

QED Weighted: 0.32

Np Likeness Score: -0.71

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