8-chloro-7-nitrocryptolepine hydrochloride

ID: ALA609686

PubChem CID: 46877424

Max Phase: Preclinical

Molecular Formula: C16H11Cl2N3O2

Molecular Weight: 311.73

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[n+]1c2ccccc2cc2[n-]c3cc(Cl)c([N+](=O)[O-])cc3c21.Cl

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

Standard InChI Key:  OQFBXYRBTIVTOT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    8.0500   -1.7917    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.8250   -3.7375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3167   -3.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1042   -4.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3167   -5.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1542   -3.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8292   -4.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8167   -2.3042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1125   -4.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9792   -3.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5292   -4.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6667   -3.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0042   -4.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8250   -5.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5292   -4.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000   -1.6375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0000   -2.2167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8250   -2.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8542   -3.6417    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.2417   -3.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2417   -5.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9542   -4.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9625   -4.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0
  4  2  1  0
  5  9  1  0
  6 10  2  0
  7  3  2  0
  8  6  1  0
  9  4  2  0
 10  3  1  0
 11  2  2  0
 12  6  1  0
 13  7  1  0
 14 15  2  0
 15 11  1  0
 16  8  1  0
 17  8  2  0
 18  2  1  0
 19 12  1  0
 20 11  1  0
 21 15  1  0
 22 20  2  0
 23 22  1  0
  9 14  1  0
  7  5  1  0
 21 23  2  0
 12 13  2  0
M  CHG  4   2   1   5  -1   8   1  16  -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: NEUTRAL

HBA: 2

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.26

CX Basic pKa: ┄

CX LogP: -0.48

CX LogD: -0.53

Aromatic Rings: 4

Heavy Atoms: 22

QED Weighted: 0.31

Np Likeness Score: -0.38

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