7-bromo-8-nitrocryptolepine hydrochloride

ID: ALA609688

PubChem CID: 46877426

Max Phase: Preclinical

Molecular Formula: C16H11BrClN3O2

Molecular Weight: 356.18

Molecule Type: Small molecule

Names and Identifiers

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

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

Standard InChI Key:  DDTJJPQSSJQQBU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    1.6074  -15.4515    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.6571  -19.4212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3722  -19.0086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3693  -18.1793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6553  -17.7709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0567  -19.0090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0543  -18.1848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7659  -17.7725    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7664  -19.4192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4785  -19.0107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4804  -18.1795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2684  -19.2692    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7586  -18.5981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2739  -17.9274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6105  -17.1766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4327  -17.0900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9174  -17.7606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5797  -18.5177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7629  -16.9488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7351  -17.6735    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0714  -16.9215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2191  -18.3416    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7686  -16.3380    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
 11 14  1  0
 13 12  1  0
 12 10  1  0
 13 14  2  0
  6  2  1  0
  6  7  1  0
  3  4  1  0
  7  8  2  0
  8 11  1  0
 13 18  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 10  9  1  0
  8 19  1  0
  9  6  2  0
 10 11  2  0
  4  5  2  0
 20 21  1  0
 20 22  2  0
 17 20  1  0
  5  7  1  0
 16 23  1  0
M  CHG  4   8   1  12  -1  20   1  21  -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: NEUTRAL

HBA: 2

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.13

CX Basic pKa: ┄

CX LogP: -0.31

CX LogD: -0.68

Aromatic Rings: 4

Heavy Atoms: 22

QED Weighted: 0.30

Np Likeness Score: -0.17

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