5H-dibenzo[b,h]carbazole-5,7,12,13(6H)-tetraone

ID: ALA4554800

PubChem CID: 14024996

Max Phase: Preclinical

Molecular Formula: C20H9NO4

Molecular Weight: 327.30

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=c1c2ccccc2c(=O)c2c1[nH]c1c(=O)c3ccccc3c(=O)c12

Standard InChI:  InChI=1S/C20H9NO4/c22-17-9-5-1-3-7-11(9)19(24)15-13(17)14-16(21-15)20(25)12-8-4-2-6-10(12)18(14)23/h1-8,21H

Standard InChI Key:  BHCZAWBMHNLMRV-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 25 29  0  0  0  0  0  0  0  0999 V2000
    6.5844  -17.1309    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9817  -15.8470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2460  -16.6324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0539  -16.7953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5253  -15.2243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9060  -16.6528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1534  -15.8657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5986  -15.2614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1039  -16.8354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3389  -15.3902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6024  -16.1730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4104  -16.3351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9560  -15.7151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6878  -14.9304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8803  -14.7722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5461  -16.2253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7955  -15.4415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2420  -14.8355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4388  -15.0122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1921  -15.8003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7474  -16.4030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8468  -14.4696    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8562  -17.6275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3186  -17.5818    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2594  -14.4382    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0
  1  3  1  0
  2  7  1  0
  2  3  2  0
  2  5  1  0
  3  4  1  0
  4 11  1  0
 10  5  1  0
  6  7  2  0
  6  9  1  0
  7  8  1  0
  8 17  1  0
 16  9  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
  8 22  2  0
  9 23  2  0
  4 24  2  0
  5 25  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4554800

   12-Azapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(13),2(11),4,6,8,15,17,19-octaene-3,10,14,21-tetrone

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 327.30

Molecular Weight (Monoisotopic): 327.0532

AlogP: 1.94

#Rotatable Bonds: ┄

Polar Surface Area: 84.07

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 5.16

CX Basic pKa: ┄

CX LogP: 2.78

CX LogD: 1.89

Aromatic Rings: 5

Heavy Atoms: 25

QED Weighted: 0.47

Np Likeness Score: 0.12

References

1. Hammons JC, Trzoss L, Jimenez PC, Hirata AS, Costa-Lotufo LV, La Clair JJ, Fenical W..  (2019)  Advance of Seriniquinone Analogues as Melanoma Agents.,  10  (2): [PMID:30783501] [10.1021/acsmedchemlett.8b00391]

Source

Source(1):

• Scientific Literature