2,8-Dibromo-5-formyl-3,3-dimethyl-7-methoxypyrano[3,2-a]carbazole

ID: ALA1818864

PubChem CID: 54768539

Max Phase: Preclinical

Molecular Formula: C19H17Br2NO3

Molecular Weight: 467.16

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc2[nH]c3c4c(c(C=O)cc3c2cc1Br)OC(C)(C)C(Br)C4

Standard InChI:  InChI=1S/C19H17Br2NO3/c1-19(2)16(21)6-12-17-11(4-9(8-23)18(12)25-19)10-5-13(20)15(24-3)7-14(10)22-17/h4-5,7-8,16,22H,6H2,1-3H3

Standard InChI Key:  BBAKSUBITWVQPC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
   16.6604  -22.2446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3772  -21.8361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6651  -21.4196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7529  -20.1428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5630  -19.9976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0960  -20.6263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8144  -21.4034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4663  -21.9114    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.9221  -20.6541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1499  -21.4459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9480  -21.6430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5189  -21.0493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2864  -20.2556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4888  -20.0623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2218  -19.5114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5030  -18.7357    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0008  -21.5523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4707  -20.9207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6632  -21.0631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9093  -22.4683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7233  -22.3264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6270  -23.2436    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   23.3203  -21.2457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.5508  -22.0380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8558  -19.6586    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
 11 12  2  0
  6  7  1  0
 12 13  1  0
  3  2  1  0
 13 14  2  0
 14  9  1  0
  4 15  1  0
  4 18  2  0
 15 16  2  0
 17 18  1  0
  7  8  1  0
  8 10  1  0
  9  6  1  0
 17  7  2  0
  2  1  1  0
 17 21  1  0
 18 19  1  0
 19  2  1  0
  2 20  1  0
 20 21  1  0
  9 10  2  0
 20 22  1  0
  6  5  2  0
 12 23  1  0
 10 11  1  0
 23 24  1  0
  5  4  1  0
 13 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1818864

   2,8-dibromo-9-methoxy-3,3-dimethyl-2,11-dihydro-1H-pyrano[3,2-a]carbazole-5-carbaldehyde

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: 467.16

Molecular Weight (Monoisotopic): 464.9575

AlogP: 5.38

#Rotatable Bonds: 2

Polar Surface Area: 51.32

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.90

CX LogD: 4.90

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.41

Np Likeness Score: 1.29

References

1. Thongthoom T, Promsuwan P, Yenjai C..  (2011)  Synthesis and cytotoxic activity of the heptaphylline and 7-methoxyheptaphylline series.,  46  (9): [PMID:21641693] [10.1016/j.ejmech.2011.05.041]

Source

Source(1):

• Scientific Literature