(R)-6''-debromohamacanthin B

ID: ALA218941

PubChem CID: 16104847

Max Phase: Preclinical

Molecular Formula: C20H15BrN4O

Molecular Weight: 407.27

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1NC[C@@H](c2c[nH]c3ccccc23)N=C1c1c[nH]c2cc(Br)ccc12

Standard InChI:  InChI=1S/C20H15BrN4O/c21-11-5-6-13-15(9-23-17(13)7-11)19-20(26)24-10-18(25-19)14-8-22-16-4-2-1-3-12(14)16/h1-9,18,22-23H,10H2,(H,24,26)/t18-/m0/s1

Standard InChI Key:  YWUKMXVWWWYQPX-SFHVURJKSA-N

Molfile:  

     RDKit          2D

 26 30  0  0  0  0  0  0  0  0999 V2000
    1.1866   -0.8360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7938   -1.3886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5096   -0.9786    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5208   -0.0822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3427   -0.1734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8307    0.4918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4980    1.2486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6727    1.3362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1882    0.6700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3794   -1.0060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1509   -2.9996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1521   -3.8267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4374   -4.2396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4392   -2.5868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7239   -2.9959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7236   -3.8222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9377   -4.0773    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4521   -3.4086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9382   -2.7404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6835   -1.9557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1280   -1.7894    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1659   -0.3929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9740   -0.5629    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2329   -1.3489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0399   -1.5199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8668   -4.2387    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
 12 13  1  0
 13 16  2  0
  3  5  1  0
 15 14  2  0
 14 11  1  0
 15 16  1  0
  6  7  2  0
  4  1  1  0
  7  8  1  0
  8  9  2  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 15  1  0
  9  4  1  0
 19 20  1  0
 20 21  2  0
  1  2  2  0
 10  1  1  1
  4  5  2  0
  2  3  1  0
 20 24  1  0
 21 10  1  0
 10 22  1  0
 22 23  1  0
 23 24  1  0
 11 12  2  0
 24 25  2  0
  5  6  1  0
 12 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA218941

   (3R)-5-(6-bromo-1H-indol-3-yl)-3-(1H-indol-3-yl)-2,3-dihydro-1H-pyrazin-6-one

Molecule Features

Natural Product: Yes

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: 407.27

Molecular Weight (Monoisotopic): 406.0429

AlogP: 4.07

#Rotatable Bonds: 2

Polar Surface Area: 73.04

Molecular Species: NEUTRAL

HBA: 2

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.80

CX Basic pKa: 1.39

CX LogP: 3.72

CX LogD: 3.72

Aromatic Rings: 4

Heavy Atoms: 26

QED Weighted: 0.46

Np Likeness Score: 0.78

References

1. Bao B, Sun Q, Yao X, Hong J, Lee CO, Cho HY, Jung JH..  (2007)  Bisindole alkaloids of the topsentin and hamacanthin classes from a marine sponge Spongosorites sp.,  70  (1): [PMID:17253840] [10.1021/np060206z]

Source

Source(1):

• Scientific Literature