(3R,5S)-cis-3,4-Dihydrohamacanthin B

ID: ALA4534089

PubChem CID: 12192939

Max Phase: Preclinical

Molecular Formula: C20H16Br2N4O

Molecular Weight: 488.18

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C1NC[C@H](c2c[nH]c3cc(Br)ccc23)N[C@@H]1c1c[nH]c2cc(Br)ccc12

Standard InChI:  InChI=1S/C20H16Br2N4O/c21-10-1-3-12-14(7-23-16(12)5-10)18-9-25-20(27)19(26-18)15-8-24-17-6-11(22)2-4-13(15)17/h1-8,18-19,23-24,26H,9H2,(H,25,27)/t18-,19-/m1/s1

Standard InChI Key:  OXVVLWOQGFZGEO-RTBURBONSA-N

Molfile:  

 
     RDKit          2D

 27 31  0  0  0  0  0  0  0  0999 V2000
   22.5434  -20.7822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5395  -21.5971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2513  -20.3756    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.2435  -22.0112    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.9543  -21.6074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9582  -20.7867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8394  -20.3682    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.5370  -23.0074    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.7401  -22.8339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6612  -22.0185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4063  -21.6900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6638  -20.9163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4660  -20.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0107  -21.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7532  -22.1371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9511  -22.3034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9370  -22.9769    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.7362  -22.8136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8286  -22.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0851  -21.6638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8371  -20.8851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0373  -20.7087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4883  -21.3138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7363  -22.0925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5332  -22.2660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6885  -21.1374    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   27.8112  -21.1991    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  3  6  1  0
  1  7  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
  8 16  1  0
 11 16  2  0
  5 10  1  6
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 17 25  1  0
 20 25  2  0
 23 26  1  0
  2 19  1  6
 14 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4534089

   (3R,5S)-3,5-bis(6-bromo-1H-indol-3-yl)piperazin-2-one

Molecule Features

Natural Product: Yes

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: 488.18

Molecular Weight (Monoisotopic): 485.9691

AlogP: 4.68

#Rotatable Bonds: 2

Polar Surface Area: 72.71

Molecular Species: NEUTRAL

HBA: 2

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.52

CX Basic pKa: 5.70

CX LogP: 3.99

CX LogD: 3.98

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.33

Np Likeness Score: 0.73

References

1. Kim A, Kim MJ, Noh TH, Hong J, Liu Y, Wei X, Jung JH..  (2016)  Synthesis and antibacterial evaluation of hamacanthin B analogues.,  26  (20): [PMID:27614413] [10.1016/j.bmcl.2016.08.095]

Source

Source(1):

• Scientific Literature