Dispyrin B

ID: ALA5174997

PubChem CID: 168273029

Max Phase: Preclinical

Molecular Formula: C18H22Br3N3O2

Molecular Weight: 552.11

Names and Identifiers

Canonical SMILES:  CN(C)CCCOc1c(Br)cc(CCNC(=O)c2cc(Br)c[nH]2)cc1Br

Standard InChI:  InChI=1S/C18H22Br3N3O2/c1-24(2)6-3-7-26-17-14(20)8-12(9-15(17)21)4-5-22-18(25)16-10-13(19)11-23-16/h8-11,23H,3-7H2,1-2H3,(H,22,25)

Standard InChI Key:  GJQHOBZVFIFOHW-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 26 27  0  0  0  0  0  0  0  0999 V2000
   -4.0452   -1.6861    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8525   -1.8557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2634   -1.1402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7098   -0.5284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9570   -0.8659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2637   -0.4181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3050    0.4059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5296   -0.7944    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8364   -0.3468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1021   -0.7231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4091   -0.2753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4500    0.5487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2413    0.9944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9758    0.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0184   -0.2019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3283   -0.6533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6905    1.0306    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4049    0.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1196    1.0306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8342    0.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5488    1.0306    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2634    0.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5488    1.8557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7330   -0.6143    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.2413    1.8196    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -6.0836   -1.0520    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  1  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 12 11  2  0
 13 12  1  0
 14 13  2  0
 15 14  1  0
 16 15  2  0
 11 16  1  0
 14 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 15 24  1  0
 13 25  1  0
  3 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5174997

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 552.11

Molecular Weight (Monoisotopic): 548.9262

AlogP: 4.61

#Rotatable Bonds: 9

Polar Surface Area: 57.36

Molecular Species: BASE

HBA: 3

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 9.26

CX LogP: 4.29

CX LogD: 2.43

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.45

Np Likeness Score: -0.55

References

1. Freire VF, Gubiani JR, Spencer TM, Hajdu E, Ferreira AG, Ferreira DAS, de Castro Levatti EV, Burdette JE, Camargo CH, Tempone AG, Berlinck RGS..  (2022)  Feature-Based Molecular Networking Discovery of Bromopyrrole Alkaloids from the Marine Sponge Agelas dispar.,  85  (5.0): [PMID:35427139] [10.1021/acs.jnatprod.2c00094]

Source

Source(1):

• Scientific Literature