Dispyrin C

ID: ALA5202838

PubChem CID: 168293602

Max Phase: Preclinical

Molecular Formula: C18H22Br2IN3O2

Molecular Weight: 599.11

Names and Identifiers

Canonical SMILES:  CN(C)CCCOc1c(Br)cc(CCNC(=O)c2cc(Br)c[nH]2)cc1I

Standard InChI:  InChI=1S/C18H22Br2IN3O2/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:  GZVXVVWGDJWASJ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 26 27  0  0  0  0  0  0  0  0999 V2000
   -3.6330   -1.6862    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4403   -1.8559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8512   -1.1403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2977   -0.5285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5447   -0.8659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8515   -0.4181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8927    0.4059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1172   -0.7946    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4240   -0.3468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6897   -0.7232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0034   -0.2754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0374    0.5488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6539    0.9945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3885    0.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4311   -0.2019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7409   -0.6535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1031    1.0306    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8178    0.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5325    1.0306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2471    0.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9618    1.0306    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6764    0.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9618    1.8559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1457   -0.6145    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
    0.6539    1.8197    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -5.6764   -1.1403    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:

   

   ALA5202838

   ---

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: 599.11

Molecular Weight (Monoisotopic): 596.9123

AlogP: 4.45

#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: 4.45

CX LogD: 2.59

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.33

Np Likeness Score: -0.66

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