Dibromoageliferin

ID: ALA5178946

PubChem CID: 15816052

Max Phase: Preclinical

Molecular Formula: C22H22Br4N10O2

Molecular Weight: 778.10

Names and Identifiers

Canonical SMILES:  Nc1nc([C@@H]2c3nc(N)[nH]c3C[C@H](CNC(=O)c3cc(Br)c(Br)[nH]3)[C@H]2CNC(=O)c2cc(Br)c(Br)[nH]2)c[nH]1

Standard InChI:  InChI=1S/C22H22Br4N10O2/c23-9-2-12(32-17(9)25)19(37)29-4-7-1-11-16(36-22(28)34-11)15(14-6-31-21(27)35-14)8(7)5-30-20(38)13-3-10(24)18(26)33-13/h2-3,6-8,15,32-33H,1,4-5H2,(H,29,37)(H,30,38)(H3,27,31,35)(H3,28,34,36)/t7-,8-,15-/m1/s1

Standard InChI Key:  VOGBZMFIZJPYAJ-KDZIRCDLSA-N

Molfile:  

 
     RDKit          2D

 38 42  0  0  0  0  0  0  0  0999 V2000
    0.7138    1.0310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4282    1.4435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1427    1.0310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1427    0.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4282   -0.2065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7138    0.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0004   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0004   -1.0310    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7147   -1.4435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7147   -2.2683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0004   -2.6806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1858   -3.5018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9869   -3.5826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3188   -2.8231    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3991   -4.2970    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.3973   -4.0850    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -1.4290   -1.0310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9256   -0.0398    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4176    0.6276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9468    1.2810    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2424    0.6276    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4282    2.2683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7140    2.6806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8993    3.5018    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7004    3.5826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0324    2.8231    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1128    4.2970    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0004    1.4434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7147    1.0310    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4290    1.4434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1432    1.0310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1432    0.2063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9471   -0.0437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4176    0.6095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9257    1.2768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2424    0.6095    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -1.4290    2.2682    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1605   -0.8404    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  6  5  1  0
  1  6  1  0
  6  7  1  6
  7  8  1  0
  8  9  1  0
  9 10  1  0
 11 10  2  0
 11 12  1  0
 12 13  2  0
 14 13  1  0
 10 14  1  0
 13 15  1  0
 12 16  1  0
  9 17  2  0
  4 18  1  0
 18 19  1  0
 20 19  2  0
  3 20  1  0
 19 21  1  0
  2 22  1  6
 23 22  2  0
 23 24  1  0
 24 25  1  0
 26 25  2  0
 22 26  1  0
 25 27  1  0
  1 28  1  1
 28 29  1  0
 29 30  1  0
 30 31  1  0
 32 31  1  0
 32 33  1  0
 33 34  2  0
 35 34  1  0
 31 35  2  0
 34 36  1  0
 30 37  2  0
 33 38  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5178946

   N-[[(5S,6R,7R)-2-amino-7-(2-amino-1H-imidazol-5-yl)-6-[[(4,5-dibromo-1H-pyrrole-2-carbonyl)amino]methyl]-4,5,6,7-tetrahydro-3H-benzimidazol-5-yl]methyl]-4,5-dibromo-1H-pyrrole-2-carboxamide

Molecule Features

Natural Product: Yes

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: 778.10

Molecular Weight (Monoisotopic): 773.8661

AlogP: 3.78

#Rotatable Bonds: 7

Polar Surface Area: 199.18

Molecular Species: BASE

HBA: 6

HBD: 8

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 10

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 11.68

CX Basic pKa: 8.91

CX LogP: 2.06

CX LogD: -0.04

Aromatic Rings: 4

Heavy Atoms: 38

QED Weighted: 0.14

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