2N-{3-[4-(4-bromo-1H-2-pyrrolylcarboxamido)butylamino]propyl}-4-bromo-1H-2-pyrrolecarboxamide

ID: ALA109490

Chembl Id: CHEMBL109490

PubChem CID: 44339649

Max Phase: Preclinical

Molecular Formula: C17H23Br2N5O2

Molecular Weight: 489.21

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NCCCCNCCCNC(=O)c1cc(Br)c[nH]1)c1cc(Br)c[nH]1

Standard InChI:  InChI=1S/C17H23Br2N5O2/c18-12-8-14(23-10-12)16(25)21-6-2-1-4-20-5-3-7-22-17(26)15-9-13(19)11-24-15/h8-11,20,23-24H,1-7H2,(H,21,25)(H,22,26)

Standard InChI Key:  YLDAAMRRCXMEJK-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA109490

   4-bromo-N-[4-[3-[(4-bromo-1H-pyrrole-2-carbonyl)amino]propylamino]butyl]-1H-pyrrole-2-carboxamide

Molecule Features

Natural Product: No

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: 489.21

Molecular Weight (Monoisotopic): 487.0218

AlogP: 2.79

#Rotatable Bonds: 11

Polar Surface Area: 101.81

Molecular Species: BASE

HBA: 3

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.83

CX Basic pKa: 10.18

CX LogP: 1.73

CX LogD: -0.92

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.31

Np Likeness Score: -0.42

References

1. Behrens C, Christoffersen MW, Gram L, Nielsen PH.  (1997)  A convenient synthesis of pseudoceratidine and three analogs for biological evaluation,  7  (3): [10.1016/S0960-894X(96)00622-1]

2. Parra LLL, Bertonha AF, Severo IRM, Aguiar ACC, de Souza GE, Oliva G, Guido RVC, Grazzia N, Costa TR, Miguel DC, Gadelha FR, Ferreira AG, Hajdu E, Romo D, Berlinck RGS..  (2018)  Isolation, Derivative Synthesis, and Structure-Activity Relationships of Antiparasitic Bromopyrrole Alkaloids from the Marine Sponge Tedania brasiliensis.,  81  (1): [PMID:29297684] [10.1021/acs.jnatprod.7b00876]

Source

Source(1):

• Scientific Literature