2-(3-((4-aminobutyl)amino)propyl)-7-(3-((2-methoxybenzyl)amino)propyl)benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetraone

ID: ALA4092588

PubChem CID: 137653213

Max Phase: Preclinical

Molecular Formula: C32H37N5O5

Molecular Weight: 571.68

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccccc1CNCCCN1C(=O)c2ccc3c4c(ccc(c24)C1=O)C(=O)N(CCCNCCCCN)C3=O

Standard InChI:  InChI=1S/C32H37N5O5/c1-42-26-9-3-2-8-21(26)20-35-17-7-19-37-31(40)24-12-10-22-27-23(11-13-25(28(24)27)32(37)41)30(39)36(29(22)38)18-6-16-34-15-5-4-14-33/h2-3,8-13,34-35H,4-7,14-20,33H2,1H3

Standard InChI Key:  OHFXFRJMJUJUJA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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  1 12  2  0
  5  2  2  0
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 24 38  1  0
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 40 41  1  0
 41 42  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4092588

   ---

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: 571.68

Molecular Weight (Monoisotopic): 571.2795

AlogP: 2.94

#Rotatable Bonds: 15

Polar Surface Area: 134.07

Molecular Species: BASE

HBA: 8

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 10.67

CX LogP: 1.59

CX LogD: -5.25

Aromatic Rings: 3

Heavy Atoms: 42

QED Weighted: 0.19

Np Likeness Score: -0.39

References

1. Milelli A, Marchetti C, Greco ML, Moraca F, Costa G, Turrini E, Catanzaro E, Betari N, Calcabrini C, Sissi C, Alcaro S, Fimognari C, Tumiatti V, Minarini A..  (2017)  Naphthalene diimide-polyamine hybrids as antiproliferative agents: Focus on the architecture of the polyamine chains.,  128  [PMID:28157593] [10.1016/j.ejmech.2017.01.025]

2. Recagni M, Greco ML, Milelli A, Minarini A, Zaffaroni N, Folini M, Sissi C..  (2019)  Distinct biological responses of metastatic castration resistant prostate cancer cells upon exposure to G-quadruplex interacting naphthalenediimide derivatives.,  177  [PMID:31158753] [10.1016/j.ejmech.2019.05.066]

Source

Source(1):

• Scientific Literature