N-(4-amino-butyl)-N-(4-{[4-(4-amino-butylamino)butylamino]-methyl}benzyl)butane-1,4-diamine trihydrochloride salt

ID: ALA557403

Chembl Id: CHEMBL557403

PubChem CID: 45266005

Max Phase: Preclinical

Molecular Formula: C24H49ClN6

Molecular Weight: 420.69

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cl.NCCCCNCCCCNCc1ccc(CNCCCCNCCCCN)cc1

Standard InChI:  InChI=1S/C24H48N6.ClH/c25-13-1-3-15-27-17-5-7-19-29-21-23-9-11-24(12-10-23)22-30-20-8-6-18-28-16-4-2-14-26;/h9-12,27-30H,1-8,13-22,25-26H2;1H

Standard InChI Key:  GXISTBPWRLTNBZ-UHFFFAOYSA-N

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: 420.69

Molecular Weight (Monoisotopic): 420.3940

AlogP: 2.08

#Rotatable Bonds: 22

Polar Surface Area: 100.16

Molecular Species: BASE

HBA: 6

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 11.18

CX LogP: 1.08

CX LogD: -14.36

Aromatic Rings: 1

Heavy Atoms: 30

QED Weighted: 0.16

Np Likeness Score: -0.13

References

1. Kaur N, Delcros JG, Imran J, Khaled A, Chehtane M, Tschammer N, Martin B, Phanstiel O..  (2008)  A comparison of chloroambucil- and xylene-containing polyamines leads to improved ligands for accessing the polyamine transport system.,  51  (5): [PMID:18281932] [10.1021/jm070794t]

2. Liao CP, Phanstiel O, Lasbury ME, Zhang C, Shao S, Durant PJ, Cheng BH, Lee CH..  (2009)  Polyamine transport as a target for treatment of Pneumocystis pneumonia.,  53  (12): [PMID:19805570] [10.1128/aac.00662-09]

3. Muth A, Kamel J, Kaur N, Shicora AC, Ayene IS, Gilmour SK, Phanstiel O..  (2013)  Development of polyamine transport ligands with improved metabolic stability and selectivity against specific human cancers.,  56  (14): [PMID:23841465] [10.1021/jm400496a]

4. Muth A, Madan M, Archer JJ, Ocampo N, Rodriguez L, Phanstiel O..  (2014)  Polyamine transport inhibitors: design, synthesis, and combination therapies with difluoromethylornithine.,  57  (2): [PMID:24405276] [10.1021/jm401174a]

Source

Source(1):

• Scientific Literature