ID: ALA1256989

Max Phase: Preclinical

Molecular Formula: C12H18Cl2N3O4P

Molecular Weight: 370.17

Molecule Type: Small molecule

Representations

Canonical SMILES:  Cc1cc(COP(N)(=O)N(CCCl)CCCl)ccc1[N+](=O)[O-]

Standard InChI:  InChI=1S/C12H18Cl2N3O4P/c1-10-8-11(2-3-12(10)17(18)19)9-21-22(15,20)16(6-4-13)7-5-14/h2-3,8H,4-7,9H2,1H3,(H2,15,20)

Standard InChI Key:  YVZXKRFANTWCEF-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

Properties

Molecular Weight: 370.17

Molecular Weight (Monoisotopic): 369.0412

AlogP: 3.27

#Rotatable Bonds: 9

Polar Surface Area: 98.70

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa:

CX LogP: 2.16

CX LogD: 2.16

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.31

Np Likeness Score: -0.79

References

1. Hall BS, Wu X, Hu L, Wilkinson SR..  (2010)  Exploiting the drug-activating properties of a novel trypanosomal nitroreductase.,  54  (3): [PMID:20028822] [10.1128/aac.01213-09]

2. Hu L, Wu X, Han J, Chen L, Vass SO, Browne P, Hall BS, Bot C, Gobalakrishnapillai V, Searle PF, Knox RJ, Wilkinson SR..  (2011)  Synthesis and structure-activity relationships of nitrobenzyl phosphoramide mustards as nitroreductase-activated prodrugs.,  21  (13): [PMID:21620697] [10.1016/j.bmcl.2011.05.009]

3. Nepali K, Lee HY, Liou JP..  (2019)  Nitro-Group-Containing Drugs.,  62  (6): [PMID:30295477] [10.1021/acs.jmedchem.8b00147]

Source

Source(1):

• Scientific Literature