ID: ALA1256965

Max Phase: Preclinical

Molecular Formula: C12H18Cl2N3O5P

Molecular Weight: 386.17

Molecule Type: Small molecule

Representations

Canonical SMILES:  COc1cc([N+](=O)[O-])ccc1COP(N)(=O)N(CCCl)CCCl

Standard InChI:  InChI=1S/C12H18Cl2N3O5P/c1-21-12-8-11(17(18)19)3-2-10(12)9-22-23(15,20)16(6-4-13)7-5-14/h2-3,8H,4-7,9H2,1H3,(H2,15,20)

Standard InChI Key:  LWMMVLISLWMIJU-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: 386.17

Molecular Weight (Monoisotopic): 385.0361

AlogP: 2.97

#Rotatable Bonds: 10

Polar Surface Area: 107.93

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa:

CX LogP: 1.49

CX LogD: 1.49

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.29

Np Likeness Score: -0.57

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