SID87335718

ID: ALA1723955

Chembl Id: CHEMBL1723955

Cas Number: 6307-22-8

PubChem CID: 237490

Max Phase: Preclinical

Molecular Formula: C18H14ClNO2

Molecular Weight: 311.77

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1C(Cl)=C(NCCc2ccccc2)C(=O)c2ccccc21

Standard InChI:  InChI=1S/C18H14ClNO2/c19-15-16(20-11-10-12-6-2-1-3-7-12)18(22)14-9-5-4-8-13(14)17(15)21/h1-9,20H,10-11H2

Standard InChI Key:  PNCKVMGGVODNEF-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA1723955

   2-Chloro-3-(phenethylamino)naphthalene-1,4-dione

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: 311.77

Molecular Weight (Monoisotopic): 311.0713

AlogP: 3.35

#Rotatable Bonds: 4

Polar Surface Area: 46.17

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.17

CX LogD: 3.17

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.94

Np Likeness Score: -0.24

References

1. PubChem BioAssay data set, 

2. Prachayasittikul V, Pingaew R, Worachartcheewan A, Nantasenamat C, Prachayasittikul S, Ruchirawat S, Prachayasittikul V..  (2014)  Synthesis, anticancer activity and QSAR study of 1,4-naphthoquinone derivatives.,  84  [PMID:25019480] [10.1016/j.ejmech.2014.07.024]

3. Tomek P, Palmer BD, Flanagan JU, Sun C, Raven EL, Ching LM..  (2017)  Discovery and evaluation of inhibitors to the immunosuppressive enzyme indoleamine 2,3-dioxygenase 1 (IDO1): Probing the active site-inhibitor interactions.,  126  [PMID:28011425] [10.1016/j.ejmech.2016.12.029]

4. Dallaston MA, Rajan S, Chekaiban J, Wibowo M, Cross M, Coster MJ, Davis RA, Hofmann A..  (2017)  Dichloro-naphthoquinone as a non-classical inhibitor of the mycobacterial carbonic anhydrase Rv3588c.,  8  (6): [PMID:30108843] [10.1039/C7MD00090A]

5. Johannes Zuegg, Alysha Elliott, Maite Amado, Emma Cowie, Ali Hinton, Geraldine Kaeslin, Angela Kavanagh, Anne Kunert, Gabriell Lowe, Soumya Ramu, Janet Reid, Robin Trauer, Mathilde Desselle, Ruth Neale, Karl Hansford, Mark Blascovich, Matthew Cooper. CO-ADD screening of NIH NCI Diversity Set V,  [10.6019/CHEMBL4296182]

6. Varricchio C,Beirne K,Aeschlimann P,Heard C,Rozanowska M,Votruba M,Brancale A.  (2020)  Discovery of Novel 2-Aniline-1,4-naphthoquinones as Potential New Drug Treatment for Leber's Hereditary Optic Neuropathy (LHON).,  63  (22): [PMID:33180495] [10.1021/acs.jmedchem.0c00942]

Source

Source(3):

• Scientific Literature
• PubChem BioAssays
• CO-ADD antimicrobial screening data