2-Bromo-3-methyl-[1,4]naphthoquinone

ID: ALA181549

Chembl Id: CHEMBL181549

Cas Number: 3129-39-3

PubChem CID: 123179

Max Phase: Preclinical

Molecular Formula: C11H7BrO2

Molecular Weight: 251.08

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1=C(Br)C(=O)c2ccccc2C1=O

Standard InChI:  InChI=1S/C11H7BrO2/c1-6-9(12)11(14)8-5-3-2-4-7(8)10(6)13/h2-5H,1H3

Standard InChI Key:  AVHXUWPFOZVLBX-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA181549

   2-Bromo-3-methylnaphthoquinone

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: 251.08

Molecular Weight (Monoisotopic): 249.9629

AlogP: 2.73

#Rotatable Bonds: ┄

Polar Surface Area: 34.14

Molecular Species: ┄

HBA: 2

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.44

CX LogD: 2.44

Aromatic Rings: 1

Heavy Atoms: 14

QED Weighted: 0.71

Np Likeness Score: 0.55

References

1. Jung YS, Joe BY, Cho SJ, Konishi Y..  (2005)  2,3-Dimethoxy-5-methyl-1,4-benzoquinones and 2-methyl-1,4-naphthoquinones: glycation inhibitors with lipid peroxidation activity.,  15  (4): [PMID:15686926] [10.1016/j.bmcl.2004.12.029]

2. Kayashima T, Mori M, Mizutani R, Nishio K, Kuramochi K, Tsubaki K, Yoshida H, Mizushina Y, Matsubara K..  (2010)  Synthesis and biological evaluation of vitamin K derivatives as angiogenesis inhibitor.,  18  (17): [PMID:20688522] [10.1016/j.bmc.2010.07.022]

3. Nasiri HR, Madej MG, Panisch R, Lafontaine M, Bats JW, Lancaster CR, Schwalbe H..  (2013)  Design, synthesis, and biological testing of novel naphthoquinones as substrate-based inhibitors of the quinol/fumarate reductase from Wolinella succinogenes.,  56  (23): [PMID:24251984] [10.1021/jm400978u]

4. Vermeer C, van 't Hoofd C, Knapen MHJ, Xanthoulea S..  (2017)  Synthesis of 2-methyl-1,4-naphthoquinones with higher gamma-glutamyl carboxylase activity than MK-4 both in vitro and in vivo.,  27  (2): [PMID:27955810] [10.1016/j.bmcl.2016.11.073]

5. Furqan M, Fayyaz A, Firdous F, Raza H, Bilal A, Saleem RSZ, Shahzad-Ul-Hussan S, Wang D, Youssef FS, Al Musayeib NM, Ashour ML, Hussain H, Faisal A..  (2022)  Identification and Characterization of Natural and Semisynthetic Quinones as Aurora Kinase Inhibitors.,  85  (6.0): [PMID:35687347] [10.1021/acs.jnatprod.1c01222]

Source

Source(1):

• Scientific Literature