5,8-Dihydroxy-2-methyl-[1,4]naphthoquinone

ID: ALA11475

Chembl Id: CHEMBL11475

Cas Number: 14554-09-7

PubChem CID: 271296

Max Phase: Preclinical

Molecular Formula: C11H8O4

Molecular Weight: 204.18

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1=CC(=O)c2c(O)ccc(O)c2C1=O

Standard InChI:  InChI=1S/C11H8O4/c1-5-4-8(14)9-6(12)2-3-7(13)10(9)11(5)15/h2-4,12-13H,1H3

Standard InChI Key:  YKPXIWHBRBFRQM-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA11475

   Methylnaphthazarin

Molecule Features

Natural Product: Yes

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: 204.18

Molecular Weight (Monoisotopic): 204.0423

AlogP: 1.42

#Rotatable Bonds: ┄

Polar Surface Area: 74.60

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.53

CX Basic pKa: ┄

CX LogP: 2.58

CX LogD: 2.55

Aromatic Rings: 1

Heavy Atoms: 15

QED Weighted: 0.63

Np Likeness Score: 1.83

References

1. Tandon VK, Chhor RB, Singh RV, Rai S, Yadav DB..  (2004)  Design, synthesis and evaluation of novel 1,4-naphthoquinone derivatives as antifungal and anticancer agents.,  14  (5): [PMID:14980639] [10.1016/j.bmcl.2004.01.002]

2. Cui XR, Tsukada M, Suzuki N, Shimamura T, Gao L, Koyanagi J, Komada F, Saito S..  (2008)  Comparison of the cytotoxic activities of naturally occurring hydroxyanthraquinones and hydroxynaphthoquinones.,  43  (6): [PMID:17949858] [10.1016/j.ejmech.2007.08.009]

3. PubChem BioAssay data set, 

4. Zhang J, Liu Y, Shi D, Hu G, Zhang B, Li X, Liu R, Han X, Yao X, Fang J..  (2017)  Synthesis of naphthazarin derivatives and identification of novel thioredoxin reductase inhibitor as potential anticancer agent.,  140  [PMID:28987605] [10.1016/j.ejmech.2017.09.027]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays