ID: ALA62074

Max Phase: Preclinical

Molecular Formula: C13H8O3

Molecular Weight: 212.20

Molecule Type: Small molecule

Representations

Canonical SMILES:  Cc1cc2c(o1)C(=O)c1ccccc1C2=O

Standard InChI:  InChI=1S/C13H8O3/c1-7-6-10-11(14)8-4-2-3-5-9(8)12(15)13(10)16-7/h2-6H,1H3

Standard InChI Key:  XUZHFXXIFCAROU-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: 212.20

Molecular Weight (Monoisotopic): 212.0473

AlogP: 2.36

#Rotatable Bonds: 0

Polar Surface Area: 47.28

Molecular Species: NEUTRAL

HBA: 3

HBD: 0

#RO5 Violations: 0

HBA (Lipinski): 3

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa:

CX LogP: 2.18

CX LogD: 2.18

Aromatic Rings: 2

Heavy Atoms: 16

QED Weighted: 0.57

Np Likeness Score: 0.72

References

1. Hayashi T, Smith FT, Lee KH..  (1987)  Antitumor agents. 89. Psychorubrin, a new cytotoxic naphthoquinone from Psychotria rubra and its structure-activity relationships.,  30  (11): [PMID:3669007] [10.1021/jm00394a013]

2. Goulart MO, Zani CL, Tonholo J, Freitas LR, de Abreu FC, Oliveira AB, Raslan DS, Starling S, Chiari E.  (1997)  Trypanocidal activity and redox potential of heterocyclic- and 2-hydroxy-naphthoquinones,  7  (15): [10.1016/S0960-894X(97)00354-5]

3. Reichstein A, Vortherms S, Bannwitz S, Tentrop J, Prinz H, Müller K..  (2012)  Synthesis and structure-activity relationships of lapacho analogues. 1. Suppression of human keratinocyte hyperproliferation by 2-substituted naphtho[2,3-b]furan-4,9-diones, activation by enzymatic one- and two-electron reduction, and intracellular generation of superoxide.,  55  (16): [PMID:22845014] [10.1021/jm3009597]

4. Patel OPS, Beteck RM, Legoabe LJ..  (2021)  Antimalarial application of quinones: A recent update.,  210  [PMID:33333397] [10.1016/j.ejmech.2020.113084]

Source

Source(1):

• Scientific Literature