2,5-Dihydroxy-1,4-naphthalenedione

ID: ALA1576702

Max Phase: Preclinical

Molecular Formula: C10H6O4

Molecular Weight: 190.15

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1C=C(O)c2c(O)cccc2C1=O

Standard InChI:  InChI=1S/C10H6O4/c11-6-3-1-2-5-9(6)7(12)4-8(13)10(5)14/h1-4,11-12H

Standard InChI Key:  AQMHLTLDUPBBEF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 14 15  0  0  0  0  0  0  0  0999 V2000
   -0.7061    1.7619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7061   -1.5381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1351    0.9369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7228   -1.5381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0083   -0.3006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0083    0.5244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7061    0.9369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7061   -0.7131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4206    0.5244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7228   -0.7131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4206   -0.3006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7228    0.9369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4373   -0.3006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4373    0.5244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  2  0
  2  8  1  0
  3  9  2  0
  4 10  1  0
  5  6  1  0
  5  8  1  0
  5 10  2  0
  6  7  1  0
  6 12  2  0
  7  9  1  0
  8 11  2  0
  9 11  1  0
 10 13  1  0
 12 14  1  0
 13 14  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1576702

   ---

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: 190.15

Molecular Weight (Monoisotopic): 190.0266

AlogP: 1.06

#Rotatable Bonds: ┄

Polar Surface Area: 74.60

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.89

CX Basic pKa: ┄

CX LogP: 1.15

CX LogD: -1.20

Aromatic Rings: 1

Heavy Atoms: 14

QED Weighted: 0.60

Np Likeness Score: 1.47

References

1. Bonifazi EL, Ríos-Luci C, León LG, Burton G, Padrón JM, Misico RI..  (2010)  Antiproliferative activity of synthetic naphthoquinones related to lapachol. First synthesis of 5-hydroxylapachol.,  18  (7): [PMID:20304655] [10.1016/j.bmc.2010.02.032]

2. PubChem BioAssay data set, 

3. Pelageev DN, Dyshlovoy SA, Pokhilo ND, Denisenko VA, Borisova KL, Keller-von Amsberg G, Bokemeyer C, Fedorov SN, Honecker F, Anufriev VP..  (2014)  Quinone-carbohydrate nonglucoside conjugates as a new type of cytotoxic agents: synthesis and determination of in vitro activity.,  77  [PMID:24631733] [10.1016/j.ejmech.2014.03.006]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays