2,2-Dimethyl-3-(phenylthio)-2,3-dihydronaphtho[2,3-b]furan-4,9-dione

ID: ALA3114423

PubChem CID: 76321451

Max Phase: Preclinical

Molecular Formula: C20H16O3S

Molecular Weight: 336.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)OC2=C(C(=O)c3ccccc3C2=O)C1Sc1ccccc1

Standard InChI:  InChI=1S/C20H16O3S/c1-20(2)19(24-12-8-4-3-5-9-12)15-16(21)13-10-6-7-11-14(13)17(22)18(15)23-20/h3-11,19H,1-2H3

Standard InChI Key:  CSKHKZLUBWGDKA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
   18.4561  -27.3882    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   19.2345  -27.6586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3852  -28.4661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1622  -28.7371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7867  -28.1986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6290  -27.3859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8521  -27.1187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2041  -26.6040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6955  -25.9333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4077  -26.3470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4098  -25.5233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5501  -25.5255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5490  -26.3516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2626  -26.7638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2608  -25.1135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9752  -25.5219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9785  -26.3537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6965  -26.7643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6897  -25.1008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6852  -24.2772    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6987  -27.5880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4156  -25.5128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4135  -26.3449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2075  -25.2578    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  2  1  0
 10  9  1  0
  9 11  1  0
 12 13  2  0
 13 14  1  0
 14 17  2  0
 16 15  2  0
 15 12  1  0
 16 17  1  0
 16 19  1  0
 17 18  1  0
 18 23  1  0
 22 19  1  0
 19 20  2  0
 18 21  2  0
 22 23  2  0
 23  8  1  0
  8  9  1  0
  9 24  1  0
 24 22  1  0
  8  1  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3114423

   2,2-dimethyl-3-phenylsulfanyl-3H-benzo[f][1]benzofuran-4,9-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: 336.41

Molecular Weight (Monoisotopic): 336.0820

AlogP: 4.29

#Rotatable Bonds: 2

Polar Surface Area: 43.37

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.62

CX LogD: 3.62

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.82

Np Likeness Score: 0.53

References

1. da Cruz EH, Hussene CM, Dias GG, Diogo EB, de Melo IM, Rodrigues BL, da Silva MG, Valença WO, Camara CA, de Oliveira RN, de Paiva YG, Goulart MO, Cavalcanti BC, Pessoa C, da Silva Júnior EN..  (2014)  1,2,3-triazole-, arylamino- and thio-substituted 1,4-naphthoquinones: potent antitumor activity, electrochemical aspects, and bioisosteric replacement of C-ring-modified lapachones.,  22  (5): [PMID:24530030] [10.1016/j.bmc.2014.01.033]

Source

Source(1):

• Scientific Literature