4-((4-Iodophenyl)amino)-2,2-dimethyl-3,4-dihydro-2Hbenzo[g]chromene-5,10-dione

ID: ALA3114587

PubChem CID: 76321465

Max Phase: Preclinical

Molecular Formula: C21H18INO3

Molecular Weight: 459.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)CC(Nc2ccc(I)cc2)C2=C(O1)C(=O)c1ccccc1C2=O

Standard InChI:  InChI=1S/C21H18INO3/c1-21(2)11-16(23-13-9-7-12(22)8-10-13)17-18(24)14-5-3-4-6-15(14)19(25)20(17)26-21/h3-10,16,23H,11H2,1-2H3

Standard InChI Key:  BYEGKHWKKSCKSO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   28.1244  -13.7949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9486  -13.7947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5363  -13.0811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8277  -13.8063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8265  -14.6327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5406  -15.0452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5388  -13.3939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2534  -13.8026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2568  -14.6348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9752  -15.0457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9684  -13.3813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9639  -12.5571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.9775  -15.8698    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.6914  -13.7967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6925  -14.6260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4072  -15.0374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1255  -14.6242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4051  -13.3789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.4071  -15.8616    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.1208  -16.2736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1175  -17.0956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8304  -17.5076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5451  -17.0956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5425  -16.2672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8291  -15.8589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2610  -17.5101    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  1  3  1  0
  4  5  2  0
  5  6  1  0
  6  9  2  0
  8  7  2  0
  7  4  1  0
  8  9  1  0
  8 11  1  0
  9 10  1  0
 10 15  1  0
 14 11  1  0
 11 12  2  0
 10 13  2  0
 14 15  2  0
 14 18  1  0
 15 16  1  0
 16 17  1  0
 17  1  1  0
  1 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 23 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3114587

   4-(4-Iodoanilino)-2,2-dimethyl-3,4-dihydrobenzo[g]chromene-5,10-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: 459.28

Molecular Weight (Monoisotopic): 459.0331

AlogP: 4.60

#Rotatable Bonds: 2

Polar Surface Area: 55.40

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.86

CX LogP: 3.74

CX LogD: 3.74

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.67

Np Likeness Score: 0.13

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