3-hydroxy-2-(3-(4-isopropylbenzyloxy)-2-nitrobenzoyl)cyclohex-2-en-1-one

ID: ALA4571726

PubChem CID: 155562740

Max Phase: Preclinical

Molecular Formula: C23H23NO6

Molecular Weight: 409.44

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)c1ccc(COc2cccc(C(=O)C3=C(O)CCCC3=O)c2[N+](=O)[O-])cc1

Standard InChI:  InChI=1S/C23H23NO6/c1-14(2)16-11-9-15(10-12-16)13-30-20-8-3-5-17(22(20)24(28)29)23(27)21-18(25)6-4-7-19(21)26/h3,5,8-12,14,25H,4,6-7,13H2,1-2H3

Standard InChI Key:  FROQYABGSNELPQ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   32.3230   -3.7227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3219   -4.5423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0299   -4.9512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7396   -4.5418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7368   -3.7191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0281   -3.3139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6152   -3.3143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6150   -2.4971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.9076   -3.7231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   30.1961   -4.9410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9078   -4.5341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2013   -2.4904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.6146   -4.9441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.4429   -3.3079    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.1522   -3.7138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8583   -3.3025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5660   -3.7119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2717   -3.3013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2690   -2.4832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5548   -2.0775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8521   -2.4904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0257   -2.4967    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.9747   -2.0710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7322   -2.0860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.3168   -2.0902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.6844   -2.4760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9705   -1.2538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
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  6  7  2  0
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  1 13  1  0
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 11 15  1  0
 14 16  2  0
  6 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
  7 25  1  0
 22 26  1  0
 25 27  1  0
 25 28  2  0
 26 29  1  0
 26 30  1  0
M  CHG  2  25   1  27  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4571726

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 409.44

Molecular Weight (Monoisotopic): 409.1525

AlogP: 5.05

#Rotatable Bonds: 7

Polar Surface Area: 106.74

Molecular Species: ACID

HBA: 6

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.02

CX Basic pKa: ┄

CX LogP: 4.75

CX LogD: 1.61

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.30

Np Likeness Score: -0.26

References

1. Ndikuryayo F, Kang WM, Wu FX, Yang WC, Yang GF..  (2019)  Hydrophobicity-oriented drug design (HODD) of new human 4-hydroxyphenylpyruvate dioxygenase inhibitors.,  166  [PMID:30684868] [10.1016/j.ejmech.2019.01.032]

Source

Source(1):

• Scientific Literature