2-(3-(4-chlorobenzyloxy)-2-methylbenzoyl)-3-hydroxycyclohex-2-en-1-one

ID: ALA4529209

PubChem CID: 155545383

Max Phase: Preclinical

Molecular Formula: C21H19ClO4

Molecular Weight: 370.83

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1c(OCc2ccc(Cl)cc2)cccc1C(=O)C1=C(O)CCCC1=O

Standard InChI:  InChI=1S/C21H19ClO4/c1-13-16(21(25)20-17(23)5-3-6-18(20)24)4-2-7-19(13)26-12-14-8-10-15(22)11-9-14/h2,4,7-11,23H,3,5-6,12H2,1H3

Standard InChI Key:  APBWDJFEONSPAH-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   10.8835  -21.0447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7216  -20.2399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7205  -21.0594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4285  -21.4684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1382  -21.0590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1353  -20.2363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4267  -19.8310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0138  -19.8315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0136  -19.0143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3062  -20.2402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5965  -19.8247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8910  -20.2300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5947  -21.4582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3063  -21.0512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5999  -19.0076    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0132  -21.4613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8415  -19.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5508  -20.2310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2569  -19.8197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9646  -20.2290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6703  -19.8184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6676  -19.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9534  -18.5946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2507  -19.0076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3732  -18.5882    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   14.4243  -19.0138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  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
  2  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 10 14  1  0
 11 12  1  0
 12  1  1  0
  1 13  1  0
 13 14  1  0
 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
 22 25  1  0
  7 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4529209

   ---

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: 370.83

Molecular Weight (Monoisotopic): 370.0972

AlogP: 4.98

#Rotatable Bonds: 5

Polar Surface Area: 63.60

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.59

CX Basic pKa: ┄

CX LogP: 4.69

CX LogD: 1.95

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.60

Np Likeness Score: -0.22

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