4-(9,10-dioxo-9,10-dihydroanthracen-1-yl)benzoic acid

ID: ALA4582525

PubChem CID: 139199281

Max Phase: Preclinical

Molecular Formula: C21H12O4

Molecular Weight: 328.32

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(O)c1ccc(-c2cccc3c2C(=O)c2ccccc2C3=O)cc1

Standard InChI:  InChI=1S/C21H12O4/c22-19-15-4-1-2-5-16(15)20(23)18-14(6-3-7-17(18)19)12-8-10-13(11-9-12)21(24)25/h1-11H,(H,24,25)

Standard InChI Key:  MNROZOOVFISMNF-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
   12.9086   -5.7574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9074   -6.5770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6155   -6.9859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6137   -5.3486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3223   -5.7538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3211   -6.5745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0273   -6.9835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0296   -5.3423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7404   -5.7558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7387   -6.5729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4443   -6.9810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1520   -6.5733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1498   -5.7532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4436   -5.3487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0297   -4.5251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0267   -7.8007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4417   -4.5315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1467   -4.1240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1451   -3.3076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4359   -2.8998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7269   -3.3145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7319   -4.1296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4329   -2.0826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1391   -1.6715    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7237   -1.6767    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  5  8  1  0
  6  7  1  0
  7 10  1  0
  9  8  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
  8 15  2  0
  7 16  2  0
 14 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
 20 23  1  0
 23 24  1  0
 23 25  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4582525

   ---

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: 328.32

Molecular Weight (Monoisotopic): 328.0736

AlogP: 3.83

#Rotatable Bonds: 2

Polar Surface Area: 71.44

Molecular Species: ACID

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.03

CX Basic pKa: ┄

CX LogP: 4.22

CX LogD: 1.08

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.61

Np Likeness Score: 0.26

References

1. Lee D, Pagire HS, Pagire SH, Bae EJ, Dighe M, Kim M, Lee KM, Jang YK, Jaladi AK, Jung KY, Yoo EK, Gim HE, Lee S, Choi WI, Chi YI, Song JS, Bae MA, Jeon YH, Lee GH, Liu KH, Lee T, Park S, Jeon JH, Lee IK, Ahn JH..  (2019)  Discovery of Novel Pyruvate Dehydrogenase Kinase 4 Inhibitors for Potential Oral Treatment of Metabolic Diseases.,  62  (2): [PMID:30623649] [10.1021/acs.jmedchem.8b01168]

Source

Source(1):

• Scientific Literature