rac-4'-(1-((4-(hydroxycarbamoyl)phenyl)carbamoyl)cyclopentyl)-[1,1'-biphenyl]-3-carboxylic acid

ID: ALA4640415

PubChem CID: 156015592

Max Phase: Preclinical

Molecular Formula: C26H24N2O5

Molecular Weight: 444.49

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(O)c1cccc(-c2ccc(C3(C(=O)Nc4ccc(C(=O)NO)cc4)CCCC3)cc2)c1

Standard InChI:  InChI=1S/C26H24N2O5/c29-23(28-33)18-8-12-22(13-9-18)27-25(32)26(14-1-2-15-26)21-10-6-17(7-11-21)19-4-3-5-20(16-19)24(30)31/h3-13,16,33H,1-2,14-15H2,(H,27,32)(H,28,29)(H,30,31)

Standard InChI Key:  LXUDZYCOGQLEHS-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
    6.3375  -30.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1625  -30.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4192  -29.4325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7500  -28.9458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0849  -29.4325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6069  -27.7082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6058  -28.5356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3206  -28.9485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0370  -28.5351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0341  -27.7046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3187  -27.2955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4660  -28.5329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1810  -28.9443    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8949  -28.5307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6086  -28.9434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3220  -28.5305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3212  -27.7046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6011  -27.2934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8906  -27.7086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0344  -27.2901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7501  -27.7004    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.4633  -27.2858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4646  -27.7079    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0320  -26.4650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8945  -27.2961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8956  -26.4700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1818  -26.0577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4664  -26.4705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4694  -27.2997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1836  -27.7082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7564  -27.7149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0404  -27.3051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7596  -28.5399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  1  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
  9  4  1  0
  4 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 17 20  1  0
 20 21  1  0
 21 22  1  0
 12 23  2  0
 20 24  2  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 25  1  0
  6 25  1  0
 29 31  1  0
 31 32  1  0
 31 33  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4640415

   ---

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: 444.49

Molecular Weight (Monoisotopic): 444.1685

AlogP: 4.62

#Rotatable Bonds: 6

Polar Surface Area: 115.73

Molecular Species: ACID

HBA: 4

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.00

CX Basic pKa: ┄

CX LogP: 4.72

CX LogD: 1.56

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.33

Np Likeness Score: -0.82

References

1. Tng J, Lim J, Wu KC, Lucke AJ, Xu W, Reid RC, Fairlie DP..  (2020)  Achiral Derivatives of Hydroxamate AR-42 Potently Inhibit Class I HDAC Enzymes and Cancer Cell Proliferation.,  63  (11): [PMID:32383881] [10.1021/acs.jmedchem.0c00230]

Source

Source(1):

• Scientific Literature