(R)-2-((R)-3-Amino-3-(4-((2-isopropoxyquinolin-4-yl)methoxy)phenyl)-2-oxopyrrolidin-1-yl)-N-hydroxy-4-methylpentanamide

ID: ALA3221859

PubChem CID: 90668116

Max Phase: Preclinical

Molecular Formula: C29H36N4O4

Molecular Weight: 504.63

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)C[C@H](C(=O)NO)N1CC[C@@](N)(c2ccc(OCc3cc(C(C)C)nc4ccccc34)cc2)C1=O

Standard InChI:  InChI=1S/C29H36N4O4/c1-18(2)15-26(27(34)32-36)33-14-13-29(30,28(33)35)21-9-11-22(12-10-21)37-17-20-16-25(19(3)4)31-24-8-6-5-7-23(20)24/h5-12,16,18-19,26,36H,13-15,17,30H2,1-4H3,(H,32,34)/t26-,29-/m1/s1

Standard InChI Key:  BEAXBRZKAOFZEU-GGXMVOPNSA-N

Molfile:  

     RDKit          2D

 37 40  0  0  0  0  0  0  0  0999 V2000
    7.6453   -5.3551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2380   -6.0720    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.9820   -6.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4739   -7.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6889   -6.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9820   -4.8164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4499   -5.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2221   -8.4013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2210   -6.9543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6889   -4.8164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6285   -6.2417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.6376   -7.6797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3979   -5.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4194   -6.1573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3505   -8.3606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9238   -5.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3979   -6.9543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2210   -5.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6483   -7.5767    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5122   -6.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3979   -4.1038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6285   -4.8164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5122   -4.8164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3094   -4.6059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2731   -5.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7513   -5.5292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1588   -6.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7861   -6.6834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2952   -7.0587    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1207   -6.9279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5395   -6.3519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2210   -4.1038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4439   -4.6887    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9116   -5.4927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0822   -5.6002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5744   -4.9357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7605   -6.3722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0
  2  1  1  0
 22 18  2  0
  9 17  1  0
  2 28  1  0
 20  5  1  0
 10 23  2  0
 12  4  1  0
 27  3  1  0
 30 19  1  0
  9 12  1  0
 26 27  1  0
 19 15  1  0
 17  3  2  0
 13 18  1  0
 25 10  1  0
 11 18  1  0
 30 14  1  0
  7 31  1  0
  6 21  1  0
  7 25  1  0
  3 13  1  0
  2 14  1  0
 23 16  1  0
 32 22  1  0
 21 32  2  0
 11  9  2  0
 16 26  1  0
 12  8  1  0
 16 20  2  0
 25  5  2  0
  1 24  2  0
 31 28  1  0
 13  6  2  0
 30 29  2  0
  7 33  1  1
 14 34  1  1
 34 35  1  0
 35 36  1  0
 35 37  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3221859

   (2R)-2-[(3R)-3-amino-2-oxo-3-[4-[(2-propan-2-ylquinolin-4-yl)methoxy]phenyl]pyrrolidin-1-yl]-N-hydroxy-4-methylpentanamide

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: 504.63

Molecular Weight (Monoisotopic): 504.2737

AlogP: 4.24

#Rotatable Bonds: 9

Polar Surface Area: 117.78

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.74

CX Basic pKa: 7.46

CX LogP: 3.80

CX LogD: 3.62

Aromatic Rings: 3

Heavy Atoms: 37

QED Weighted: 0.30

Np Likeness Score: -0.40

References

1. Argade A, Bahekar R, Desai J, Thombare P, Shah K, Gite S, Sunder R, Ranvir R, Bandyopadhyay D, Chakrabarti G, Joharapurkar A, Mahapatra J, Chatterjee A, Patel H, Shaikh M, Sairam KVVM, Jain M, Patel P.  (2011)  Design, synthesis and biological evaluation of -lactam hydroxamate based TACE inhibitors,  2  (10): [10.1039/C0MD00261E]

Source

Source(1):

• Scientific Literature