N-hydroxy-2(R)-[[(R)-methylphenylphosphinyl]-benzylamino]-4-methylpentanamide

ID: ALA176602

PubChem CID: 9543420

Max Phase: Preclinical

Molecular Formula: C20H27N2O3P

Molecular Weight: 374.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)C[C@H](C(=O)NO)N(Cc1ccccc1)[P@](C)(=O)c1ccccc1

Standard InChI:  InChI=1S/C20H27N2O3P/c1-16(2)14-19(20(23)21-24)22(15-17-10-6-4-7-11-17)26(3,25)18-12-8-5-9-13-18/h4-13,16,19,24H,14-15H2,1-3H3,(H,21,23)/t19-,26-/m1/s1

Standard InChI Key:  KGUVBHLPMGERAT-NIYFSFCBSA-N

Molfile:  

     RDKit          2D

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    0.3708   -2.1885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3708   -3.0135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3437   -3.4260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0581   -3.0135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0581   -2.1885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3437   -0.9510    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    0.4813   -0.9510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1687   -0.9510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3437   -0.1260    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0581    0.2865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0581    1.1115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7726    1.5240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7726    2.3490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.3437    2.3490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3437    1.5240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3708    0.2865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0853   -0.1260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7997    0.2865    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5142   -0.1260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0853   -0.9510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3708    1.1115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0853    1.5240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0853    2.3490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7997    1.1115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  1  6  1  0
  1  7  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  8  7  2  0
  7  9  1  1
  7 10  1  6
 11 10  1  0
 18 10  1  6
 11 12  1  0
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 13 14  1  0
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 15 16  1  0
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 18 23  1  0
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 19 22  2  0
 20 21  1  0
 23 24  1  0
 25 24  1  0
 26 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA176602

   n-[[2-Methyl-4-hydroxycarbamoyl]but-4-yl-n]-benzyl-p-[phenyl]-p-[methyl]phosphinamid

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: 374.42

Molecular Weight (Monoisotopic): 374.1759

AlogP: 3.64

#Rotatable Bonds: 8

Polar Surface Area: 69.64

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.72

CX Basic pKa: 1.94

CX LogP: 3.04

CX LogD: 3.02

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.42

Np Likeness Score: -0.23

References

1. Pikul S, McDow Dunham KL, Almstead NG, De B, Natchus MG, Anastasio MV, McPhail SJ, Snider CE, Taiwo YO, Chen L, Dunaway CM, Gu F, Mieling GE..  (1999)  Design and synthesis of phosphinamide-based hydroxamic acids as inhibitors of matrix metalloproteinases.,  42  (1): [PMID:9888835] [10.1021/jm980142s]

Source

Source(1):

• Scientific Literature