rac-(R*,R*)-2-Amino-3-hydroxy-1-(4-[(4-([4-(hydroxymethyl)phenyl]ethynyl)phenyl)methyl]piperidin-1-yl)-4-(methanesulfonyl)butan-1-one

ID: ALA4756867

PubChem CID: 155289365

Max Phase: Preclinical

Molecular Formula: C26H32N2O5S

Molecular Weight: 484.62

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CS(=O)(=O)C[C@H](O)[C@@H](N)C(=O)N1CCC(Cc2ccc(C#Cc3ccc(CO)cc3)cc2)CC1

Standard InChI:  InChI=1S/C26H32N2O5S/c1-34(32,33)18-24(30)25(27)26(31)28-14-12-22(13-15-28)16-21-8-4-19(5-9-21)2-3-20-6-10-23(17-29)11-7-20/h4-11,22,24-25,29-30H,12-18,27H2,1H3/t24-,25+/m0/s1

Standard InChI Key:  RNBZGRMVKCFVJP-LOSJGSFVSA-N

Molfile:  

 
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   24.3453  -17.7621    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   24.7578  -18.4766    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   16.4915  -13.2171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7764  -13.6302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7797  -14.4595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4943  -14.8676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   24.3471  -16.9409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6347  -18.1795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
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 24 25  1  0
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 27 28  2  0
 28 29  1  0
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 28 31  1  0
 31 32  1  0
  9 33  1  1
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  2 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4756867

   ---

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: 484.62

Molecular Weight (Monoisotopic): 484.2032

AlogP: 1.09

#Rotatable Bonds: 7

Polar Surface Area: 120.93

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.53

CX Basic pKa: 7.07

CX LogP: 0.82

CX LogD: 0.66

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.51

Np Likeness Score: -0.39

References

1. Yamada Y,Takashima H,Walmsley DL,Ushiyama F,Matsuda Y,Kanazawa H,Yamaguchi-Sasaki T,Tanaka-Yamamoto N,Yamagishi J,Kurimoto-Tsuruta R,Ogata Y,Ohtake N,Angove H,Baker L,Harris R,Macias A,Robertson A,Surgenor A,Watanabe H,Nakano K,Mima M,Iwamoto K,Okada A,Takata I,Hitaka K,Tanaka A,Fujita K,Sugiyama H,Hubbard RE.  (2020)  Fragment-Based Discovery of Novel Non-Hydroxamate LpxC Inhibitors with Antibacterial Activity.,  63  (23): [PMID:33210531] [10.1021/acs.jmedchem.0c01215]

2. de Esch IJP, Erlanson DA, Jahnke W, Johnson CN, Walsh L..  (2022)  Fragment-to-Lead Medicinal Chemistry Publications in 2020.,  65  (1.0): [PMID:34928151] [10.1021/acs.jmedchem.1c01803]

Source

Source(1):

• Scientific Literature