2-Amino-2-[(4-([3-((2-[(1S)-1-hydroxyethyl]-1H-imidazol-1-yl)methyl)-1,2-oxazol-5-yl]ethynyl)phenoxy)methyl]propane-1,3-diol

ID: ALA4747965

PubChem CID: 150045929

Max Phase: Preclinical

Molecular Formula: C21H24N4O5

Molecular Weight: 412.45

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C[C@H](O)c1nccn1Cc1cc(C#Cc2ccc(OCC(N)(CO)CO)cc2)on1

Standard InChI:  InChI=1S/C21H24N4O5/c1-15(28)20-23-8-9-25(20)11-17-10-19(30-24-17)7-4-16-2-5-18(6-3-16)29-14-21(22,12-26)13-27/h2-3,5-6,8-10,15,26-28H,11-14,22H2,1H3/t15-/m0/s1

Standard InChI Key:  DKGUWMFQYQOPSO-HNNXBMFYSA-N

Molfile:  

 
     RDKit          2D

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    7.7674  -15.7124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0218  -14.9357    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3588  -14.4536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7001  -14.9357    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3576  -13.6364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0647  -13.2267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6492  -13.2288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9228  -14.6835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3157  -15.2306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5204  -15.0632    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1121  -15.7711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6592  -16.3781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4055  -16.0453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4898  -17.1776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3203  -17.9777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1509  -18.7771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3750  -19.0261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2055  -19.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8136  -20.3720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5937  -20.1151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7596  -19.3171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6452  -21.1717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8686  -21.4257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2601  -20.8802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4285  -20.0805    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4835  -21.1342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8751  -20.5887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0907  -21.6785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6982  -22.2251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  1  1  0
  4  6  1  0
  6  7  1  6
  6  8  1  0
  5  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 10  1  0
 13 15  1  0
 15 16  3  0
 16 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
 24 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 25 29  1  0
 29 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4747965

   ---

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: 412.45

Molecular Weight (Monoisotopic): 412.1747

AlogP: 0.43

#Rotatable Bonds: 8

Polar Surface Area: 139.79

Molecular Species: BASE

HBA: 9

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.70

CX Basic pKa: 8.68

CX LogP: -0.19

CX LogD: -1.48

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.39

Np Likeness Score: -0.88

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