Moxalactam

ID: ALA519374

PubChem CID: 5488645

Max Phase: Preclinical

Molecular Formula: C20H20N6O9S

Molecular Weight: 520.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CO[C@@]1(NC(=O)[C@H](C(=O)O)c2ccc(O)cc2)C(=O)N2C(C(=O)O)=C(CSc3nnnn3C)CO[C@@H]21

Standard InChI:  InChI=1S/C20H20N6O9S/c1-25-19(22-23-24-25)36-8-10-7-35-18-20(34-2,17(33)26(18)13(10)16(31)32)21-14(28)12(15(29)30)9-3-5-11(27)6-4-9/h3-6,12,18,27H,7-8H2,1-2H3,(H,21,28)(H,29,30)(H,31,32)/t12-,18-,20+/m1/s1

Standard InChI Key:  JWCSIUVGFCSJCK-LIUKBUMOSA-N

Molfile:  

     RDKit          2D

 37 40  0  0  0  0  0  0  0  0999 V2000
    6.2074  -13.9088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3902  -13.0916    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2074  -13.0874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3902  -13.9088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9131  -13.4878    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8490  -12.6830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6803  -12.6706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0813  -12.9554    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8242  -11.8658    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6189  -13.8923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0318  -11.6429    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5819  -12.3115    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9745  -13.0916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6803  -14.3174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3246  -13.4713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6803  -11.8534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0304  -13.8716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5630  -13.0916    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.9745  -13.9088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7893  -12.5096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2688  -12.6788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3122  -12.6541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6118  -14.6021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6312  -14.7012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3860  -11.4448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0428  -14.6888    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6024  -12.2620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0056  -12.2372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8461  -13.7437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9663  -11.4531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7361  -13.4506    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2875  -11.0238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0015  -11.4283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5817  -11.4448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2751  -10.2066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1950  -15.3079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3902  -14.7961    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  4  1  0
  3  1  1  0
  4  1  1  0
  1  5  1  1
  6 18  1  0
  7  2  1  0
  8  6  1  0
  9  6  2  0
 10  5  1  0
 11  9  1  0
 12  8  1  0
 13 19  1  0
 14  4  1  0
 15 10  1  0
 16  7  1  0
 17 15  1  0
 18 21  1  0
 19 14  1  0
 20  3  2  0
 21 13  1  0
 15 22  1  1
 23  1  1  0
 24 10  2  0
 25 16  2  0
 26 17  2  0
 27 22  1  0
 28 22  2  0
 29  8  1  0
 30 16  1  0
 31 17  1  0
 32 33  2  0
 33 28  1  0
 34 27  2  0
 35 32  1  0
 36 23  1  0
  4 37  1  6
  2  3  1  0
  7 13  2  0
 32 34  1  0
 12 11  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA519374

   7-((Carboxy(4-hydroxyphenyl)acetyl)amino)-7-methoxy-(3-((1-methyl-1H-tetrazol-5-YL)thio)methyl)-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

2. Alternative Forms:

   

   ALA519374

   Moxalactam (sodium salt)

Molecule Features

Natural Product: Yes

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: 520.48

Molecular Weight (Monoisotopic): 520.1012

AlogP: -1.13

#Rotatable Bonds: 9

Polar Surface Area: 206.30

Molecular Species: ACID

HBA: 12

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 15

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 2.81

CX Basic pKa: ┄

CX LogP: 0.17

CX LogD: -6.72

Aromatic Rings: 2

Heavy Atoms: 36

QED Weighted: 0.13

Np Likeness Score: -0.37

References

1. Zhang E, Bai PY, Cui DY, Chu WC, Hua YG, Liu Q, Yin HY, Zhang YJ, Qin S, Liu HM..  (2018)  Synthesis and bioactivities study of new antibacterial peptide mimics: The dialkyl cationic amphiphiles.,  143  [PMID:29126736] [10.1016/j.ejmech.2017.10.044]

2. Tresse C, Radigue R, Gomes Von Borowski R, Thepaut M, Hanh Le H, Demay F, Georgeault S, Dhalluin A, Trautwetter A, Ermel G, Blanco C, van de Weghe P, Jean M, Giard JC, Gillet R..  (2019)  Synthesis and evaluation of 1,3,4-oxadiazole derivatives for development as broad-spectrum antibiotics.,  27  (21): [PMID:31540826] [10.1016/j.bmc.2019.115097]

3. Torosyan H, Shoichet BK..  (2019)  Protein Stability Effects in Aggregate-Based Enzyme Inhibition.,  62  (21): [PMID:31589047] [10.1021/acs.jmedchem.9b01019]

4. Bai PY,Qin SS,Chu WC,Yang Y,Cui DY,Hua YG,Yang QQ,Zhang E.  (2018)  Synthesis and antibacterial bioactivities of cationic deacetyl linezolid amphiphiles.,  155  [PMID:29966917] [10.1016/j.ejmech.2018.06.054]

Source

Source(1):

• Scientific Literature