2-(((Z)-(1-(2-aminothiazol-4-yl)-2-(((2S,3S)-1-((3-ethoxy-2,2-dimethyl-3-oxopropoxy)sulfonyl)-2-methyl-4-oxoazetidin-3-yl)amino)-2-oxoethylidene)amino)oxy)-2-methylpropanoic acid Trifluoro acetic acid

ID: ALA4457378

PubChem CID: 155525457

Max Phase: Preclinical

Molecular Formula: C22H30F3N5O12S2

Molecular Weight: 563.61

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCOC(=O)C(C)(C)COS(=O)(=O)N1C(=O)[C@@H](NC(=O)/C(=N\OC(C)(C)C(=O)O)c2csc(N)n2)[C@@H]1C.O=C(O)C(F)(F)F

Standard InChI:  InChI=1S/C20H29N5O10S2.C2HF3O2/c1-7-33-17(30)19(3,4)9-34-37(31,32)25-10(2)12(15(25)27)23-14(26)13(11-8-36-18(21)22-11)24-35-20(5,6)16(28)29;3-2(4,5)1(6)7/h8,10,12H,7,9H2,1-6H3,(H2,21,22)(H,23,26)(H,28,29);(H,6,7)/b24-13-;/t10-,12-;/m0./s1

Standard InChI Key:  YRZBSSPEOYULHU-AEPPIMKMSA-N

Molfile:  

     RDKit          2D

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   13.3486   -3.7246    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   11.3031   -7.9450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8947   -7.2326    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.4819   -7.9424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6196   -6.0994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0362   -6.8159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4484   -6.0969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7870   -6.0494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.7782   -5.4160    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9814   -5.6295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3981   -5.0463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7679   -6.4264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6116   -4.2495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6013   -5.2598    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3878   -6.0565    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3775   -7.0669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5807   -7.2804    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9608   -7.6501    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3776   -3.9555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3345   -3.1317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5376   -2.9182    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.0884   -3.6101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9755   -2.6127    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.6088   -6.8197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3235   -7.2317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7523   -7.2307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7512   -8.0556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4673   -6.8193    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1812   -7.2327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8962   -6.8212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  0
  1  5  1  0
  1  6  1  0
  1  7  1  0
  9  8  2  0
 10  9  2  0
 12 11  1  0
 13 12  1  0
 15 14  1  0
 16 15  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 17  1  0
 18 21  2  0
 20 22  1  6
 17 23  1  1
 23 24  1  0
 24 25  1  0
 24 26  2  0
 25 27  1  0
 25 28  2  0
 28 29  1  0
 29 15  1  0
 15 30  1  0
 30 31  1  0
 30 32  2  0
 27 33  1  0
 33 34  2  0
 34 35  1  0
 35 36  1  0
 36 27  2  0
 34 37  1  0
 19  9  1  0
  9 38  1  0
 38 39  1  0
 39 12  1  0
 12 40  1  0
 40 41  2  0
 40 42  1  0
 42 43  1  0
 43 44  1  0
M  END

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: 563.61

Molecular Weight (Monoisotopic): 563.1356

AlogP: -0.12

#Rotatable Bonds: 12

Polar Surface Area: 216.88

Molecular Species: ACID

HBA: 13

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 15

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 2.87

CX Basic pKa: 3.91

CX LogP: 0.68

CX LogD: -2.05

Aromatic Rings: 1

Heavy Atoms: 37

QED Weighted: 0.13

Np Likeness Score: 0.01

References

1. Gordon EM, Duncton MAJ, Wang BJ, Qi L, Fan D, Li X, Ni ZJ, Ding P, Grygorash R, Low E, Yu G, Sun J..  (2020)  Toward Orally Absorbed Prodrugs of the Antibiotic Aztreonam. Design of Novel Prodrugs of Sulfate Containing Drugs. Part 2.,  11  (2): [PMID:32071683] [10.1021/acsmedchemlett.9b00534]

Source

Source(1):

• Scientific Literature