2-((S)-4-((Z)-2-(2-aminothiazol-4-yl)-2-((1,5-dihydroxy-4-oxo-1,4-dihydropyridin-2-yl)methoxyimino)acetamido)-3-oxoisoxazolidin-2-yl)-5-oxotetrahydrofuran-2-carboxylic acid

ID: ALA3265221

PubChem CID: 90656110

Max Phase: Preclinical

Molecular Formula: C19H18N6O11S

Molecular Weight: 538.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(/C(=N/OCc2cc(=O)c(O)cn2O)C(=O)N[C@H]2CON(C3(C(=O)O)CCC(=O)O3)C2=O)cs1

Standard InChI:  InChI=1S/C19H18N6O11S/c20-18-22-10(7-37-18)14(23-34-5-8-3-11(26)12(27)4-24(8)33)15(29)21-9-6-35-25(16(9)30)19(17(31)32)2-1-13(28)36-19/h3-4,7,9,27,33H,1-2,5-6H2,(H2,20,22)(H,21,29)(H,31,32)/b23-14-/t9-,19?/m0/s1

Standard InChI Key:  ZSPXDBNKZMUCRF-JNHCFAHKSA-N

Molfile:  

     RDKit          2D

 37 40  0  0  0  0  0  0  0  0999 V2000
   20.1774   -6.5935    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   20.9872   -6.4357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0893   -5.6169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3392   -5.2671    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.7795   -5.8720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9607   -5.7722    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.8113   -5.2176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5180   -5.6433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2399   -5.2440    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.5028   -6.4681    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.8264   -4.3927    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.5483   -3.9934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.9467   -5.6695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0147   -6.4902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8185   -6.6766    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.2440   -5.9698    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.7033   -5.3467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3906   -7.0297    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.1421   -7.4356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7165   -8.1423    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.2572   -8.7655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0170   -8.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9457   -7.6219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0708   -9.5692    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.8831   -7.0797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5631   -7.5406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.9449   -6.2567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.5636   -3.1686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2855   -2.7693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9924   -3.1998    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.7121   -2.8040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7316   -1.9788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0250   -1.5511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2991   -1.9485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0430   -0.7263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.4551   -1.5823    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.9742   -4.0246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  1  1  0
  5  6  1  0
  3  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
  7 11  2  0
 11 12  1  0
 13  9  1  1
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 13  1  0
 14 18  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 19  1  0
 15 19  1  0
 21 24  2  0
 19 25  1  0
 25 26  1  0
 25 27  2  0
 12 28  1  0
 28 29  1  0
 29 30  1  0
 29 34  2  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  1  0
 33 35  2  0
 32 36  1  0
 30 37  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3265221

   2-[(4S)-4-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(1,5-dihydroxy-4-oxopyridin-2-yl)methoxyimino]acetyl]amino]-3-oxo-1,2-oxazolidin-2-yl]-5-oxooxolane-2-carboxylic acid

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: 538.45

Molecular Weight (Monoisotopic): 538.0754

AlogP: -1.87

#Rotatable Bonds: 8

Polar Surface Area: 245.20

Molecular Species: ACID

HBA: 15

HBD: 5

#RO5 Violations: 2

HBA (Lipinski): 17

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 2.26

CX Basic pKa: 3.32

CX LogP: -2.31

CX LogD: -4.60

Aromatic Rings: 2

Heavy Atoms: 37

QED Weighted: 0.11

Np Likeness Score: 0.11

References

1. Starr J, Brown MF, Aschenbrenner L, Caspers N, Che Y, Gerstenberger BS, Huband M, Knafels JD, Lemmon MM, Li C, McCurdy SP, McElroy E, Rauckhorst MR, Tomaras AP, Young JA, Zaniewski RP, Shanmugasundaram V, Han S..  (2014)  Siderophore receptor-mediated uptake of lactivicin analogues in gram-negative bacteria.,  57  (9): [PMID:24694215] [10.1021/jm500219c]

Source

Source(1):

• Scientific Literature