(S,Z)-6-(2-(2-Aminothiazol-4-yl)-2-(((2-carboxypropan-2-yl)oxy)imino)acetamido)-2-((2-(5,6-dihydroxy-1,3-dioxoisoindolin-2-yl)ethyl)carbamoyl)-5-oxo-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazole-3-carboxylic Acid

ID: ALA4634190

PubChem CID: 146303944

Max Phase: Preclinical

Molecular Formula: C27H26N8O12S

Molecular Weight: 686.62

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)(O/N=C(\C(=O)N[C@H]1CN2CC(C(=O)NCCN3C(=O)c4cc(O)c(O)cc4C3=O)=C(C(=O)O)N2C1=O)c1csc(N)n1)C(=O)O

Standard InChI:  InChI=1S/C27H26N8O12S/c1-27(2,25(45)46)47-32-17(14-9-48-26(28)31-14)20(39)30-13-8-33-7-12(18(24(43)44)35(33)23(13)42)19(38)29-3-4-34-21(40)10-5-15(36)16(37)6-11(10)22(34)41/h5-6,9,13,36-37H,3-4,7-8H2,1-2H3,(H2,28,31)(H,29,38)(H,30,39)(H,43,44)(H,45,46)/b32-17-/t13-/m0/s1

Standard InChI Key:  NDBWOXXNCCSABA-JFLUISNFSA-N

Molfile:  

 
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M  END

Alternative Forms

1. Parent:

   

   ALA4634190

   ---

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: 686.62

Molecular Weight (Monoisotopic): 686.1391

AlogP: -1.97

#Rotatable Bonds: 11

Polar Surface Area: 294.69

Molecular Species: ACID

HBA: 15

HBD: 7

#RO5 Violations: 3

HBA (Lipinski): 20

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 1.96

CX Basic pKa: 3.93

CX LogP: -3.29

CX LogD: -8.98

Aromatic Rings: 2

Heavy Atoms: 48

QED Weighted: 0.06

Np Likeness Score: -0.32

References

1. Goldberg JA, Nguyen H, Kumar V, Spencer EJ, Hoyer D, Marshall EK, Cmolik A, O'Shea M, Marshall SH, Hujer AM, Hujer KM, Rudin SD, Domitrovic TN, Bethel CR, Papp-Wallace KM, Logan LK, Perez F, Jacobs MR, van Duin D, Kreiswirth BM, Bonomo RA, Plummer MS, van den Akker F..  (2020)  A γ-Lactam Siderophore Antibiotic Effective against Multidrug-Resistant Gram-Negative Bacilli.,  63  (11): [PMID:32420736] [10.1021/acs.jmedchem.0c00255]

2. Goldberg JA, Kumar V, Spencer EJ, Hoyer D, Marshall SH, Hujer AM, Hujer KM, Bethel CR, Papp-Wallace KM, Perez F, Jacobs MR, van Duin D, Kreiswirth BN, van den Akker F, Plummer MS, Bonomo RA..  (2021)  A γ-lactam siderophore antibiotic effective against multidrug-resistant Pseudomonas aeruginosa, Klebsiella pneumoniae, and Acinetobacter spp.,  220  [PMID:33933754] [10.1016/j.ejmech.2021.113436]

Source

Source(1):

• Scientific Literature