(2S,5R)-Methyl 2-(hydroxycarbamoyl)-3,3-dimethyl-7-oxo-4-thia-1-azaspiro[bicyclo[3.2.0]heptane-6,3'-pyrazole]-5'-carboxylate

ID: ALA4879076

PubChem CID: 164626423

Max Phase: Preclinical

Molecular Formula: C12H14N4O6S

Molecular Weight: 342.33

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COC(=O)C1=CC2(N=N1)C(=O)N1[C@@H](C(=O)ONO)C(C)(C)S[C@@H]12

Standard InChI:  InChI=1S/C12H14N4O6S/c1-11(2)6(8(18)22-15-20)16-9(19)12(10(16)23-11)4-5(13-14-12)7(17)21-3/h4,6,10,15,20H,1-3H3/t6-,10+,12?/m0/s1

Standard InChI Key:  TUDHZVJZOHKZTM-CNDFYXPKSA-N

Molfile:  

 
     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   32.8806  -14.2942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8764  -13.4694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0906  -13.2183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6089  -13.8882    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.0973  -14.5530    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.6929  -14.2821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9804  -14.6988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6974  -15.1074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8847  -15.1195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7097  -14.2946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7141  -15.1195    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.5001  -15.3702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4928  -14.0355    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   33.7014  -13.4655    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   34.7600  -16.1530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2120  -16.7696    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.5680  -16.3194    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.3013  -15.7028    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.8317  -12.4351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3806  -11.8193    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.0240  -12.2676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.7651  -11.4843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8279  -17.1024    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.2798  -17.7189    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
  7  6  1  0
  7  8  1  0
  1  9  1  0
  9 11  1  0
 10  1  1  0
 10 11  1  0
 11 12  1  0
 12  7  1  0
  7 13  1  0
 13 10  1  0
 10 14  1  6
 12 15  1  6
 15 16  2  0
 15 17  1  0
  9 18  2  0
  3 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 17 23  1  0
 23 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4879076

   ---

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: 342.33

Molecular Weight (Monoisotopic): 342.0634

AlogP: -0.25

#Rotatable Bonds: 3

Polar Surface Area: 129.89

Molecular Species: NEUTRAL

HBA: 10

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.32

CX LogP: 0.05

CX LogD: 0.05

Aromatic Rings: ┄

Heavy Atoms: 23

QED Weighted: 0.41

Np Likeness Score: 0.24

References

1. Alves NG, Bártolo I, Alves AJS, Fontinha D, Francisco D, Lopes SMM, Soares MIL, Simões CJV, Prudêncio M, Taveira N, Pinho E Melo TMVD..  (2021)  Synthesis and structure-activity relationships of new chiral spiro-β-lactams highly active against HIV-1 and Plasmodium.,  219  [PMID:33887681] [10.1016/j.ejmech.2021.113439]

Source

Source(1):

• Scientific Literature