Spiro[penicillanic-6,3'-(5-hydroxycarbonyl-3H-pyrazole)]acid

ID: ALA4868227

PubChem CID: 164625131

Max Phase: Preclinical

Molecular Formula: C11H11N3O5S

Molecular Weight: 297.29

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC1(C)S[C@H]2N(C(=O)C23C=C(C(=O)O)N=N3)[C@H]1C(=O)O

Standard InChI:  InChI=1S/C11H11N3O5S/c1-10(2)5(7(17)18)14-8(19)11(9(14)20-10)3-4(6(15)16)12-13-11/h3,5,9H,1-2H3,(H,15,16)(H,17,18)/t5-,9+,11?/m0/s1

Standard InChI Key:  DPIFTYMPRMTHME-JJJLSQATSA-N

Molfile:  

 
     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
   21.1032  -14.7489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0990  -13.9239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3131  -13.6730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8316  -14.3429    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.3199  -15.0078    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.9156  -14.7368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2030  -15.1534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9201  -15.5622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1073  -15.5742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9323  -14.7493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9368  -15.5742    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.7227  -15.8248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7154  -14.4902    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   21.9240  -13.9202    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   22.9827  -16.6078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4346  -17.2244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.7907  -16.7742    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.5240  -16.1576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0543  -12.8897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6033  -12.2738    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2465  -12.7222    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
M  END

Alternative Forms

1. Parent:

   

   ALA4868227

   ---

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: 297.29

Molecular Weight (Monoisotopic): 297.0419

AlogP: 0.31

#Rotatable Bonds: 2

Polar Surface Area: 119.63

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.84

CX Basic pKa: ┄

CX LogP: -0.05

CX LogD: -6.92

Aromatic Rings: ┄

Heavy Atoms: 20

QED Weighted: 0.71

Np Likeness Score: 0.53

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