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

ID: ALA4857903

PubChem CID: 164609856

Max Phase: Preclinical

Molecular Formula: C15H19N3O5S

Molecular Weight: 353.40

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C15H19N3O5S/c1-13(2,3)23-10(21)7-6-15(17-16-7)11(22)18-8(9(19)20)14(4,5)24-12(15)18/h6,8,12H,1-5H3,(H,19,20)/t8-,12+,15?/m0/s1

Standard InChI Key:  HMZVNLLVDWAWBX-FNHPIHAZSA-N

Molfile:  

 
     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    9.1748  -13.7908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1705  -12.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3847  -12.7149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9031  -13.3848    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3914  -14.0497    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9871  -13.7787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2747  -14.1954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9917  -14.6041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1789  -14.6162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0038  -13.7912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0083  -14.6162    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7943  -14.8669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7870  -13.5321    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.9955  -12.9621    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0542  -15.6497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5061  -16.2664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8622  -15.8161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5955  -15.1995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1258  -11.9316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6747  -11.3158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3180  -11.7641    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0592  -10.9808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2514  -10.8133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6081  -10.3650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8414  -10.1788    0.0000 C   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
 22 23  1  0
 22 24  1  0
 22 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4857903

   ---

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: 353.40

Molecular Weight (Monoisotopic): 353.1045

AlogP: 1.56

#Rotatable Bonds: 2

Polar Surface Area: 108.63

Molecular Species: ACID

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.20

CX Basic pKa: ┄

CX LogP: 1.38

CX LogD: -2.06

Aromatic Rings: ┄

Heavy Atoms: 24

QED Weighted: 0.60

Np Likeness Score: 0.31

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