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

ID: ALA4865945

PubChem CID: 164621754

Max Phase: Preclinical

Molecular Formula: C13H15N3O5S

Molecular Weight: 325.35

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C13H15N3O5S/c1-4-21-9(19)6-5-13(15-14-6)10(20)16-7(8(17)18)12(2,3)22-11(13)16/h5,7,11H,4H2,1-3H3,(H,17,18)/t7-,11+,13?/m0/s1

Standard InChI Key:  YFLNEUWVMRJJRY-OIQCWEDUSA-N

Molfile:  

 
     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    3.1789  -13.7777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1748  -12.9527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3889  -12.7017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9073  -13.3715    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3957  -14.0365    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9912  -13.7655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2787  -14.1822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9958  -14.5908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1831  -14.6029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0080  -13.7780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0124  -14.6029    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7984  -14.8536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7911  -13.5188    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.9996  -12.9489    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0584  -15.6365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5102  -16.2530    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8663  -15.8029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5997  -15.1863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1301  -11.9184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6789  -11.3026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3223  -11.7509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0635  -10.9677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2557  -10.8002    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
M  END

Alternative Forms

1. Parent:

   

   ALA4865945

   ---

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: 325.35

Molecular Weight (Monoisotopic): 325.0732

AlogP: 0.78

#Rotatable Bonds: 3

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: 0.69

CX LogD: -2.76

Aromatic Rings: ┄

Heavy Atoms: 22

QED Weighted: 0.61

Np Likeness Score: 0.34

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