(1'R,6R)-Sodium spiro[penicillanate-6,1'-(2-benzoyl-5-benzyloxycarbonyl(cyclopent-4-enyl))]

ID: ALA4860940

PubChem CID: 164612556

Max Phase: Preclinical

Molecular Formula: C27H24NNaO6S

Molecular Weight: 491.57

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC1(C)S[C@H]2N(C(=O)C23C(C(=O)OCc2ccccc2)=CCC3C(=O)c2ccccc2)[C@H]1C(=O)[O-].[Na+]

Standard InChI:  InChI=1S/C27H25NO6S.Na/c1-26(2)21(22(30)31)28-24(33)27(25(28)35-26)18(20(29)17-11-7-4-8-12-17)13-14-19(27)23(32)34-15-16-9-5-3-6-10-16;/h3-12,14,18,21,25H,13,15H2,1-2H3,(H,30,31);/q;+1/p-1/t18?,21-,25+,27?;/m0./s1

Standard InChI Key:  WSALHOWAIARFML-LBSPMHMNSA-M

Molfile:  

     RDKit          2D

 37 40  0  0  0  0  0  0  0  0999 V2000
   39.9690   -8.2788    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
   36.9555   -5.8787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7389   -5.0786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9111   -5.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6161   -5.8121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2616   -6.3318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.7690   -5.8706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.0565   -6.2872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.7736   -6.6959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9608   -6.7080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.7858   -5.8830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.7903   -6.7080    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.5762   -6.9587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.5689   -5.6239    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   37.7775   -5.0539    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   38.8362   -7.7416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.2881   -8.3581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.6442   -7.9080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   38.0715   -4.5631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.9586   -3.6668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.6734   -6.9122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8815   -7.7104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.8780   -6.6933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6731   -5.8950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8786   -5.6761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2904   -6.2557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5022   -7.0575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2964   -7.2727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4760   -3.0243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1747   -2.2581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6918   -1.6155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3910   -0.8498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5760   -0.7270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0624   -1.3762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3659   -2.1394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  2  1  0
  8  7  1  0
  8  9  1  0
  2 10  1  0
 10 12  1  0
 11  2  1  0
 11 12  1  0
 12 13  1  0
 13  8  1  0
  8 14  1  0
 14 11  1  0
 11 15  1  6
 13 16  1  6
 16 17  2  0
 16 18  1  0
 10 19  2  0
  3 20  1  0
 20 21  2  0
 20 22  1  0
  6 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 25  1  0
 22 31  1  0
 32 31  1  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
 35 36  1  0
 36 37  2  0
 37 32  1  0
M  CHG  2   1   1  18  -1
M  END

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: 491.57

Molecular Weight (Monoisotopic): 491.1403

AlogP: 3.69

#Rotatable Bonds: 6

Polar Surface Area: 100.98

Molecular Species: ACID

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.39

CX Basic pKa: ┄

CX LogP: 3.93

CX LogD: 0.52

Aromatic Rings: 2

Heavy Atoms: 35

QED Weighted: 0.37

Np Likeness Score: 0.59

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