[(S)-2-Cyclohexyl-1-((5S,6R)-4,4,7-trioxo-4lambda*6*-thia-1-aza-bicyclo[3.2.0]hept-6-ylcarbamoyl)-ethyl]-carbamic acid benzyl ester

ID: ALA114410

PubChem CID: 44342745

Max Phase: Preclinical

Molecular Formula: C22H29N3O6S

Molecular Weight: 463.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(N[C@@H](CC1CCCCC1)C(=O)N[C@@H]1C(=O)N2CCS(=O)(=O)[C@@H]12)OCc1ccccc1

Standard InChI:  InChI=1S/C22H29N3O6S/c26-19(24-18-20(27)25-11-12-32(29,30)21(18)25)17(13-15-7-3-1-4-8-15)23-22(28)31-14-16-9-5-2-6-10-16/h2,5-6,9-10,15,17-18,21H,1,3-4,7-8,11-14H2,(H,23,28)(H,24,26)/t17-,18+,21-/m0/s1

Standard InChI Key:  TWOOZSOQPIWDLA-UEXGIBASSA-N

Molfile:  

     RDKit          2D

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    8.3750   -4.0375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    9.1542   -4.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2042   -1.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5875   -2.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875   -2.4667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3917   -3.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7917   -0.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.5042   -0.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0792   -0.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3792   -4.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0167   -2.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0750    0.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5042    0.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7917   -3.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7917    1.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2156   -2.2253    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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 28 23  1  0
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 31 27  1  0
 32 29  1  0
  2  5  1  0
  8  9  1  0
 30 32  1  0
 28 31  2  0
  1 33  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA114410

   [(S)-2-Cyclohexyl-1-((5S,6R)-4,4,7-trioxo-4lambda*6*-thia-1-aza-bicyclo[3.2.0]hept-6-ylcarbamoyl)-ethyl]-carbamic acid benzyl ester

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 463.56

Molecular Weight (Monoisotopic): 463.1777

AlogP: 1.33

#Rotatable Bonds: 7

Polar Surface Area: 121.88

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.68

CX Basic pKa: ┄

CX LogP: 1.35

CX LogD: 1.35

Aromatic Rings: 1

Heavy Atoms: 32

QED Weighted: 0.59

Np Likeness Score: -0.25

References

1. Zhou NE, Kaleta J, Purisima E, Menard R, Micetich RG, Singh R..  (2002)  6-Acylamino-penam derivatives: synthesis and inhibition of cathepsins B, L, K, and S.,  12  (23): [PMID:12419374] [10.1016/s0960-894x(02)00766-7]

Source

Source(1):

• Scientific Literature