[(S)-2-Thiophen-2-yl-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: ALA113706

PubChem CID: 44342511

Max Phase: Preclinical

Molecular Formula: C20H21N3O6S2

Molecular Weight: 463.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(N[C@@H](Cc1cccs1)C(=O)N[C@@H]1C(=O)N2CCS(=O)(=O)[C@@H]12)OCc1ccccc1

Standard InChI:  InChI=1S/C20H21N3O6S2/c24-17(22-16-18(25)23-8-10-31(27,28)19(16)23)15(11-14-7-4-9-30-14)21-20(26)29-12-13-5-2-1-3-6-13/h1-7,9,15-16,19H,8,10-12H2,(H,21,26)(H,22,24)/t15-,16+,19-/m0/s1

Standard InChI Key:  YAGNDONYTVCOFN-FCEWJHQRSA-N

Molfile:  

     RDKit          2D

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   -0.3375   -3.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.7055   -1.4541    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1 32  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA113706

   [(S)-2-Thiophen-2-yl-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: 463.54

Molecular Weight (Monoisotopic): 463.0872

AlogP: 0.67

#Rotatable Bonds: 7

Polar Surface Area: 121.88

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.45

CX Basic pKa: ┄

CX LogP: 0.79

CX LogD: 0.79

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.58

Np Likeness Score: -0.87

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