2,3,5,6-Tetramethyl-terephthalic acid mono-[(S)-3-((S)-2-benzyloxycarbonylamino-3-phenyl-propionylamino)-2-oxo-butyl] ester

ID: ALA293581

PubChem CID: 10031289

Max Phase: Preclinical

Molecular Formula: C33H36N2O8

Molecular Weight: 588.66

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1c(C)c(C(=O)OCC(=O)[C@H](C)NC(=O)[C@H](Cc2ccccc2)NC(=O)OCc2ccccc2)c(C)c(C)c1C(=O)O

Standard InChI:  InChI=1S/C33H36N2O8/c1-19-21(3)29(22(4)20(2)28(19)31(38)39)32(40)42-18-27(36)23(5)34-30(37)26(16-24-12-8-6-9-13-24)35-33(41)43-17-25-14-10-7-11-15-25/h6-15,23,26H,16-18H2,1-5H3,(H,34,37)(H,35,41)(H,38,39)/t23-,26-/m0/s1

Standard InChI Key:  FRWIHAGJDZJUAP-OZXSUGGESA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA293581

   2,3,5,6-tetramethyl-4-[(3S)-2-oxo-3-[[(2S)-3-phenyl-2-(phenylmethoxycarbonylamino)propanoyl]amino]butoxy]carbonylbenzoic acid

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: 588.66

Molecular Weight (Monoisotopic): 588.2472

AlogP: 4.39

#Rotatable Bonds: 12

Polar Surface Area: 148.10

Molecular Species: ACID

HBA: 7

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.38

CX Basic pKa: ┄

CX LogP: 6.42

CX LogD: 3.01

Aromatic Rings: 3

Heavy Atoms: 43

QED Weighted: 0.26

Np Likeness Score: -0.12

References

1. Wagner BM, Smith RA, Coles PJ, Copp LJ, Ernest MJ, Krantz A..  (1994)  In vivo inhibition of cathepsin B by peptidyl (acyloxy)methyl ketones.,  37  (12): [PMID:8021922] [10.1021/jm00038a012]

Source

Source(1):

• Scientific Literature