tert-Butyl(S)-1-((S)-2-((S)-1-(bis(4-(methylthio)phenoxy)phosphoryl)-2-methylpropylcarbamoyl)pyrrolidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamate

ID: ALA2163492

PubChem CID: 60195915

Max Phase: Preclinical

Molecular Formula: C33H48N3O7PS2

Molecular Weight: 693.87

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CSc1ccc(OP(=O)(Oc2ccc(SC)cc2)[C@H](NC(=O)[C@@H]2CCCN2C(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)C)C(C)C)cc1

Standard InChI:  InChI=1S/C33H48N3O7PS2/c1-21(2)28(34-32(39)41-33(5,6)7)31(38)36-20-10-11-27(36)29(37)35-30(22(3)4)44(40,42-23-12-16-25(45-8)17-13-23)43-24-14-18-26(46-9)19-15-24/h12-19,21-22,27-28,30H,10-11,20H2,1-9H3,(H,34,39)(H,35,37)/t27-,28-,30-/m0/s1

Standard InChI Key:  MYIQHDSRNXKCMI-XEVVZDEMSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA2163492

   tert-butyl N-[(2S)-1-[(2S)-2-[[(1S)-1-bis(4-methylsulfanylphenoxy)phosphoryl-2-methylpropyl]carbamoyl]pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]carbamate

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: 693.87

Molecular Weight (Monoisotopic): 693.2671

AlogP: 7.42

#Rotatable Bonds: 13

Polar Surface Area: 123.27

Molecular Species: NEUTRAL

HBA: 9

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 10

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.68

CX Basic pKa: ┄

CX LogP: 6.70

CX LogD: 6.70

Aromatic Rings: 2

Heavy Atoms: 46

QED Weighted: 0.16

Np Likeness Score: -0.58

References

1. Winiarski Ł, Oleksyszyn J, Sieńczyk M..  (2012)  Human neutrophil elastase phosphonic inhibitors with improved potency of action.,  55  (14): [PMID:22720718] [10.1021/jm300599x]

2. Schulz-Fincke AC, Blaut M, Braune A, Gütschow M..  (2018)  A BODIPY-Tagged Phosphono Peptide as Activity-Based Probe for Human Leukocyte Elastase.,  9  (4): [PMID:29670698] [10.1021/acsmedchemlett.7b00533]

Source

Source(1):

• Scientific Literature