N-((S)-1-((S,E)-1-(benzylsulfonyl)-1-fluoro-5-phenylpent-1-en-3-ylamino)-1-oxo-3-p-tolylpropan-2-yl)-2,3-dihydrobenzo[b][1,4]dioxine-6-carboxamide

ID: ALA4878537

PubChem CID: 164625850

Max Phase: Preclinical

Molecular Formula: C37H37FN2O6S

Molecular Weight: 656.78

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1ccc(C[C@H](NC(=O)c2ccc3c(c2)OCCO3)C(=O)N[C@H](/C=C(\F)S(=O)(=O)Cc2ccccc2)CCc2ccccc2)cc1

Standard InChI:  InChI=1S/C37H37FN2O6S/c1-26-12-14-28(15-13-26)22-32(40-36(41)30-17-19-33-34(23-30)46-21-20-45-33)37(42)39-31(18-16-27-8-4-2-5-9-27)24-35(38)47(43,44)25-29-10-6-3-7-11-29/h2-15,17,19,23-24,31-32H,16,18,20-22,25H2,1H3,(H,39,42)(H,40,41)/b35-24+/t31-,32-/m0/s1

Standard InChI Key:  IPDSBUPCTOYGAS-JUTMOGOBSA-N

Molfile:  

 
     RDKit          2D

 47 51  0  0  0  0  0  0  0  0999 V2000
    8.4526  -14.3297    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0440  -13.6199    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.6350  -14.3271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3566  -13.6240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0685  -13.2113    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7803  -13.6240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3566  -14.4453    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6448  -13.2154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7803  -14.4453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4922  -13.2113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2040  -13.6240    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9117  -13.2113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4922  -12.3899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4922  -14.8580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4877  -15.6804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1987  -16.0889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9074  -15.6803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9047  -14.8547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1973  -14.4458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6235  -13.6240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3354  -13.2113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9117  -12.3899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2040  -11.9813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2040  -11.1600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9138  -10.7488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9141   -9.9282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2059   -9.5188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4917   -9.9318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4948  -10.7510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3344  -12.3899    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.7497  -13.2071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4683  -13.6285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4599  -14.4505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1683  -14.8676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8837  -14.4593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8863  -13.6338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1773  -13.2245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6477  -12.3935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9367  -11.9850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9422  -13.6271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2307  -13.2222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2293  -12.3962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4830  -11.9866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2039  -12.3985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1970  -13.2245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4857  -13.6387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6156  -16.0879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  1  0
  5  6  1  0
  4  7  2  0
  4  8  1  0
  6  9  1  6
  6 10  1  0
 10 11  1  0
 11 12  1  0
 10 13  2  0
  9 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 12 20  1  0
 20 21  2  0
 21  2  1  0
 12 22  1  1
 22 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 24  1  0
 21 30  1  0
  2 31  1  0
 31 32  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
  8 38  2  0
 38 39  1  0
 39 42  2  0
 41 40  2  0
 40  8  1  0
 41 42  1  0
 41 46  1  0
 42 43  1  0
 43 44  1  0
 44 45  1  0
 45 46  1  0
 17 47  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4878537

   ---

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: 656.78

Molecular Weight (Monoisotopic): 656.2356

AlogP: 5.65

#Rotatable Bonds: 13

Polar Surface Area: 110.80

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 13.72

CX Basic pKa: ┄

CX LogP: 6.60

CX LogD: 6.60

Aromatic Rings: 4

Heavy Atoms: 47

QED Weighted: 0.19

Np Likeness Score: -0.40

References

1. Jung S, Fuchs N, Johe P, Wagner A, Diehl E, Yuliani T, Zimmer C, Barthels F, Zimmermann RA, Klein P, Waigel W, Meyr J, Opatz T, Tenzer S, Distler U, Räder HJ, Kersten C, Engels B, Hellmich UA, Klein J, Schirmeister T..  (2021)  Fluorovinylsulfones and -Sulfonates as Potent Covalent Reversible Inhibitors of the Trypanosomal Cysteine Protease Rhodesain: Structure-Activity Relationship, Inhibition Mechanism, Metabolism, and In Vivo Studies.,  64  (16.0): [PMID:34378914] [10.1021/acs.jmedchem.1c01002]

Source

Source(1):

• Scientific Literature