(R/S)-3-ethyl-N-(3-methoxy-4-(pent-2-ynyloxy)phenethyl)-2-(methylsulfonamido)pentanamide

ID: ALA2287019

PubChem CID: 11212798

Max Phase: Preclinical

Molecular Formula: C22H34N2O5S

Molecular Weight: 438.59

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCC#CCOc1ccc(CCNC(=O)C(NS(C)(=O)=O)C(CC)CC)cc1OC

Standard InChI:  InChI=1S/C22H34N2O5S/c1-6-9-10-15-29-19-12-11-17(16-20(19)28-4)13-14-23-22(25)21(18(7-2)8-3)24-30(5,26)27/h11-12,16,18,21,24H,6-8,13-15H2,1-5H3,(H,23,25)

Standard InChI Key:  IEINNMQIIGDPBV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 30  0  0  0  0  0  0  0  0999 V2000
   16.8061  -17.9617    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   17.5138  -17.5531    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.0984  -17.5531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3934  -18.6675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.2105  -18.6675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2215  -17.9617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9292  -17.5531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2215  -18.7789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6369  -17.9617    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.9292  -16.7359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.3446  -17.5531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0523  -17.9617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7600  -17.5531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4666  -17.9657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1739  -17.5578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1743  -16.7397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4616  -16.3313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7573  -16.7416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8814  -17.9668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.8810  -18.7839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8815  -16.3302    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.5897  -16.7379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2969  -16.3283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0015  -15.9146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7073  -15.5019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4173  -15.9065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5138  -19.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9292  -19.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9292  -20.0047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5138  -20.0047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  1  0
  1  4  2  0
  1  5  2  0
  2  6  1  0
  6  7  1  0
  6  8  1  0
  7  9  1  0
  7 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
 15 19  1  0
 19 20  1  0
 16 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  3  0
 24 25  1  0
 25 26  1  0
  8 27  1  0
  8 28  1  0
 28 29  1  0
 27 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2287019

   3-ethyl-2-(methanesulfonamido)-N-[2-(3-methoxy-4-pent-2-ynoxyphenyl)ethyl]pentanamide

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: 438.59

Molecular Weight (Monoisotopic): 438.2188

AlogP: 2.50

#Rotatable Bonds: 12

Polar Surface Area: 93.73

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.47

CX Basic pKa: ┄

CX LogP: 3.14

CX LogD: 3.13

Aromatic Rings: 1

Heavy Atoms: 30

QED Weighted: 0.49

Np Likeness Score: -0.54

References

1. Lamberth C.  (2010)  Amino acid chemistry in crop protection,  66  (36): [10.1016/j.tet.2010.06.008]

Source

Source(1):

• Scientific Literature