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

ID: ALA2287034

PubChem CID: 11269812

Max Phase: Preclinical

Molecular Formula: C20H28N2O5S

Molecular Weight: 408.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=CCC(NS(C)(=O)=O)C(=O)NCCc1ccc(OCC#CCC)c(OC)c1

Standard InChI:  InChI=1S/C20H28N2O5S/c1-5-7-8-14-27-18-11-10-16(15-19(18)26-3)12-13-21-20(23)17(9-6-2)22-28(4,24)25/h6,10-11,15,17,22H,2,5,9,12-14H2,1,3-4H3,(H,21,23)

Standard InChI Key:  FDJAWPOSXPLEAR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 28  0  0  0  0  0  0  0  0999 V2000
    2.9510   -7.7674    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.6587   -7.3588    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2433   -7.3588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5382   -8.4732    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3554   -8.4732    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3664   -7.7674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0741   -7.3588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3664   -8.5846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7818   -7.7674    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0741   -6.5417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4895   -7.3588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1972   -7.7674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9049   -7.3588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6115   -7.7715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3188   -7.3636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3192   -6.5455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6065   -6.1371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9022   -6.5473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0263   -7.7725    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0259   -8.5897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0264   -6.1360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7346   -6.5436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4418   -6.1341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1464   -5.7203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8522   -5.3076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5622   -5.7123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0741   -8.9932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0741   -9.8104    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
 27 28  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2287034

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

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: 408.52

Molecular Weight (Monoisotopic): 408.1719

AlogP: 1.64

#Rotatable Bonds: 11

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: 9.72

CX Basic pKa: ┄

CX LogP: 2.02

CX LogD: 2.02

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.43

Np Likeness Score: -0.41

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