(2S,3R)-3-hydroxy-N-(3-methoxy-4-(pent-2-ynyloxy)phenethyl)-2-(methylsulfonamido)butanamide

ID: ALA2287020

PubChem CID: 76323790

Max Phase: Preclinical

Molecular Formula: C19H28N2O6S

Molecular Weight: 412.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCC#CCOc1ccc(CCNC(=O)[C@@H](NS(C)(=O)=O)[C@@H](C)O)cc1OC

Standard InChI:  InChI=1S/C19H28N2O6S/c1-5-6-7-12-27-16-9-8-15(13-17(16)26-3)10-11-20-19(23)18(14(2)22)21-28(4,24)25/h8-9,13-14,18,21-22H,5,10-12H2,1-4H3,(H,20,23)/t14-,18+/m1/s1

Standard InChI Key:  WLRHPVZVBDFUMA-KDOFPFPSSA-N

Molfile:  

     RDKit          2D

 28 28  0  0  0  0  0  0  0  0999 V2000
    1.8323   -8.4323    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.5468   -8.0198    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1178   -8.0198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4156   -9.1448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2406   -9.1448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2612   -8.4323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9757   -8.0198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2612   -9.2573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6902   -8.4323    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9757   -7.1948    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4046   -8.0198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1191   -8.4323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8336   -8.0198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5469   -8.4364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2609   -8.0245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2614   -7.1987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5419   -6.7863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8308   -7.2005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9752   -8.4374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9748   -9.2624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9753   -6.7852    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6903   -7.1968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4042   -6.7833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1156   -6.3656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8281   -5.9490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5449   -6.3575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5468   -9.6698    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9757   -9.6698    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
  6  2  1  6
  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  1
  8 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2287020

   (2S,3R)-3-hydroxy-2-(methanesulfonamido)-N-[2-(3-methoxy-4-pent-2-ynoxyphenyl)ethyl]butanamide

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: 412.51

Molecular Weight (Monoisotopic): 412.1668

AlogP: 0.44

#Rotatable Bonds: 10

Polar Surface Area: 113.96

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.65

CX Basic pKa: ┄

CX LogP: 0.73

CX LogD: 0.71

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.48

Np Likeness Score: -0.50

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