(S)-N-(3-methoxy-4-(pent-2-ynyloxy)phenethyl)-2-(methylsulfonamido)propanamide

ID: ALA2287033

PubChem CID: 11349573

Max Phase: Preclinical

Molecular Formula: C18H26N2O5S

Molecular Weight: 382.48

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C18H26N2O5S/c1-5-6-7-12-25-16-9-8-15(13-17(16)24-3)10-11-19-18(21)14(2)20-26(4,22)23/h8-9,13-14,20H,5,10-12H2,1-4H3,(H,19,21)/t14-/m0/s1

Standard InChI Key:  XQGRUDHUGGVFEM-AWEZNQCLSA-N

Molfile:  

     RDKit          2D

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   16.7854   -2.9634    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   17.4931   -2.5548    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.0777   -2.5548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3727   -3.6691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1899   -3.6691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2009   -2.9634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9086   -2.5548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2009   -3.7805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6163   -2.9633    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.9086   -1.7376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.3240   -2.5548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0317   -2.9633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7394   -2.5548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4460   -2.9674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1532   -2.5595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1537   -1.7414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4410   -1.3330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7367   -1.7432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8607   -2.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.8604   -3.7856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8608   -1.3319    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.5691   -1.7395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2763   -1.3300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9809   -0.9162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6867   -0.5035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3966   -0.9082    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  6
  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
M  END

Alternative Forms

1. Parent:

   

   ALA2287033

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

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: 382.48

Molecular Weight (Monoisotopic): 382.1562

AlogP: 1.08

#Rotatable Bonds: 9

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: 10.33

CX Basic pKa: ┄

CX LogP: 1.36

CX LogD: 1.36

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.62

Np Likeness Score: -0.86

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