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

ID: ALA2287036

PubChem CID: 76316438

Max Phase: Preclinical

Molecular Formula: C20H30N2O5S

Molecular Weight: 410.54

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C20H30N2O5S/c1-6-7-8-13-27-17-10-9-16(14-18(17)26-4)11-12-21-20(23)19(15(2)3)22-28(5,24)25/h9-10,14-15,19,22H,6,11-13H2,1-5H3,(H,21,23)/t19-/m0/s1

Standard InChI Key:  SQEXMSSVJQJLTC-IBGZPJMESA-N

Molfile:  

     RDKit          2D

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    3.1593  -12.2496    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7439  -12.2496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0389  -13.3640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8560  -13.3640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8670  -12.6582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5747  -12.2496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8670  -13.4754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2824  -12.6582    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5747  -11.4324    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9901  -12.2496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6978  -12.6582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4055  -12.2496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1121  -12.6622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8194  -12.2543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8198  -11.4363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1071  -11.0278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4028  -11.4381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5269  -12.6633    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5265  -13.4805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5270  -11.0267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2352  -11.4344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9424  -11.0248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6470  -10.6111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3528  -10.1984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0628  -10.6030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5747  -13.8840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1593  -13.8840    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
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 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
M  END

Alternative Forms

1. Parent:

   

   ALA2287036

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

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: 410.54

Molecular Weight (Monoisotopic): 410.1875

AlogP: 1.72

#Rotatable Bonds: 10

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: 9.73

CX Basic pKa: ┄

CX LogP: 2.25

CX LogD: 2.24

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.57

Np Likeness Score: -0.71

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