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

ID: ALA2287037

PubChem CID: 76334603

Max Phase: Preclinical

Molecular Formula: C21H32N2O5S

Molecular Weight: 424.56

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C21H32N2O5S/c1-6-8-9-14-28-18-11-10-17(15-19(18)27-4)12-13-22-21(24)20(16(3)7-2)23-29(5,25)26/h10-11,15-16,20,23H,6-7,12-14H2,1-5H3,(H,22,24)/t16-,20-/m0/s1

Standard InChI Key:  LKYLXLUQVZCTOA-JXFKEZNVSA-N

Molfile:  

     RDKit          2D

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    1.3241   -8.2467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6219   -9.3717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4469   -9.3717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.8964   -8.6592    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1819   -7.4217    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    7.7532   -8.6632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4672   -8.2514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.1815   -7.0121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8966   -7.4236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6105   -7.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3219   -6.5925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0344   -6.1758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7511   -6.5843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7530   -9.8967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1819   -9.8967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1819  -10.7217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  3  1  0
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  6  2  1  6
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 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  6
  8 28  1  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2287037

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

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: 424.56

Molecular Weight (Monoisotopic): 424.2032

AlogP: 2.11

#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: 9.59

CX Basic pKa: ┄

CX LogP: 2.69

CX LogD: 2.69

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.53

Np Likeness Score: -0.57

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