(S)-5-(3-methoxy-4-(pent-2-ynyloxy)phenethylamino)-4-(methylsulfonamido)-5-oxopentanoic acid

ID: ALA2287021

PubChem CID: 11419310

Max Phase: Preclinical

Molecular Formula: C20H28N2O7S

Molecular Weight: 440.52

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C20H28N2O7S/c1-4-5-6-13-29-17-9-7-15(14-18(17)28-2)11-12-21-20(25)16(8-10-19(23)24)22-30(3,26)27/h7,9,14,16,22H,4,8,10-13H2,1-3H3,(H,21,25)(H,23,24)/t16-/m0/s1

Standard InChI Key:  WDPCEEYEKATBOM-INIZCTEOSA-N

Molfile:  

     RDKit          2D

 30 30  0  0  0  0  0  0  0  0999 V2000
   16.8391  -23.3147    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   17.5468  -22.9061    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.1314  -22.9061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4264  -24.0205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.2436  -24.0205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2545  -23.3147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9622  -22.9061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2545  -24.1319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6699  -23.3147    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.9622  -22.0889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.3776  -22.9061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0853  -23.3147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7931  -22.9061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4997  -23.3187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2069  -22.9108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2073  -22.0928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4946  -21.6843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7903  -22.0946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9144  -23.3198    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.9140  -24.1370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9145  -21.6832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.6227  -22.0909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3299  -21.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0346  -21.2676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7403  -20.8549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4503  -21.2595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9622  -24.5405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9622  -25.3577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2545  -25.7663    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.6699  -25.7663    0.0000 O   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
  8 27  1  0
 27 28  1  0
 28 29  2  0
 28 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2287021

   (4S)-4-(methanesulfonamido)-5-[2-(3-methoxy-4-pent-2-ynoxyphenyl)ethylamino]-5-oxopentanoic acid

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: 440.52

Molecular Weight (Monoisotopic): 440.1617

AlogP: 0.93

#Rotatable Bonds: 12

Polar Surface Area: 131.03

Molecular Species: ACID

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.81

CX Basic pKa: ┄

CX LogP: 1.01

CX LogD: -2.25

Aromatic Rings: 1

Heavy Atoms: 30

QED Weighted: 0.41

Np Likeness Score: -0.37

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