(2S,3S)-ethyl 2-(3-(4-chlorophenyl)acrylamido)-3-methylpentanoate

ID: ALA2289690

PubChem CID: 76309378

Max Phase: Preclinical

Molecular Formula: C17H22ClNO3

Molecular Weight: 323.82

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)[C@@H](NC(=O)/C=C/c1ccc(Cl)cc1)[C@@H](C)CC

Standard InChI:  InChI=1S/C17H22ClNO3/c1-4-12(3)16(17(21)22-5-2)19-15(20)11-8-13-6-9-14(18)10-7-13/h6-12,16H,4-5H2,1-3H3,(H,19,20)/b11-8+/t12-,16-/m0/s1

Standard InChI Key:  RAOJRQKRWABFTP-YBXGNVEJSA-N

Molfile:  

     RDKit          2D

 22 22  0  0  0  0  0  0  0  0999 V2000
   17.4444   -9.5916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4432  -10.4112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1513  -10.8201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8609  -10.4107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8581   -9.5880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1495   -9.1828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5693  -10.8182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2764  -10.4085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9847  -10.8160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6918  -10.4063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.9860  -11.6332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.4001  -10.8137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1072  -10.4040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8155  -10.8115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.1059   -9.5869    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.4014  -11.6309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6943  -12.0406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1097  -12.0384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1110  -12.8556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5226  -10.4018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2309  -10.8093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7366   -9.1832    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  4  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 12 10  1  6
 12 13  1  0
 13 14  1  0
 13 15  2  0
 12 16  1  0
 16 17  1  6
 16 18  1  0
 18 19  1  0
 14 20  1  0
 20 21  1  0
  1 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2289690

   ethyl (2S,3S)-2-[[(E)-3-(4-chlorophenyl)prop-2-enoyl]amino]-3-methylpentanoate

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: 323.82

Molecular Weight (Monoisotopic): 323.1288

AlogP: 3.45

#Rotatable Bonds: 7

Polar Surface Area: 55.40

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.68

CX Basic pKa: ┄

CX LogP: 4.04

CX LogD: 4.04

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.62

Np Likeness Score: -0.46

References

1. ZHU J, KOBAMOTO N, YASUDA M, TAWATA S.  (2000)  Synthesis and Fungitoxic Activity of N-Cinnamoyl--Amino Acid Esters,  25  (3): [10.1584/jpestics.25.259]

Source

Source(1):

• Scientific Literature