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

ID: ALA2289676

PubChem CID: 76327510

Max Phase: Preclinical

Molecular Formula: C20H29NO3

Molecular Weight: 331.46

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C20H29NO3/c1-6-15(5)19(20(23)24-7-2)21-18(22)13-10-16-8-11-17(12-9-16)14(3)4/h8-15,19H,6-7H2,1-5H3,(H,21,22)/b13-10+/t15-,19-/m0/s1

Standard InChI Key:  PFTUEJFFBNMZFV-GTWLYFKLSA-N

Molfile:  

     RDKit          2D

 24 24  0  0  0  0  0  0  0  0999 V2000
   16.8005  -22.4356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7994  -23.2551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5074  -23.6641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2171  -23.2546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2143  -22.4320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5056  -22.0267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9254  -23.6621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6325  -23.2524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3409  -23.6599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0479  -23.2502    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.3421  -24.4771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.7563  -23.6577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4633  -23.2480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1717  -23.6555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.4621  -22.4308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.7576  -24.4749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0505  -24.8846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4659  -24.8824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4672  -25.6995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8788  -23.2458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5871  -23.6532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0927  -22.0272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0925  -21.2100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3851  -22.4359    0.0000 C   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
 22 23  1  0
 22 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2289676

   ethyl (2S,3S)-3-methyl-2-[[(E)-3-(4-propan-2-ylphenyl)prop-2-enoyl]amino]pentanoate

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: 331.46

Molecular Weight (Monoisotopic): 331.2147

AlogP: 3.92

#Rotatable Bonds: 8

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: 13.25

CX Basic pKa: ┄

CX LogP: 4.68

CX LogD: 4.68

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.58

Np Likeness Score: -0.26

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