(S)-methyl 2-(3-(4-isopropylphenyl)acrylamido)-4-methylpentanoate

ID: ALA2285890

PubChem CID: 76327288

Max Phase: Preclinical

Molecular Formula: C19H27NO3

Molecular Weight: 317.43

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C19H27NO3/c1-13(2)12-17(19(22)23-5)20-18(21)11-8-15-6-9-16(10-7-15)14(3)4/h6-11,13-14,17H,12H2,1-5H3,(H,20,21)/b11-8+/t17-/m0/s1

Standard InChI Key:  QXJXKOKMDQIRKO-YRYLYKBFSA-N

Molfile:  

     RDKit          2D

 23 23  0  0  0  0  0  0  0  0999 V2000
   16.8129  -18.1102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8118  -18.9298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5198  -19.3387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2295  -18.9293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2266  -18.1066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5180  -17.7014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9378  -19.3368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6449  -18.9271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3532  -19.3346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0603  -18.9249    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.3545  -20.1518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.7687  -19.3323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4757  -18.9226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1841  -19.3301    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.4744  -18.1055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.7699  -20.1495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4783  -20.5570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4796  -21.3742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1853  -20.1473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8911  -18.9204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1051  -17.7018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1049  -16.8846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3975  -18.1106    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
 10 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 12 16  1  6
 16 17  1  0
 17 18  1  0
 17 19  1  0
 14 20  1  0
  1 21  1  0
 21 22  1  0
 21 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2285890

   methyl (2S)-4-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: 317.43

Molecular Weight (Monoisotopic): 317.1991

AlogP: 3.53

#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: 13.27

CX Basic pKa: ┄

CX LogP: 4.24

CX LogD: 4.24

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.62

Np Likeness Score: -0.09

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