(S)-propyl 2-cinnamamido-4-methylpentanoate

ID: ALA2289708

PubChem CID: 76309381

Max Phase: Preclinical

Molecular Formula: C18H25NO3

Molecular Weight: 303.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCOC(=O)[C@H](CC(C)C)NC(=O)/C=C/c1ccccc1

Standard InChI:  InChI=1S/C18H25NO3/c1-4-12-22-18(21)16(13-14(2)3)19-17(20)11-10-15-8-6-5-7-9-15/h5-11,14,16H,4,12-13H2,1-3H3,(H,19,20)/b11-10+/t16-/m0/s1

Standard InChI Key:  WIALOHNAFPIMRL-OFAQMXQXSA-N

Molfile:  

     RDKit          2D

 22 22  0  0  0  0  0  0  0  0999 V2000
   33.5777   -4.5275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5766   -5.3471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2846   -5.7560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9943   -5.3466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9914   -4.5239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2828   -4.1187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7026   -5.7541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4097   -5.3444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1180   -5.7519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8251   -5.3422    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.1193   -6.5690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.5335   -5.7496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.2405   -5.3399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.9489   -5.7474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.2392   -4.5227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.5347   -6.5668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.2431   -6.9743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.2444   -7.7915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.9502   -6.5646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.6559   -5.3377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.3643   -5.7452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.0714   -5.3355    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
 20 21  1  0
 21 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2289708

   propyl (2S)-4-methyl-2-[[(E)-3-phenylprop-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: 303.40

Molecular Weight (Monoisotopic): 303.1834

AlogP: 3.18

#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: 13.23

CX Basic pKa: ┄

CX LogP: 3.88

CX LogD: 3.88

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.59

Np Likeness Score: -0.17

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