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

ID: ALA2289709

PubChem CID: 76313092

Max Phase: Preclinical

Molecular Formula: C18H25NO3

Molecular Weight: 303.40

Molecule Type: Small molecule

Names and Identifiers

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

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

Standard InChI Key:  INNIVCIZUXQBRU-OFAQMXQXSA-N

Molfile:  

     RDKit          2D

 22 22  0  0  0  0  0  0  0  0999 V2000
    0.6383   -9.0180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6372   -9.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3452  -10.2465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0549   -9.8370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0520   -9.0144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3434   -8.6091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7632  -10.2445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4703   -9.8348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1786  -10.2423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8857   -9.8326    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1799  -11.0595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5940  -10.2401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3011   -9.8304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0095  -10.2378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2998   -9.0132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5953  -11.0573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3037  -11.4647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3050  -12.2819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0107  -11.0550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7165   -9.8281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4249  -10.2356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7152   -9.0109    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
 20 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2289709

   propan-2-yl (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: 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: 13.23

CX Basic pKa: ┄

CX LogP: 3.77

CX LogD: 3.77

Aromatic Rings: 1

Heavy Atoms: 22

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