(Z)-methyl 4-(3-((4R,5S,E)-5-hydroxy-4-methylhex-2-enyl)phenyl)-3-methylbut-2-enoate

ID: ALA2286000

PubChem CID: 76316364

Max Phase: Preclinical

Molecular Formula: C19H26O3

Molecular Weight: 302.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)/C=C(/C)Cc1cccc(C/C=C/[C@@H](C)[C@H](C)O)c1

Standard InChI:  InChI=1S/C19H26O3/c1-14(12-19(21)22-4)11-18-10-6-9-17(13-18)8-5-7-15(2)16(3)20/h5-7,9-10,12-13,15-16,20H,8,11H2,1-4H3/b7-5+,14-12-/t15-,16+/m1/s1

Standard InChI Key:  VQSHUKAVMYZJNC-PIRBUOMWSA-N

Molfile:  

     RDKit          2D

 22 22  0  0  0  0  0  0  0  0999 V2000
   34.7086   -1.8655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7074   -2.6850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4155   -3.0940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1251   -2.6845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1223   -1.8619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4137   -1.4566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8335   -3.0920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5406   -2.6823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.2489   -3.0898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5393   -1.8651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9994   -3.0930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2920   -2.6839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5840   -3.0919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8766   -2.6828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1686   -3.0908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4612   -2.6816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1679   -3.9080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.8772   -1.8656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.2502   -3.9070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5436   -4.3194    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.9590   -4.3171    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.8340   -3.9141    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  1  0
  8  9  2  0
  8 10  1  0
  2 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  1
 14 18  1  6
  9 19  1  0
 19 20  1  0
 19 21  2  0
 20 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2286000

   methyl (Z)-4-[3-[(E,4R,5S)-5-hydroxy-4-methylhex-2-enyl]phenyl]-3-methylbut-2-enoate

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: 302.41

Molecular Weight (Monoisotopic): 302.1882

AlogP: 3.46

#Rotatable Bonds: 7

Polar Surface Area: 46.53

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.40

CX LogD: 4.40

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.48

Np Likeness Score: 1.28

References

1. Clinch K.  (1996)  Synthesis of analogues of monic acids A and C: Potential herbicides and inhibitors of isoleucyl tRNA synthetase,  6  (4): [10.1016/0960-894X(96)00050-9]

Source

Source(1):

• Scientific Literature