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

ID: ALA2286011

PubChem CID: 76323711

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-ICVCWPBISA-N

Molfile:  

     RDKit          2D

 22 22  0  0  0  0  0  0  0  0999 V2000
   22.2278   -1.6013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2267   -2.4209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9347   -2.8298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6444   -2.4204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6416   -1.5977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9329   -1.1925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3527   -2.8279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0598   -2.4182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7682   -2.8257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0585   -1.6010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5187   -2.8289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8113   -2.4197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1032   -2.8278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3959   -2.4186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6878   -2.8267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9804   -2.4175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6872   -3.6438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3965   -1.6014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4752   -2.4159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1848   -2.8216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.4751   -1.5970    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.1882   -3.6388    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:

   

   ALA2286011

   methyl (E)-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