(E)-methyl 4-(3-(((2S,3S)-3-((2S,3S)-3-hydroxybutan-2-yl)oxiran-2-yl)methyl)phenyl)-3-methylbut-2-enoate

ID: ALA2286002

PubChem CID: 76334529

Max Phase: Preclinical

Molecular Formula: C19H26O4

Molecular Weight: 318.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)/C=C(\C)Cc1cccc(C[C@@H]2O[C@H]2[C@@H](C)[C@H](C)O)c1

Standard InChI:  InChI=1S/C19H26O4/c1-12(9-18(21)22-4)8-15-6-5-7-16(10-15)11-17-19(23-17)13(2)14(3)20/h5-7,9-10,13-14,17,19-20H,8,11H2,1-4H3/b12-9+/t13-,14-,17-,19-/m0/s1

Standard InChI Key:  CSAWTXFZCCPLBA-NNFISCJFSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
   14.9144   -6.1826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9132   -7.0021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6213   -7.4111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3309   -7.0016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3281   -6.1790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6195   -5.7737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0393   -7.4091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7464   -6.9994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4547   -7.4069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7451   -6.1822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2052   -7.4101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4978   -7.0010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7898   -7.4090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0824   -6.9998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3744   -7.4079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6670   -6.9987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3737   -8.2251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0831   -6.1827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1618   -6.9972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8713   -7.4029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1617   -6.1782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8747   -8.2200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4919   -7.8170    0.0000 O   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  1  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
 13 23  1  1
 12 23  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA2286002

   methyl (E)-4-[3-[[(2S,3S)-3-[(2S,3S)-3-hydroxybutan-2-yl]oxiran-2-yl]methyl]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: 318.41

Molecular Weight (Monoisotopic): 318.1831

AlogP: 2.68

#Rotatable Bonds: 7

Polar Surface Area: 59.06

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.50

CX LogD: 3.50

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.48

Np Likeness Score: 1.40

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