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

ID: ALA2286001

PubChem CID: 76316365

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-NRXGNISQSA-N

Molfile:  

     RDKit          2D

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    4.9224   -6.5499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9212   -7.3694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6293   -7.7784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3389   -7.3689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3361   -6.5463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6275   -6.1410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0473   -7.7764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7543   -7.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4627   -7.7742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7531   -6.5495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2132   -7.7774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5058   -7.3683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7978   -7.7763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0904   -7.3672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3824   -7.7752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6750   -7.3661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3817   -8.5924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0910   -6.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1698   -7.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8793   -7.7702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1697   -6.5455    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8827   -8.5874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4999   -8.1843    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  6
 12 23  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA2286001

   methyl (E)-4-[3-[[(2R,3R)-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