ethyl 3'-(((2S,3S)-3-((2S,3S)-3-hydroxybutan-2-yl)oxiran-2-yl)methyl)biphenyl-3-carboxylate

ID: ALA2286007

PubChem CID: 76334530

Max Phase: Preclinical

Molecular Formula: C22H26O4

Molecular Weight: 354.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1cccc(-c2cccc(C[C@@H]3O[C@H]3[C@@H](C)[C@H](C)O)c2)c1

Standard InChI:  InChI=1S/C22H26O4/c1-4-25-22(24)19-10-6-9-18(13-19)17-8-5-7-16(11-17)12-20-21(26-20)14(2)15(3)23/h5-11,13-15,20-21,23H,4,12H2,1-3H3/t14-,15-,20-,21-/m0/s1

Standard InChI Key:  ODAMUZOWBAGWCD-PBFVBANWSA-N

Molfile:  

     RDKit          2D

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   26.2766  -10.6812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2755  -11.5008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9835  -11.9097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6932  -11.5003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6904  -10.6776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9818  -10.2724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4016  -11.9078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5675  -11.9088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8601  -11.4996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1521  -11.9077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4447  -11.4985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7366  -11.9066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0293  -11.4974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7360  -12.7238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.4453  -10.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3980  -12.7253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1055  -13.1327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8136  -12.7230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8096  -11.9016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1015  -11.4978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5178  -11.4880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2276  -11.8930    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.5137  -10.6708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.2318  -12.7101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9415  -13.1151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8542  -12.3157    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
  2  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  1
 11 15  1  6
  7 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20  7  1  0
 21 22  1  0
 21 23  2  0
 19 21  1  0
 22 24  1  0
 24 25  1  0
  9 26  1  1
 10 26  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA2286007

   ethyl 3-[3-[[(2S,3S)-3-[(2S,3S)-3-hydroxybutan-2-yl]oxiran-2-yl]methyl]phenyl]benzoate

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: 354.45

Molecular Weight (Monoisotopic): 354.1831

AlogP: 3.86

#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: 4.36

CX LogD: 4.36

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.61

Np Likeness Score: 0.59

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