ethyl 3'-((4R,5S,E)-5-hydroxy-4-methylhex-2-enyl)biphenyl-3-carboxylate

ID: ALA2286005

PubChem CID: 76316366

Max Phase: Preclinical

Molecular Formula: C22H26O3

Molecular Weight: 338.45

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C22H26O3/c1-4-25-22(24)21-13-7-12-20(15-21)19-11-6-10-18(14-19)9-5-8-16(2)17(3)23/h5-8,10-17,23H,4,9H2,1-3H3/b8-5+/t16-,17+/m1/s1

Standard InChI Key:  QSANHAMAMZJGKE-VBXGELDYSA-N

Molfile:  

     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
    4.8357  -10.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8345  -11.7113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5426  -12.1202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2523  -11.7108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2494  -10.8881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5408  -10.4829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9606  -12.1183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1265  -12.1193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4191  -11.7101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7111  -12.1182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0037  -11.7090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2957  -12.1171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5883  -11.7079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2950  -12.9342    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0044  -10.8918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9570  -12.9358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6646  -13.3432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3726  -12.9335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3687  -12.1120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6606  -11.7083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0769  -11.6985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7866  -12.1034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0727  -10.8813    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7908  -12.9206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5006  -13.3256    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
  2  8  1  0
  8  9  1  0
  9 10  2  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
M  END

Alternative Forms

1. Parent:

   

   ALA2286005

   ethyl 3-[3-[(E,4R,5S)-5-hydroxy-4-methylhex-2-enyl]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: 338.45

Molecular Weight (Monoisotopic): 338.1882

AlogP: 4.65

#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: 5.26

CX LogD: 5.26

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.59

Np Likeness Score: 0.48

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