US9447055, I

ID: ALA3975522

Cas Number: 2005486-31-5

PubChem CID: 122522051

Product Number: E647754, Order Now?

Max Phase: Phase

Molecular Formula: C30H34FN3O5S2

Molecular Weight: 599.75

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Ebopiprant | Obe022 | OBE-022 | OBE022

Canonical SMILES:  CC(C)[C@H](N)C(=O)OCC[C@H](NC(=O)[C@@H]1SCCN1S(=O)(=O)c1ccc(-c2ccccc2)cc1)c1ccc(F)cc1

Standard InChI:  InChI=1S/C30H34FN3O5S2/c1-20(2)27(32)30(36)39-18-16-26(23-8-12-24(31)13-9-23)33-28(35)29-34(17-19-40-29)41(37,38)25-14-10-22(11-15-25)21-6-4-3-5-7-21/h3-15,20,26-27,29H,16-19,32H2,1-2H3,(H,33,35)/t26-,27-,29-/m0/s1

Standard InChI Key:  UUIBKACUTXYSAK-YCVJPRETSA-N

Molfile:  

L-Valine, (3S)-3-[[[(2S)-3-([1,1'-biphenyl]-4-ylsulfonyl)-2-thiazolidinyl]car...
     RDKit          2D

 41 44  0  0  1  0  0  0  0  0999 V2000
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   16.3633   -4.0865    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.6271   -4.4589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8931   -4.0821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1999   -4.5293    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.4659   -4.1526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4252   -3.3287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6913   -2.9518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9980   -3.3991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2640   -3.0224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5709   -3.4696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8369   -3.0929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1436   -3.5402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   11.2234   -2.1984    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7727   -4.5999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   11.3862   -5.4944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3455   -4.6704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0387   -4.2232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6929   -5.9416    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   14.8524   -3.2581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7537   -5.2741    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   16.5681   -5.4056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9449   -4.6716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3092   -3.4036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8304   -2.7640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6447   -2.8954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9381   -3.6665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4171   -4.3061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6025   -4.1746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7526   -3.7981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2736   -3.1585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0881   -3.2900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3815   -4.0611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8603   -4.7007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0459   -4.5691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  1  3  2  0
  1  4  1  0
  4  5  1  0
  5  6  1  1
  6  7  1  0
  7  8  1  0
  8  9  1  6
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 13 17  1  1
 12 18  2  0
  8 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 23 22  1  0
 24 23  2  0
 19 24  1  0
 22 25  1  0
  6 26  2  0
  5 27  1  0
 27 28  1  0
 29 28  1  0
  4 29  1  0
  1 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 34 33  1  0
 35 34  2  0
 30 35  1  0
 33 36  1  0
 36 37  2  0
 37 38  1  0
 38 39  2  0
 40 39  1  0
 41 40  2  0
 36 41  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3975522

   Ebopiprant

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: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 599.75

Molecular Weight (Monoisotopic): 599.1924

AlogP: 4.33

#Rotatable Bonds: 11

Polar Surface Area: 118.80

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.72

CX Basic pKa: 7.48

CX LogP: 4.55

CX LogD: 4.21

Aromatic Rings: 3

Heavy Atoms: 41

QED Weighted: 0.32

Np Likeness Score: -0.82

References

1.  (2016)  α-amino esters of hydroxypropylthiazolidine carboxamide derivative and salt form, crystal polymorph thereof, 

2. Unpublished dataset, 

Source

Source(2):

• Clinical Candidates
• BindingDB Database