US9156810, (46, 47)::US9156810, 46/47

ID: ALA3964563

PubChem CID: 10046549

Max Phase: Preclinical

Molecular Formula: C24H32O5

Molecular Weight: 400.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)C(=O)[C@H](C/C=C\CCCC(=O)O)[C@@H](/C=C/C(O)Cc2ccccc2)[C@@H]1O

Standard InChI:  InChI=1S/C24H32O5/c1-24(2)22(28)19(12-8-3-4-9-13-21(26)27)20(23(24)29)15-14-18(25)16-17-10-6-5-7-11-17/h3,5-8,10-11,14-15,18-20,23,25,29H,4,9,12-13,16H2,1-2H3,(H,26,27)/b8-3-,15-14+/t18?,19-,20-,23+/m1/s1

Standard InChI Key:  BHGLRNRVCYDAJB-PGLZQVPMSA-N

Molfile:  

     RDKit          2D

 29 30  0  0  1  0  0  0  0  0999 V2000
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    7.5445   -6.5046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2353   -7.4858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5408   -5.3899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7833   -4.2146    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1894   -6.0109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8912   -5.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8933   -3.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5951   -3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5548   -3.6021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -1.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3273   -7.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2042   -8.4833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7811   -8.0065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6560   -8.9997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9527  -10.4709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8276  -11.4642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1243  -12.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0008  -13.9287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2364  -15.1050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1383  -13.5463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7945   -7.8036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2826   -8.8999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  6
  4  6  1  0
  6  7  1  1
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
  6 18  1  0
 18 19  1  6
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 18 28  1  0
 28  2  1  0
 28 29  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3964563

   (Z)-7-[(1R,4S,5R)-4-hydroxy-5-[(E)-3-hydroxy-4-phenylbut-1-enyl]-3,3-dimethyl-2-oxocyclopentyl]hept-5-enoic acid

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: 400.52

Molecular Weight (Monoisotopic): 400.2250

AlogP: 3.55

#Rotatable Bonds: 10

Polar Surface Area: 94.83

Molecular Species: ACID

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.30

CX Basic pKa: ┄

CX LogP: 4.12

CX LogD: 1.16

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.41

Np Likeness Score: 1.59

References

1.  (2015)  Treatment of inflammatory bowel disease, 

Source

Source(1):

• BindingDB Database