6-[3-(4-Acetyl-2-ethyl-5-hydroxy-phenoxy)-propoxy]-5-(2-carboxy-ethyl)-9-oxo-9H-xanthene-2-carboxylic acid

ID: ALA88337

PubChem CID: 9893718

Max Phase: Preclinical

Molecular Formula: C30H28O10

Molecular Weight: 548.54

Molecule Type: Small molecule

Names and Identifiers

Synonyms: LY-282210 | LY-282210|CHEMBL88337|BDBM50029482|L009647|6-[3-(4-Acetyl-2-ethyl-5-hydroxy-phenoxy)-propoxy]-5-(2-carboxy-ethyl)-9-oxo-9H-xanthene-2-carboxylic acid

Canonical SMILES:  CCc1cc(C(C)=O)c(O)cc1OCCCOc1ccc2c(=O)c3cc(C(=O)O)ccc3oc2c1CCC(=O)O

Standard InChI:  InChI=1S/C30H28O10/c1-3-17-13-21(16(2)31)23(32)15-26(17)39-12-4-11-38-24-9-6-20-28(35)22-14-18(30(36)37)5-8-25(22)40-29(20)19(24)7-10-27(33)34/h5-6,8-9,13-15,32H,3-4,7,10-12H2,1-2H3,(H,33,34)(H,36,37)

Standard InChI Key:  HGMXXGVRUCAMMK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 40 43  0  0  0  0  0  0  0  0999 V2000
    7.5417   -1.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5542   -0.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9792   -0.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2667    0.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2542   -1.5292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8375   -1.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4167   -0.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9750   -1.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1292    0.1333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6917    0.1083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4250   -1.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8500   -0.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1167    0.1083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3917   -0.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8292    0.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8417   -1.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1375   -1.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8292   -2.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2958    0.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1167   -3.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1250   -1.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2667    0.9458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1375    0.9583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8292   -0.3042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6792   -1.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4000   -4.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1167    0.9333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1167   -0.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3917   -1.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8292   -4.0042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3000    0.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1167   -2.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5625   -1.5167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4125   -1.5167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9875   -1.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1417   -2.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0083   -0.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2750   -1.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7000   -1.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4292   -2.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  8  2  0
  4  2  1  0
  5  1  1  0
  6  1  1  0
  7 11  1  0
  8  5  1  0
  9 12  1  0
 10  3  1  0
 11 17  2  0
 12 16  2  0
 13 14  1  0
 14 29  1  0
 15  2  1  0
 16 33  1  0
 17 16  1  0
 18  6  1  0
 19  7  1  0
 20 32  1  0
 21  6  2  0
 22  4  2  0
 23  9  1  0
 24 13  1  0
 25  8  1  0
 26 20  1  0
 27 13  2  0
 28 21  1  0
 29 25  2  0
 30 20  2  0
 31 19  2  0
 32 18  1  0
 33 38  1  0
 34 21  1  0
 35 39  1  0
 36 17  1  0
 37 19  1  0
 38 35  1  0
 39 34  1  0
 40 36  1  0
  3  4  1  0
 15 28  2  0
 14 10  2  0
  9  7  2  0
M  END

Alternative Forms

1. Alternative Forms:

   

   ALA88337

   Trisodium;6-[3-(4-acetyl-2-ethyl-5-oxidophenoxy)propoxy]-5-(2-carboxylatoethyl)-9-oxoxanthene-2-carboxylate

2. Parent:

   

   ALA88337

   6-[3-(4-Acetyl-2-ethyl-5-hydroxy-phenoxy)-propoxy]-5-(2-carboxy-ethyl)-9-oxo-9H-xanthene-2-carboxylic 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: 548.54

Molecular Weight (Monoisotopic): 548.1682

AlogP: 4.98

#Rotatable Bonds: 12

Polar Surface Area: 160.57

Molecular Species: ACID

HBA: 8

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.20

CX Basic pKa: ┄

CX LogP: 5.11

CX LogD: -1.41

Aromatic Rings: 4

Heavy Atoms: 40

QED Weighted: 0.13

Np Likeness Score: 0.34

References

1. Brooks CD, Summers JB..  (1996)  Modulators of leukotriene biosynthesis and receptor activation.,  39  (14): [PMID:8709092] [10.1021/jm960088k]

2. Sawyer JS, Baldwin RF, Sofia MJ, Floreancig P, Marder P, Saussy DL, Froelich LL, Silbaugh SA, Stengel PW, Cockerham SL..  (1993)  Biphenylyl-substituted xanthones: highly potent leukotriene B4 receptor antagonists.,  36  (24): [PMID:8254628] [10.1021/jm00076a030]

3. Sawyer JS, Bach NJ, Baker SR, Baldwin RF, Borromeo PS, Cockerham SL, Fleisch JH, Floreancig P, Froelich LL, Jackson WT..  (1995)  Synthetic and structure/activity studies on acid-substituted 2-arylphenols: discovery of 2-[2-propyl-3-[3-[2-ethyl-4-(4-fluorophenyl)-5- hydroxyphenoxy]-propoxy]phenoxy]benzoic acid, a high-affinity leukotriene B4 receptor antagonist.,  38  (22): [PMID:7473568] [10.1021/jm00022a006]

Source

Source(1):

• Scientific Literature