6-[2-Amino-2-(carboxymethyl-carbamoyl)-ethylsulfanyl]-9-(3-hexyloxy-phenyl)-5-hydroxy-non-7-enoic acid

ID: ALA3706608

PubChem CID: 122197297

Max Phase: Preclinical

Molecular Formula: C26H40N2O7S

Molecular Weight: 524.68

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCOc1cccc(C/C=C/[C@H](SC[C@H](N)C(=O)NCC(=O)O)[C@H](O)CCCC(=O)O)c1

Standard InChI:  InChI=1S/C26H40N2O7S/c1-2-3-4-5-15-35-20-11-6-9-19(16-20)10-7-13-23(22(29)12-8-14-24(30)31)36-18-21(27)26(34)28-17-25(32)33/h6-7,9,11,13,16,21-23,29H,2-5,8,10,12,14-15,17-18,27H2,1H3,(H,28,34)(H,30,31)(H,32,33)/b13-7+/t21-,22+,23-/m0/s1

Standard InChI Key:  RYSYWWLALYEJEN-HTACPVTASA-N

Molfile:  

     RDKit          2D

 36 36  0  0  1  0  0  0  0  0999 V2000
    3.7500   -6.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4667   -6.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7542   -5.3542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7500   -7.8292    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.0417   -4.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3250   -9.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4625   -7.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3167   -8.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0375   -6.5917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0375   -9.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7542   -3.7042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3250   -9.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7500   -8.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0417   -4.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1792   -6.1792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4667   -9.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1750   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3292   -3.7000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0417   -8.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5375   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8917   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4667   -9.8917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2500   -9.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6042   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6042   -8.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8917   -9.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1750   -7.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1792   -8.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5375   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8917   -7.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2500   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9708  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6833  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6833  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9708  -11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3958  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  7  1  0
  5 14  1  0
  6 25  1  0
  7  2  1  0
  8 10  2  0
  9  1  2  0
 10 13  1  0
 11  5  2  0
 12  6  2  0
 13  4  1  6
 14  3  1  0
  2 15  1  1
 16 13  1  0
 17 21  2  0
 18  5  1  0
 19  6  1  0
 20 17  1  0
 21 24  1  0
 16 22  1  1
 23 20  1  0
 24  8  1  0
 25 26  1  0
 26 28  1  0
 27 30  2  0
 28 16  1  0
 29 27  1  0
 30 21  1  0
 31 23  1  0
 32 31  1  0
 33 34  1  0
 34 35  1  0
 35 32  1  0
 36 33  1  0
 29 20  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3706608

   ---

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: 524.68

Molecular Weight (Monoisotopic): 524.2556

AlogP: 2.99

#Rotatable Bonds: 20

Polar Surface Area: 159.18

Molecular Species: ACID

HBA: 7

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.59

CX Basic pKa: 8.05

CX LogP: 0.59

CX LogD: -2.27

Aromatic Rings: 1

Heavy Atoms: 36

QED Weighted: 0.13

Np Likeness Score: 0.58

References

1. Bernstein PR, Snyder DW, Adams EJ, Krell RD, Vacek EP, Willard AK..  (1986)  Chemically stable homocinnamyl analogues of the leukotrienes: synthesis and preliminary biological evaluation.,  29  (12): [PMID:2878081] [10.1021/jm00162a010]

Source

Source(1):

• Scientific Literature