(1,2-cis-2,3-cis-3,4-cis)-1,3-Bis(4-(2-benzyloxy)-acetamidobenzamido)-2,4-bis(3-methoxy-4-(thiophene-2-carbonyloxy)phenyl)cyclobutane-1,3-dicarboxylic acid

ID: ALA2158491

PubChem CID: 56945740

Max Phase: Preclinical

Molecular Formula: C62H52N4O16S2

Molecular Weight: 1173.24

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc([C@H]2[C@](NC(=O)c3ccc(NC(=O)COCc4ccccc4)cc3)(C(=O)O)[C@@H](c3ccc(OC(=O)c4cccs4)c(OC)c3)[C@]2(NC(=O)c2ccc(NC(=O)COCc3ccccc3)cc2)C(=O)O)ccc1OC(=O)c1cccs1

Standard InChI:  InChI=1S/C62H52N4O16S2/c1-77-47-31-41(21-27-45(47)81-57(71)49-15-9-29-83-49)53-61(59(73)74,65-55(69)39-17-23-43(24-18-39)63-51(67)35-79-33-37-11-5-3-6-12-37)54(42-22-28-46(48(32-42)78-2)82-58(72)50-16-10-30-84-50)62(53,60(75)76)66-56(70)40-19-25-44(26-20-40)64-52(68)36-80-34-38-13-7-4-8-14-38/h3-32,53-54H,33-36H2,1-2H3,(H,63,67)(H,64,68)(H,65,69)(H,66,70)(H,73,74)(H,75,76)/t53-,54+,61+,62-

Standard InChI Key:  GWXCJNSAPLTMEP-AXEJPZLSSA-N

Molfile:  

     RDKit          2D

 84 92  0  0  0  0  0  0  0  0999 V2000
   14.1346   -4.4637    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.1281   -5.2886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8393   -5.7068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8291   -6.5298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5395   -6.9478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2582   -6.5409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2621   -5.7116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5511   -5.2973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9699   -6.9581    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.9645   -7.7831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6763   -8.2002    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4104   -5.6955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7349   -3.0431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7375   -3.8666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5617   -3.8673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5625   -3.0416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2688   -2.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3234   -2.3283    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9085   -3.0434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7355   -1.6136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5605   -1.6132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3226   -0.8994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7370   -0.1882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3248    0.5256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4989    0.5256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0870   -0.1942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5015   -0.9050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9861   -3.0194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6930   -2.5957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6796   -1.7699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9533   -1.3697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2493   -1.7958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4142   -2.9964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3865   -1.3445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3715   -0.5196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0401   -0.0358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6496   -0.1201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8246   -0.2907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3107    0.3759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8269    1.0442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0419    0.7907    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.0851    1.2393    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.4963    1.9545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0824    2.6682    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4958   -2.3290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4962   -3.7579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3119   -4.5615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4835   -4.5457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0536   -5.2490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4485   -5.9744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2775   -5.9921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7002   -5.2839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2289   -5.2283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8345   -4.5037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0194   -6.6790    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4152   -7.4029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9093   -8.0552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2400   -7.4221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0812   -8.0314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8018   -8.8077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4538   -9.3132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1361   -8.8495    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   17.1218   -2.5723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3833   -3.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7964   -4.5808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6620   -3.2977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3212    1.9560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7324    2.6713    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5574    2.6728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9686    3.3880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7952    3.3849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2063    4.1007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7924    4.8194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9632    4.8152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5558    4.0969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2473   -8.1909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2419   -9.0159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5248   -9.4237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5194  -10.2486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8010  -10.6508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7952  -11.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5075  -11.8931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2271  -11.4808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2293  -10.6580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 39 40  2  0
 41 36  1  0
  9 10  1  0
 25 42  1  0
 20 21  2  0
 42 43  1  0
  2  3  1  0
 43 44  2  0
 20 22  1  0
 19 45  1  0
 10 11  2  0
 19 46  2  0
 22 23  2  0
 14 47  1  1
  5  6  2  0
 47 48  2  0
 23 24  1  0
 48 49  1  0
  2 12  2  0
 49 50  2  0
 24 25  2  0
 50 51  1  0
 13 14  1  0
 51 52  2  0
 52 47  1  0
 25 26  1  0
 49 53  1  0
  1  2  1  0
 53 54  1  0
 26 27  2  0
 50 55  1  0
 27 22  1  0
 55 56  1  0
  6  7  1  0
 56 57  1  0
 17 28  2  0
 56 58  2  0
 61 62  1  0
  3  4  2  0
 59 60  1  0
 28 29  1  0
  7  8  2  0
 29 30  2  0
 57 59  2  0
 60 61  2  0
 62 57  1  0
 15  1  1  1
 14 15  1  0
 33 63  1  0
 30 31  1  0
 15 64  1  0
 15 16  1  0
 64 65  1  0
 31 32  2  0
 64 66  2  0
 32 17  1  0
 43 67  1  0
 16 13  1  0
 67 68  1  0
 29 33  1  0
 68 69  1  0
  8  3  1  0
 69 70  1  0
 30 34  1  0
 70 71  2  0
 16 17  1  1
 71 72  1  0
 34 35  1  0
 72 73  2  0
 73 74  1  0
 35 36  1  0
 74 75  2  0
 75 70  1  0
 13 18  1  1
 10 76  1  0
 35 37  2  0
 76 77  1  0
 40 41  1  0
 77 78  1  0
  6  9  1  0
 78 79  1  0
 38 39  1  0
 79 80  2  0
 13 19  1  0
 80 81  1  0
  4  5  1  0
 81 82  2  0
 18 20  1  0
 82 83  1  0
 36 38  2  0
 83 84  2  0
 84 79  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2158491

   2,4-Bis[3-methoxy-4-(thiophene-2-carbonyloxy)phenyl]-1,3-bis[[4-[(2-phenylmethoxyacetyl)amino]benzoyl]amino]cyclobutane-1,3-dicarboxylic 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: 1173.24

Molecular Weight (Monoisotopic): 1172.2820

AlogP: ┄

#Rotatable Bonds: ┄

Polar Surface Area: ┄

Molecular Species: ┄

HBA: ┄

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): ┄

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: ┄

CX LogD: ┄

Aromatic Rings: ┄

Heavy Atoms: ┄

QED Weighted: ┄

Np Likeness Score: ┄

References

1. Liu Q, Li N, Yuan Y, Lu H, Wu X, Zhou C, He M, Su H, Zhang M, Wang J, Wang B, Wang Y, Ma D, Ye Y, Weiss HC, Gesing ER, Liao J, Wang MW..  (2012)  Cyclobutane derivatives as novel nonpeptidic small molecule agonists of glucagon-like peptide-1 receptor.,  55  (1): [PMID:22103243] [10.1021/jm201150j]

Source

Source(1):

• Scientific Literature