(E/Z)-[5-(4-{2-[(naphthalene-2-carbonyl)amino]ethylcarbamoyl}phenoxy)adamantan-2-yl]acetic acid

ID: ALA3613343

PubChem CID: 122188927

Max Phase: Preclinical

Molecular Formula: C32H34N2O5

Molecular Weight: 526.63

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)CC1C2CC3CC1CC(Oc1ccc(C(=O)NCCNC(=O)c4ccc5ccccc5c4)cc1)(C3)C2

Standard InChI:  InChI=1S/C32H34N2O5/c35-29(36)16-28-25-13-20-14-26(28)19-32(17-20,18-25)39-27-9-7-22(8-10-27)30(37)33-11-12-34-31(38)24-6-5-21-3-1-2-4-23(21)15-24/h1-10,15,20,25-26,28H,11-14,16-19H2,(H,33,37)(H,34,38)(H,35,36)

Standard InChI Key:  VQKUNGNAWOVCCL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 39 44  0  0  0  0  0  0  0  0999 V2000
    5.7129    4.0299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5179    2.5244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5179    0.9899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8516   17.4235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1714    0.9899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7356   15.8936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9912    1.1391    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0235   13.0032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7572   15.5877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5639    7.8314    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1155    2.9863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8341    5.2455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9743   18.6369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9734    1.9964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9045   11.7882    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5445   -0.2145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3420    5.0922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6074    2.5076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2987   -1.1346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1714    2.6233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2248   16.0465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4449    6.6164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8583   17.1069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6384    6.7411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7286    3.7233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0996    2.6610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4703   18.4732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2937   10.4173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1747    9.2023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3691   16.9540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1237   14.5273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1284   -0.2145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8299   12.8785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6343   14.3741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3300    0.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9239    0.3135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0862   -2.6203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9724   -3.0667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0296   -3.3620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 21  4  1  0
 23  6  1  0
 17 25  1  0
 30  9  2  0
  2  3  1  0
  1 12  1  0
 23 30  1  0
  8 15  1  0
  3 35  1  0
 22 12  1  0
 18  7  1  0
 18 26  1  0
 20  5  1  0
 27 23  2  0
 11  2  1  0
 14 36  1  0
  5 32  1  0
 13 27  1  0
 11 20  1  0
 32 19  1  0
 35  5  1  0
  3  7  1  0
 15 28  1  0
 34  8  1  0
 22 24  2  0
 25 18  2  0
  4 13  2  0
 14 11  1  0
  6 21  2  0
  8 33  2  0
 12 17  2  0
 10 22  1  0
 28 29  1  0
 16  3  1  0
 31  6  1  0
 36 16  1  0
  9 34  1  0
 29 10  1  0
 34 31  2  0
 26  1  2  0
 36 32  1  0
 19 37  1  0
 37 38  1  0
 37 39  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3613343

   ---

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: 526.63

Molecular Weight (Monoisotopic): 526.2468

AlogP: 5.05

#Rotatable Bonds: 9

Polar Surface Area: 104.73

Molecular Species: ACID

HBA: 4

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 4.15

CX Basic pKa: ┄

CX LogP: 4.26

CX LogD: 1.19

Aromatic Rings: 3

Heavy Atoms: 39

QED Weighted: 0.34

Np Likeness Score: -0.06

References

1. Pagire SH, Pagire HS, Lee GB, Han SJ, Kwak HJ, Kim JY, Kim KY, Rhee SD, Ryu JI, Song JS, Bae MA, Park MJ, Kim D, Lee DH, Ahn JH..  (2015)  Discovery and optimization of adamantane carboxylic acid derivatives as potent diacylglycerol acyltransferase 1 inhibitors for the potential treatment of obesity and diabetes.,  101  [PMID:26218650] [10.1016/j.ejmech.2015.06.043]

Source

Source(1):

• Scientific Literature