(E/Z)-4-[4-(2-Benzoylaminoethylcarbamoyl)phenoxy]adamantane-1-carboxylic acid

ID: ALA3613338

PubChem CID: 122188922

Max Phase: Preclinical

Molecular Formula: C27H30N2O5

Molecular Weight: 462.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NCCNC(=O)c1ccc(OC2C3CC4CC2CC(C(=O)O)(C4)C3)cc1)c1ccccc1

Standard InChI:  InChI=1S/C27H30N2O5/c30-24(18-4-2-1-3-5-18)28-10-11-29-25(31)19-6-8-22(9-7-19)34-23-20-12-17-13-21(23)16-27(14-17,15-20)26(32)33/h1-9,17,20-21,23H,10-16H2,(H,28,30)(H,29,31)(H,32,33)

Standard InChI Key:  KIOYUUIZXULWSF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 34 38  0  0  0  0  0  0  0  0999 V2000
    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
    0.1155    2.9863    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
   -1.1714    2.6233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.1284   -0.2145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9912    1.1391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4839    2.2333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6928    0.1656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2987   -1.1346    0.0000 O   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
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   -3.3781   -7.8187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0422   -7.6282    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8237   -9.1130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5711   -9.6671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7896  -11.1519    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1844  -11.7060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4029  -13.1908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1255  -10.9614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7962  -13.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0116  -15.2311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8337  -16.1598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4404  -15.6041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2250  -14.1197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  1  0
  2  4  1  0
  3  5  1  0
  4  6  1  0
  5  6  1  0
  7  8  1  0
  3  7  1  0
  2  9  1  0
  6 10  1  0
 10  8  1  0
  8  9  1  0
  2 11  1  0
 11 12  2  0
 11 13  1  0
 10 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
 18 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  2  0
 28 30  2  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 34 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3613338

   ---

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: 462.55

Molecular Weight (Monoisotopic): 462.2155

AlogP: 3.50

#Rotatable Bonds: 8

Polar Surface Area: 104.73

Molecular Species: ACID

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.05

CX Basic pKa: ┄

CX LogP: 3.43

CX LogD: 0.31

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.52

Np Likeness Score: -0.18

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