(S)-N-((R)-1-acetyl-6-(quinolin-3-ylmethyl)-1,2,3,4-tetrahydroquinolin-4-yl)-2-amino-3-(4-hydroxy-2,6-dimethylphenyl)propanamide 2,2,2-trifluoroacetate

ID: ALA4550332

PubChem CID: 155555052

Max Phase: Preclinical

Molecular Formula: C34H35F3N4O5

Molecular Weight: 522.65

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(=O)N1CC[C@@H](NC(=O)[C@@H](N)Cc2c(C)cc(O)cc2C)c2cc(Cc3cnc4ccccc4c3)ccc21.O=C(O)C(F)(F)F

Standard InChI:  InChI=1S/C32H34N4O3.C2HF3O2/c1-19-12-25(38)13-20(2)26(19)17-28(33)32(39)35-30-10-11-36(21(3)37)31-9-8-22(16-27(30)31)14-23-15-24-6-4-5-7-29(24)34-18-23;3-2(4,5)1(6)7/h4-9,12-13,15-16,18,28,30,38H,10-11,14,17,33H2,1-3H3,(H,35,39);(H,6,7)/t28-,30+;/m0./s1

Standard InChI Key:  VLZAXVJRRJTXMP-VYVVXECBSA-N

Molfile:  

     RDKit          2D

 46 49  0  0  0  0  0  0  0  0999 V2000
   37.5124  -19.8584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.2201  -19.4498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8047  -19.4498    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   37.5124  -20.6756    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   36.8025  -20.2629    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   38.9278  -19.8584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.2201  -18.6326    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.1898  -18.3703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1886  -19.1898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8967  -19.5988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8949  -17.9614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6035  -18.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6023  -19.1873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3085  -19.5963    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.0204  -19.1893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0216  -18.3687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3108  -17.9551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4819  -17.9618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7743  -18.3706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0666  -17.9604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0721  -19.5948    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.7763  -19.1844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3109  -17.1379    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.0186  -16.7293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0186  -15.9121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.7263  -17.1379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4340  -16.7293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7263  -17.9551    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.1417  -17.1379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1370  -17.9545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.8438  -18.3630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.5525  -17.9544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.5499  -17.1330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.8425  -16.7282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.8386  -15.9110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4280  -18.3609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.2608  -18.3621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.3593  -19.1866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3617  -18.3686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6556  -17.9592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9466  -18.3668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9481  -19.1879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6548  -19.5936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3062  -20.4135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5974  -20.8202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0128  -20.8241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  1  0
  1  4  1  0
  1  5  1  0
  2  6  1  0
  2  7  2  0
  8  9  2  0
  9 10  1  0
 10 13  2  0
 12 11  2  0
 11  8  1  0
 12 13  1  0
 12 17  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
  8 18  1  0
 18 19  1  0
 19 20  2  0
 20 39  1  0
 38 21  1  0
 21 22  2  0
 22 19  1  0
 17 23  1  6
 23 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  1  0
 26 28  1  6
 27 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 34 29  1  0
 34 35  1  0
 30 36  1  0
 32 37  1  0
 38 39  1  0
 39 40  2  0
 40 41  1  0
 41 42  2  0
 42 43  1  0
 43 38  2  0
 14 44  1  0
 44 45  1  0
 44 46  2  0
M  END

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 522.65

Molecular Weight (Monoisotopic): 522.2631

AlogP: 4.63

#Rotatable Bonds: 6

Polar Surface Area: 108.55

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.76

CX Basic pKa: 8.05

CX LogP: 4.12

CX LogD: 3.50

Aromatic Rings: 4

Heavy Atoms: 39

QED Weighted: 0.34

Np Likeness Score: -0.17

References

1. Nastase AF, Anand JP, Bender AM, Montgomery D, Griggs NW, Fernandez TJ, Jutkiewicz EM, Traynor JR, Mosberg HI..  (2019)  Dual Pharmacophores Explored via Structure-Activity Relationship (SAR) Matrix: Insights into Potent, Bifunctional Opioid Ligand Design.,  62  (8): [PMID:30916966] [10.1021/acs.jmedchem.9b00378]

Source

Source(1):

• Scientific Literature