2-((S)-2-amino-3-(4-hydroxyphenyl)propanoyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

ID: ALA4166622

PubChem CID: 10664865

Max Phase: Preclinical

Molecular Formula: C19H20N2O4

Molecular Weight: 340.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N[C@@H](Cc1ccc(O)cc1)C(=O)N1Cc2ccccc2CC1C(=O)O

Standard InChI:  InChI=1S/C19H20N2O4/c20-16(9-12-5-7-15(22)8-6-12)18(23)21-11-14-4-2-1-3-13(14)10-17(21)19(24)25/h1-8,16-17,22H,9-11,20H2,(H,24,25)/t16-,17?/m0/s1

Standard InChI Key:  VUOZTGVYOFFWCN-BHWOMJMDSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   25.2340  -21.6534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2329  -22.4807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9482  -22.8916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6652  -22.4803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6623  -21.6498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9464  -21.2386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5174  -22.8907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.3717  -21.2325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0882  -21.6444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8017  -21.2272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0913  -22.4695    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.5183  -21.6391    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.7987  -20.4021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.5191  -22.4626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9463  -21.6347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2293  -21.2184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9475  -22.4606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2334  -22.8657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2303  -23.6852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9404  -24.1008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6551  -23.6866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6548  -22.8684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2259  -20.3934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9393  -19.9799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.5092  -19.9859    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  2  7  1  0
  5  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  1
 10 12  1  0
 10 13  2  0
 12 14  1  0
 12 16  1  0
 14 18  1  0
 17 15  1  0
 15 16  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
 16 23  1  0
 23 24  1  0
 23 25  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4166622

   2-[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]-3,4-dihydro-1H-isoquinoline-3-carboxylic 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: 340.38

Molecular Weight (Monoisotopic): 340.1423

AlogP: 1.30

#Rotatable Bonds: 4

Polar Surface Area: 103.86

Molecular Species: ACID

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.55

CX Basic pKa: 8.01

CX LogP: -0.40

CX LogD: -0.48

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.78

Np Likeness Score: 0.01

References

1. Olson KM, Keresztes A, Tashiro JK, Daconta LV, Hruby VJ, Streicher JM..  (2018)  Synthesis and Evaluation of a Novel Bivalent Selective Antagonist for the Mu-Delta Opioid Receptor Heterodimer that Reduces Morphine Withdrawal in Mice.,  61  (14): [PMID:29939746] [10.1021/acs.jmedchem.8b00403]

Source

Source(1):

• Scientific Literature