5-Benzyloxy-2-diphenylacetyl-6-methoxy-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid

ID: ALA155836

Cas Number: 152362-51-1

PubChem CID: 9892451

Max Phase: Preclinical

Molecular Formula: C32H29NO5

Molecular Weight: 507.59

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc2c(c1OCc1ccccc1)CC(C(=O)O)N(C(=O)C(c1ccccc1)c1ccccc1)C2

Standard InChI:  InChI=1S/C32H29NO5/c1-37-28-18-17-25-20-33(31(34)29(23-13-7-3-8-14-23)24-15-9-4-10-16-24)27(32(35)36)19-26(25)30(28)38-21-22-11-5-2-6-12-22/h2-18,27,29H,19-21H2,1H3,(H,35,36)

Standard InChI Key:  GHBCIXGRCZIPNQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 38 42  0  0  0  0  0  0  0  0999 V2000
    6.0000   -2.9167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7042   -3.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0000   -2.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5750   -2.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2792   -3.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8625   -1.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2875   -1.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5667   -2.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7000   -4.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7125   -1.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8625   -0.8500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4167   -2.9250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1542   -2.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8625   -3.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7167   -0.8542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4125   -4.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9792   -4.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1542   -2.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8625   -0.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4250   -2.1042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4375   -1.6792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1500    0.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4042   -5.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2750   -4.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9792   -5.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1167   -4.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7250   -2.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1500    1.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4417   -0.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2667   -5.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8292   -4.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1125   -5.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5542   -4.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7250    0.3833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4375    1.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7167    1.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5542   -5.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8292   -5.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  8  2  0
  5  1  1  0
  6  4  1  0
  7  3  1  0
  8  5  1  0
  9  2  1  0
 10  3  1  0
 11  6  1  0
 12  2  2  0
 13 18  1  0
 14  8  1  0
 15 10  2  0
 16  9  1  0
 17  9  1  0
 18 14  2  0
 19 11  1  0
 20 10  1  0
 21 13  1  0
 22 19  1  0
 23 16  2  0
 24 17  2  0
 25 17  1  0
 26 16  1  0
 27 21  1  0
 28 22  2  0
 29 22  1  0
 30 25  2  0
 31 26  2  0
 32 23  1  0
 33 24  1  0
 34 29  2  0
 35 28  1  0
 36 34  1  0
 37 30  1  0
 38 31  1  0
  7  4  1  0
 13  6  2  0
 37 33  2  0
 38 32  2  0
 36 35  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA155836

   2-(2,2-diphenylacetyl)-6-methoxy-5-phenylmethoxy-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: 507.59

Molecular Weight (Monoisotopic): 507.2046

AlogP: 5.44

#Rotatable Bonds: 8

Polar Surface Area: 76.07

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.70

CX Basic pKa: ┄

CX LogP: 5.79

CX LogD: 2.49

Aromatic Rings: 4

Heavy Atoms: 38

QED Weighted: 0.34

Np Likeness Score: -0.17

References

1. Klutchko S, Hamby JM, Hodges JC.  (1994)  Tetrahydroisoquinoline derivatives with AT2-specific angiotensin II reception binding inhibitory activity,  4  (1): [10.1016/S0960-894X(01)81122-7]

2. Klutchko S, Hamby JM, Hodges JC.  (1994)  Tetrahydroisoquinoline derivatives with AT2-specific angiotensin II reception binding inhibitory activity,  4  (1): [10.1016/S0960-894X(01)81122-7]

3. Juillerat-Jeanneret L..  (2020)  The Other Angiotensin II Receptor: AT2R as a Therapeutic Target.,  63  (5): [PMID:32030982] [10.1021/acs.jmedchem.9b01780]

4. Wannberg J,Gising J,Lindman J,Salander J,Gutiérrez-de-Terán H,Ablahad H,Hamid S,Grönbladh A,Spizzo I,Gaspari TA,Widdop RE,Hallberg A,Backlund M,Leśniak A,Hallberg M,Larhed M.  (2021)  N-(Methyloxycarbonyl)thiophene sulfonamides as high affinity AT2 receptor ligands.,  29  [PMID:33309749] [10.1016/j.bmc.2020.115859]

Source

Source(1):

• Scientific Literature