Methyl(2S,3R,4S)-1-acetyl-3-(2-methoxy-2-oxoethyl)-2-phenyl-1,2,3,4-tetrahydroquinoline-4-carboxylate

ID: ALA4218877

PubChem CID: 145969185

Max Phase: Preclinical

Molecular Formula: C22H23NO5

Molecular Weight: 381.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)C[C@@H]1[C@H](C(=O)OC)c2ccccc2N(C(C)=O)[C@@H]1c1ccccc1

Standard InChI:  InChI=1S/C22H23NO5/c1-14(24)23-18-12-8-7-11-16(18)20(22(26)28-3)17(13-19(25)27-2)21(23)15-9-5-4-6-10-15/h4-12,17,20-21H,13H2,1-3H3/t17-,20-,21-/m1/s1

Standard InChI Key:  DFFYLNFJCWFCTJ-DUXKGJEZSA-N

Molfile:  

     RDKit          2D

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    8.4302  -16.1392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1446  -16.5518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1428  -14.8997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8579  -15.3087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8612  -16.1413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5800  -16.5523    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.3000  -16.1353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5731  -14.8871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2971  -15.3046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0127  -16.5449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0134  -17.3705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7276  -17.7810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4416  -17.3670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4370  -16.5382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5822  -17.3769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8693  -17.7911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2975  -17.7872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5694  -14.0626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2816  -13.6469    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8534  -13.6536    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8496  -12.8291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0104  -14.8910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7252  -15.3019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4385  -14.8882    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7268  -16.1264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3057  -16.0119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1534  -15.2991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  5  9  1  0
  6  7  1  0
  7  8  1  0
  8 10  1  0
  9 10  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 26  2  0
 26 11  1  0
  8 11  1  1
  7 16  1  0
 16 17  2  0
 16 18  1  0
  9 19  1  1
 19 20  2  0
 19 21  1  0
 21 22  1  0
 10 23  1  1
 23 24  1  0
 24 25  1  0
 24 27  2  0
 25 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4218877

   ---

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: 381.43

Molecular Weight (Monoisotopic): 381.1576

AlogP: 3.23

#Rotatable Bonds: 4

Polar Surface Area: 72.91

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.35

CX LogD: 2.35

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.76

Np Likeness Score: 0.01

References

1. Goli N, Mainkar PS, Kotapalli SS, K T, Ummanni R, Chandrasekhar S..  (2017)  Expanding the tetrahydroquinoline pharmacophore.,  27  (8): [PMID:28318941] [10.1016/j.bmcl.2017.02.077]

Source

Source(1):

• Scientific Literature