2-Hydroxy-3-isobutyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinoline-2-carbonitrile

ID: ALA4860699

PubChem CID: 164616494

Max Phase: Preclinical

Molecular Formula: C20H28N2O3

Molecular Weight: 344.46

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cc2c(cc1OC)C1CC(O)(C#N)C(CC(C)C)CN1CC2

Standard InChI:  InChI=1S/C20H28N2O3/c1-13(2)7-15-11-22-6-5-14-8-18(24-3)19(25-4)9-16(14)17(22)10-20(15,23)12-21/h8-9,13,15,17,23H,5-7,10-11H2,1-4H3

Standard InChI Key:  DGLPXLLFZLJOLW-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   27.5691  -14.1158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1607  -13.4033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7479  -14.1132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.3137  -10.9075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3125  -11.7349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0273  -12.1477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0255  -10.4949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7408  -10.9039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7396  -11.7369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1803  -10.9060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4588  -10.4862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1791  -11.7391    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.4532  -12.1490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4453  -12.9780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8875  -12.9935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8972  -12.1581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5975  -13.4134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3163  -13.0085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0263  -13.4284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3249  -12.1835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5977  -12.1468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.8836  -11.7338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5992  -10.4953    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.5990   -9.6703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9773  -14.8282    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  5  2  0
  5  6  1  0
  6  9  2  0
  8  7  2  0
  7  4  1  0
  8  9  1  0
  8 11  1  0
  9 13  1  0
 12 10  1  0
 10 11  1  0
 12 13  1  0
 12 16  1  0
 13 14  1  0
 14  2  1  0
  2 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
  5 21  1  0
 21 22  1  0
  4 23  1  0
 23 24  1  0
  1 25  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA4860699

   ---

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: 344.46

Molecular Weight (Monoisotopic): 344.2100

AlogP: 2.92

#Rotatable Bonds: 4

Polar Surface Area: 65.72

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.93

CX Basic pKa: 7.20

CX LogP: 2.44

CX LogD: 2.22

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.85

Np Likeness Score: 0.72

References

1. Yang Y, Yu D, Zhu X, Du G, Wang W, Zou F, Wang H, Zhang R, Ye L, Tian J..  (2021)  Synthesis and analysis of dihydrotetrabenazine derivatives as novel vesicular monoamine transporter 2 inhibitors.,  224  [PMID:34329999] [10.1016/j.ejmech.2021.113718]

Source

Source(1):

• Scientific Literature