(+/-)-2,3,10-Trimethoxy-5,8,13,13a-tetrahydro-6H-isoquinolino[3,2-a]isoquinolin-11-ol

ID: ALA4521450

PubChem CID: 9549058

Max Phase: Preclinical

Molecular Formula: C20H23NO4

Molecular Weight: 341.41

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cc2c(cc1O)CC1c3cc(OC)c(OC)cc3CCN1C2

Standard InChI:  InChI=1S/C20H23NO4/c1-23-18-9-14-11-21-5-4-12-8-19(24-2)20(25-3)10-15(12)16(21)6-13(14)7-17(18)22/h7-10,16,22H,4-6,11H2,1-3H3

Standard InChI Key:  ZMCOANUSZBGLSK-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   25.2549  -12.2323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2531  -10.5876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9649  -10.9947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9637  -11.8236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3972  -10.9968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6794  -10.5790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3960  -11.8256    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.6737  -12.2335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6659  -13.0585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1105  -12.2427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1009  -13.0737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3787  -13.4777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3683  -14.3034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0797  -14.7261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8027  -14.3170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8094  -13.4927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5100  -14.7334    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.5031  -15.5543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5438  -11.8215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5450  -11.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8333  -10.5922    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.8325  -12.2313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.8318  -13.0522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1233  -11.0040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0708  -15.5468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 19  1  1  0
  1  4  2  0
  3  2  2  0
  2 20  1  0
  3  4  1  0
  3  6  1  0
  4  8  1  0
  7  5  1  0
  5  6  1  0
  7  8  1  0
  7 10  1  0
  8  9  1  0
  9 12  1  0
 11 10  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
 15 17  1  0
 17 18  1  0
 19 20  2  0
 20 21  1  0
 19 22  1  0
 22 23  1  0
 21 24  1  0
 14 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4521450

   2,3,10-trimethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinolin-11-ol

Molecule Features

Natural Product: Yes

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: 341.41

Molecular Weight (Monoisotopic): 341.1627

AlogP: 3.07

#Rotatable Bonds: 3

Polar Surface Area: 51.16

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.97

CX Basic pKa: 5.49

CX LogP: 3.00

CX LogD: 3.00

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.93

Np Likeness Score: 0.92

References

1. Ge H, Zhang Y, Yang Z, Qiang K, Chen C, Sun L, Chen M, Zhang J..  (2019)  Chemical synthesis, microbial transformation and biological evaluation of tetrahydroprotoberberines as dopamine D1/D2 receptor ligands.,  27  (10): [PMID:30981605] [10.1016/j.bmc.2019.04.014]

Source

Source(1):

• Scientific Literature