2-[(1S,12bS)-1-Ethyl-1H,2H,3H,4H,6H,7H,12H,12bH-indolo[2,3-a]quinolizin-1-yl]-N-cyclopentylacetamide

ID: ALA4529035

PubChem CID: 153284543

Max Phase: Preclinical

Molecular Formula: C24H33N3O

Molecular Weight: 379.55

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC[C@@]1(CC(=O)NC2CCCC2)CCCN2CCc3c([nH]c4ccccc34)[C@@H]21

Standard InChI:  InChI=1S/C24H33N3O/c1-2-24(16-21(28)25-17-8-3-4-9-17)13-7-14-27-15-12-19-18-10-5-6-11-20(18)26-22(19)23(24)27/h5-6,10-11,17,23,26H,2-4,7-9,12-16H2,1H3,(H,25,28)/t23-,24+/m1/s1

Standard InChI Key:  VYDBOIQAMVARDZ-RPWUZVMVSA-N

Molfile:  

 
     RDKit          2D

 29 33  0  0  0  0  0  0  0  0999 V2000
   14.9195   -5.5745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9236   -4.7495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2072   -5.1585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9268   -3.7538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9256   -4.5811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6403   -4.9939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6385   -3.3410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3538   -3.7502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3541   -4.5765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1401   -4.8317    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.1397   -3.4946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6262   -4.1672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3019   -2.6541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4744   -2.7376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7884   -3.3266    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.4444   -4.0817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7492   -4.6761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0932   -3.9211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6117   -3.2432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2030   -5.9833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6318   -5.9906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6276   -6.8155    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.3483   -5.5817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3399   -7.2315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4249   -8.0477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2310   -8.2233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6471   -7.5109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0981   -6.8953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0238   -4.7912    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  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
  9 10  1  0
 10 12  1  0
 11  8  1  0
 11 12  2  0
 11 14  1  0
 12 16  1  0
 15 13  1  0
 13 14  1  0
 15 16  1  0
 15 19  1  0
 16  2  1  0
  2 17  1  0
 17 18  1  0
 18 19  1  0
  3 20  1  0
  1 21  1  0
 21 22  1  0
 21 23  2  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 24  1  0
 16 29  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA4529035

   ---

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: 379.55

Molecular Weight (Monoisotopic): 379.2624

AlogP: 4.71

#Rotatable Bonds: 4

Polar Surface Area: 48.13

Molecular Species: NEUTRAL

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.20

CX LogP: 3.97

CX LogD: 3.76

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.81

Np Likeness Score: 0.10

References

1. Norwood VM, Brice-Tutt AC, Eans SO, Stacy HM, Shi G, Ratnayake R, Rocca JR, Abboud KA, Li C, Luesch H, McLaughlin JP, Huigens RW..  (2020)  Preventing Morphine-Seeking Behavior through the Re-Engineering of Vincamine's Biological Activity.,  63  (10): [PMID:31913038] [10.1021/acs.jmedchem.9b01924]

Source

Source(1):

• Scientific Literature