Methyl 2-[(1S,7aR,12bS)-1-Ethyl-7a-hydroxy-1H,2H,3H,4H,6H,7H,7aH,12bH-indolo[2,3-a]quinolizin-1-yl]acetate

ID: ALA4546064

PubChem CID: 153284538

Max Phase: Preclinical

Molecular Formula: C20H26N2O3

Molecular Weight: 342.44

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC[C@@]1(CC(=O)OC)CCCN2CC[C@]3(O)C(=Nc4ccccc43)[C@@H]21

Standard InChI:  InChI=1S/C20H26N2O3/c1-3-19(13-16(23)25-2)9-6-11-22-12-10-20(24)14-7-4-5-8-15(14)21-17(20)18(19)22/h4-5,7-8,18,24H,3,6,9-13H2,1-2H3/t18-,19+,20-/m1/s1

Standard InChI Key:  YBYNDJLJJQWZRL-HSALFYBXSA-N

Molfile:  

 
     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
    2.1406   -3.6567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1395   -4.4762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8475   -4.8852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8457   -3.2478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5543   -3.6531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5592   -4.4762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3435   -4.7261    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3357   -3.3942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8208   -4.0590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4845   -2.5560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6644   -2.6422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9696   -3.2208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6343   -3.9700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1128   -4.6313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9289   -4.5494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2642   -3.8002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7834   -3.1329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4509   -3.9663    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7779   -5.3767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5169   -5.3365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3341   -5.3392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7404   -6.0482    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7450   -4.6328    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5575   -6.0509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2561   -6.0394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7517   -2.8106    0.0000 O   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
  6  7  1  0
  7  9  2  0
  8  5  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 17  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 13 18  1  6
 14 19  1  0
 14 20  1  1
 20 21  1  0
 21 22  1  0
 21 23  2  0
 22 24  1  0
 19 25  1  0
  8 26  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4546064

   ---

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: 342.44

Molecular Weight (Monoisotopic): 342.1943

AlogP: 2.79

#Rotatable Bonds: 3

Polar Surface Area: 62.13

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.67

CX Basic pKa: 6.83

CX LogP: 2.79

CX LogD: 2.69

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.86

Np Likeness Score: 1.15

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