Aristoteline

ID: ALA4463817

PubChem CID: 11098414

Max Phase: Preclinical

Molecular Formula: C20H26N2

Molecular Weight: 294.44

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC1(C)N[C@@H]2Cc3c([nH]c4ccccc34)[C@]3(C)CC[C@H]1C[C@H]23

Standard InChI:  InChI=1S/C20H26N2/c1-19(2)12-8-9-20(3)15(10-12)17(22-19)11-14-13-6-4-5-7-16(13)21-18(14)20/h4-7,12,15,17,21-22H,8-11H2,1-3H3/t12-,15+,17+,20+/m0/s1

Standard InChI Key:  QYBCOSRUKXCALD-GHHTXBMSSA-N

Molfile:  

 
     RDKit          2D

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    8.8689   -8.1760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8689   -6.5499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5701   -6.9626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5666   -7.7757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2645   -8.1809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9746   -7.7817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9780   -6.9686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2715   -6.5548    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1678   -7.7757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1633   -6.9627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3962   -8.0283    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9163   -7.3741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3911   -6.7176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0584   -5.9787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2511   -5.8951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7776   -6.5564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1130   -7.2927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6784   -8.1760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4667   -8.5846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6759   -8.1843    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5587   -8.5846    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5628   -6.1496    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8612   -8.9891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6838   -6.5638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9702   -6.1537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 10  2  1  0
  9  1  1  0
  1  4  1  0
  3  2  1  0
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  3  8  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  9 10  2  0
 10 13  1  0
 12 11  1  0
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 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
  1 18  1  0
 18 19  1  0
  6 19  1  0
  6 20  1  6
  4 21  1  6
  3 22  1  6
  1 23  1  6
  7 24  1  0
  7 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4463817

   (1R,12R,15S,17S)-1,14,14-trimethyl-3,13-diazapentacyclo[13.2.2.02,10.04,9.012,17]nonadeca-2(10),4,6,8-tetraene

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: 294.44

Molecular Weight (Monoisotopic): 294.2096

AlogP: 4.15

#Rotatable Bonds: ┄

Polar Surface Area: 27.82

Molecular Species: BASE

HBA: 1

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 10.70

CX LogP: 3.90

CX LogD: 0.94

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.75

Np Likeness Score: 1.07

References

1. Arias HR, Ortells MO, Feuerbach D, Burgos V, Paz C..  (2019)  Alkaloids Purified from Aristotelia chilensis Inhibit the Human α3β4 Nicotinic Acetylcholine Receptor with Higher Potencies Compared with the Human α4β2 and α7 Subtypes.,  82  (7): [PMID:31276409] [10.1021/acs.jnatprod.9b00314]

Source

Source(1):

• Scientific Literature