Aristone

ID: ALA4474412

PubChem CID: 25085910

Max Phase: Preclinical

Molecular Formula: C20H24N2O

Molecular Weight: 308.43

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC1(C)[C@@H]2C[C@@H]3[C@H]4C[C@@]5(Nc6ccccc6[C@@H]5N41)[C@]3(C)CC2=O

Standard InChI:  InChI=1S/C20H24N2O/c1-18(2)13-8-12-15-9-20(19(12,3)10-16(13)23)17(22(15)18)11-6-4-5-7-14(11)21-20/h4-7,12-13,15,17,21H,8-10H2,1-3H3/t12-,13-,15-,17+,19-,20+/m1/s1

Standard InChI Key:  PWDJTEKEZQUXQT-OWZJPITLSA-N

Molfile:  

 
     RDKit          2D

 27 32  0  0  0  0  0  0  0  0999 V2000
   11.7818  -10.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7807  -11.5874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4887  -11.9964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4869  -10.3590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1956  -10.7643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1958  -11.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9784  -10.5098    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.4625  -11.1755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9783  -11.8358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2401  -11.4321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2365  -12.2508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4546  -12.4976    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.2782  -13.2937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8809  -13.8488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6628  -13.6021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8421  -12.8003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4565  -14.4247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5708  -13.1741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2459  -14.2134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4659  -14.5526    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.6941  -13.8675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4837  -13.0751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9394  -11.8369    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.2448  -12.0887    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.3591  -12.9595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5621  -12.5385    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.2448  -15.2140    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  9  1  0
  8  7  1  6
  7  5  1  0
  8  9  1  0
  9 12  1  0
 11 10  1  0
 10  8  1  0
 11 12  1  0
 11 16  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 16 18  1  0
 18 19  1  0
 17 19  1  0
 14 20  1  1
 13 21  1  0
 13 22  1  0
 18  8  1  0
 11 23  1  1
 16 24  1  1
 18 25  1  1
  9 26  1  6
 17 27  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4474412

   (1S,2R,4R,12S,15S,18R)-14,14,18-trimethyl-5,13-diazahexacyclo[13.3.1.02,13.04,12.04,18.06,11]nonadeca-6,8,10-trien-16-one

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: 308.43

Molecular Weight (Monoisotopic): 308.1889

AlogP: 3.37

#Rotatable Bonds: ┄

Polar Surface Area: 32.34

Molecular Species: BASE

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 10.23

CX LogP: 2.45

CX LogD: -0.30

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.80

Np Likeness Score: 1.34

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