ID: ALA5285377

Max Phase: Preclinical

Molecular Formula: C21H20N4O3

Molecular Weight: 376.42

Names and Identifiers

Canonical SMILES:  COCc1c(-c2cc(C)on2)ncc2[nH]c3ccc4oc(C(C)C)nc4c3c12

Standard InChI:  InChI=1S/C21H20N4O3/c1-10(2)21-24-20-16(27-21)6-5-13-18(20)17-12(9-26-4)19(22-8-15(17)23-13)14-7-11(3)28-25-14/h5-8,10,23H,9H2,1-4H3

Standard InChI Key:  YJZGQBGGTBIAOP-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    1.6214   -1.3070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8005   -1.3898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3185   -0.7204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6571    0.0316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4779    0.1145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9600   -0.5548    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5050   -0.9766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5050   -1.8217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2966   -2.0735    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2322   -2.2434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9658   -1.8255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9658   -0.9771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2340   -0.5548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2447    0.7460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5800    0.7460    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9924    1.4603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8903    0.8288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4780    1.5431    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0490    2.1616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7832    1.8310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6910    1.0072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5991   -0.3919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2603    0.3599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4165    0.2652    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6727    1.0743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4976    1.0743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2603    1.7886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4976    2.2434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  2  0
  3  4  1  0
  4  5  2  0
  6  5  1  0
  1  6  2  0
  7  3  1  0
  8  7  2  0
  8  9  1  0
  9  2  1  0
 10  8  1  0
 11 10  2  0
 12 11  1  0
 13 12  2  0
  7 13  1  0
  4 14  1  0
 14 15  1  0
 15 16  1  0
  5 17  1  0
 18 17  2  0
 18 19  1  0
 19 20  1  0
 21 20  2  0
 17 21  1  0
 12 22  1  0
 22 23  1  0
 24 23  2  0
 13 24  1  0
 23 25  1  0
 25 26  1  0
 25 27  1  0
 20 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5285377

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 376.42

Molecular Weight (Monoisotopic): 376.1535

AlogP: 5.09

#Rotatable Bonds: 4

Polar Surface Area: 89.97

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.69

CX Basic pKa: 0.69

CX LogP: 3.45

CX LogD: 3.45

Aromatic Rings: 5

Heavy Atoms: 28

QED Weighted: 0.47

Np Likeness Score: -0.61

References

1. Beato A, Gori A, Boucherle B, Peuchmaur M, Haudecoeur R..  (2021)  β-Carboline as a Privileged Scaffold for Multitarget Strategies in Alzheimer's Disease Therapy.,  64  (3.0): [PMID:33528252] [10.1021/acs.jmedchem.0c01887]

Source

Source(1):

• Scientific Literature