ID: ALA5271392

Max Phase: Preclinical

Molecular Formula: C22H24N2O4

Molecular Weight: 380.44

Names and Identifiers

Canonical SMILES:  COCc1c(C(=O)OC(C)C)ncc2[nH]c3ccc4oc(C(C)C)cc4c3c12

Standard InChI:  InChI=1S/C22H24N2O4/c1-11(2)18-8-13-17(28-18)7-6-15-19(13)20-14(10-26-5)21(22(25)27-12(3)4)23-9-16(20)24-15/h6-9,11-12,24H,10H2,1-5H3

Standard InChI Key:  JFGUJXZLJIUVPZ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
    1.3940   -1.3140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5731   -1.3969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0910   -0.7274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4297    0.0246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2505    0.1075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7326   -0.5619    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7324   -0.9836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7324   -1.8287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0692   -2.0805    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4596   -2.2504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1932   -1.8325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1932   -0.9841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4614   -0.5619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0173    0.7390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8074    0.7390    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2199    1.4533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6629    0.8218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2505    1.5361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4877    0.8218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9001    1.5361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7250    1.5361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4877    2.2504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8265   -0.3989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4877    0.3529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6439    0.2582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9001    1.0673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7250    1.0673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4877    1.7816    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
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 12 23  1  0
 23 24  1  0
 25 24  2  0
 13 25  1  0
 24 26  1  0
 26 27  1  0
 26 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5271392

   ---

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: 380.44

Molecular Weight (Monoisotopic): 380.1736

AlogP: 5.30

#Rotatable Bonds: 5

Polar Surface Area: 77.35

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.31

CX Basic pKa: 1.75

CX LogP: 3.96

CX LogD: 3.96

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.48

Np Likeness Score: 0.13

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