methyl 6-hydroxy-9H-pyrido[3,4-b]indole-3-carboxylate

ID: ALA5276119

Max Phase: Preclinical

Molecular Formula: C13H10N2O3

Molecular Weight: 242.23

Names and Identifiers

Canonical SMILES:  COC(=O)c1cc2c(cn1)[nH]c1ccc(O)cc12

Standard InChI:  InChI=1S/C13H10N2O3/c1-18-13(17)11-5-9-8-4-7(16)2-3-10(8)15-12(9)6-14-11/h2-6,15-16H,1H3

Standard InChI Key:  UULFOYXSWNADTF-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 18 20  0  0  0  0  0  0  0  0999 V2000
   -1.2281   -0.5732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9427   -0.9855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5163   -0.9851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5163   -1.8103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2264   -2.2221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9427   -1.8140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2665   -2.0562    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2878   -0.7350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7586   -1.3886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6180   -0.0028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4196    0.0782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8895   -0.5710    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5635   -1.3071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8322    0.7928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4196    1.5075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8322    2.2221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6574    0.7928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6574   -0.5729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  1  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  2  6  1  0
  4  7  1  0
  3  8  1  0
  9  8  2  0
  9  7  1  0
  8 10  1  0
 11 10  2  0
 12 11  1  0
 13 12  2  0
  9 13  1  0
 11 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  2  0
  2 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5276119

   ---

Molecule Features

Natural Product: Yes

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: 242.23

Molecular Weight (Monoisotopic): 242.0691

AlogP: 2.21

#Rotatable Bonds: 1

Polar Surface Area: 75.21

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.44

CX Basic pKa: 2.46

CX LogP: 1.76

CX LogD: 1.76

Aromatic Rings: 3

Heavy Atoms: 18

QED Weighted: 0.64

Np Likeness Score: 0.30

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