2-[(1R,3R)-7-methoxy-1-methyl-5,10-dioxo-3,4-dihydro-1H-benzo[g]isochromen-3-yl]acetic acid

ID: ALA5266877

Max Phase: Preclinical

Molecular Formula: C17H16O6

Molecular Weight: 316.31

Names and Identifiers

Canonical SMILES:  COc1ccc2c(c1)C(=O)C1=C(C2=O)[C@@H](C)O[C@@H](CC(=O)O)C1

Standard InChI:  InChI=1S/C17H16O6/c1-8-15-13(6-10(23-8)7-14(18)19)16(20)12-5-9(22-2)3-4-11(12)17(15)21/h3-5,8,10H,6-7H2,1-2H3,(H,18,19)/t8-,10-/m1/s1

Standard InChI Key:  KHLURFHLJXJMLO-PSASIEDQSA-N

Molfile:  

 
     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   -2.8571    0.4140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1425    0.8263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4306    0.4144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4306   -0.4107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1407   -0.8224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8571   -0.4144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7160    0.8270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0013    0.4143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0013   -0.4107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7160   -0.8233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7132    0.8269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4278    0.4143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4278   -0.4108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7132   -0.8234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7160    1.6521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7160   -1.6485    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7132    1.6521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1425   -0.8234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8571   -0.4108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5717   -0.8234    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8571    0.4143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5717   -0.8270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5717   -1.6521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  1  6  1  0
  6  5  2  0
  3  7  1  0
  8  7  1  0
  9  8  2  0
 10  9  1  0
  4 10  1  0
  8 11  1  0
 12 11  1  0
 13 12  1  0
 14 13  1  0
  9 14  1  0
  7 15  2  0
 10 16  2  0
 11 17  1  1
 13 18  1  1
 18 19  1  0
 19 20  1  0
 19 21  2  0
  6 22  1  0
 22 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5266877

   ---

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: 316.31

Molecular Weight (Monoisotopic): 316.0947

AlogP: 2.02

#Rotatable Bonds: 3

Polar Surface Area: 89.90

Molecular Species: ACID

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.46

CX Basic pKa: ┄

CX LogP: 1.21

CX LogD: -2.18

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.92

Np Likeness Score: 1.19

References

1. Singh R, Salunke DB..  (2021)  Diverse chemical space of indoleamine-2,3-dioxygenase 1 (Ido1) inhibitors.,  211  [PMID:33341650] [10.1016/j.ejmech.2020.113071]

Source

Source(1):

• Scientific Literature