2-((1S,3R)-9-methoxy-1-methyl-5,10-dioxo-3,4,5,10-tetrahydro-1H-benzo[g]isochromen-3-yl)acetic acid

ID: ALA4761159

PubChem CID: 102396680

Max Phase: Preclinical

Molecular Formula: C17H16O6

Molecular Weight: 316.31

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cccc2c1C(=O)C1=C(C[C@H](CC(=O)O)O[C@H]1C)C2=O

Standard InChI:  InChI=1S/C17H16O6/c1-8-14-11(6-9(23-8)7-13(18)19)16(20)10-4-3-5-12(22-2)15(10)17(14)21/h3-5,8-9H,6-7H2,1-2H3,(H,18,19)/t8-,9+/m0/s1

Standard InChI Key:  ROSHODBELPZZPV-DTWKUNHWSA-N

Molfile:  

 
     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    9.8668  -15.4399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8656  -16.2595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5737  -16.6684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5719  -15.0311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2805  -15.4363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2794  -16.2570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9856  -16.6660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9879  -15.0247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5695  -14.2139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8605  -13.8074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9879  -14.2075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9833  -17.4832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6986  -15.4383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6952  -16.2570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3985  -16.6670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1098  -16.2629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1132  -15.4442    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4054  -15.0297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4077  -14.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8152  -16.6754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5252  -16.2708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2306  -16.6833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5297  -15.4536    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
  5  8  1  0
  6  7  1  0
  7 14  1  0
 13  8  1  0
  4  9  1  0
  9 10  1  0
  8 11  2  0
  7 12  2  0
 13 14  2  0
 13 18  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  6
 16 20  1  1
 20 21  1  0
 21 22  1  0
 21 23  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4761159

   2-[(1S,3R)-9-methoxy-1-methyl-5,10-dioxo-3,4-dihydro-1H-benzo[g]isochromen-3-yl]acetic acid

Molecule Features

Natural Product: No

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: 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: 3.48

CX Basic pKa: ┄

CX LogP: 1.21

CX LogD: -2.17

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.92

Np Likeness Score: 1.39

References

1. Hu Y,Wang L,Han X,Zhou Y,Zhang T,Wang L,Hong T,Zhang W,Guo XX,Sun J,Qi Y,Yu J,Liu H,Wu F.  (2019)  Discovery of a Bioactive Inhibitor with a New Scaffold for Cystathionine γ-Lyase.,  62  (3): [PMID:30562026] [10.1021/acs.jmedchem.8b01720]

Source

Source(1):

• Scientific Literature