6-(4-Methoxypheny0-2,2-dioxo-2,8-dihydropyrano[2,3-f]-chromene-3,9-dicarboxylic Acid

ID: ALA4856506

PubChem CID: 154634332

Max Phase: Preclinical

Molecular Formula: C21H12O9

Molecular Weight: 408.32

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc(-c2cc3cc(C(=O)O)c(=O)oc3c3cc(C(=O)O)c(=O)oc23)cc1

Standard InChI:  InChI=1S/C21H12O9/c1-28-11-4-2-9(3-5-11)12-6-10-7-14(18(22)23)20(26)29-16(10)13-8-15(19(24)25)21(27)30-17(12)13/h2-8H,1H3,(H,22,23)(H,24,25)

Standard InChI Key:  CNONOFMPWKREIC-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   14.5406  -13.8964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   13.8305  -15.1364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1208  -15.5440    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1167  -16.3664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8285  -16.7795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5444  -16.3703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2560  -14.3056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2548  -15.1341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9678  -15.5471    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6865  -15.1361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6877  -14.3076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9701  -13.8901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4007  -16.7764    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3999  -15.5507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4032  -13.8959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1167  -14.3102    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4053  -13.0709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8266  -17.6081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1106  -18.0183    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5396  -18.0230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1146  -13.8996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1142  -13.0735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3997  -12.6626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6850  -13.0766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6894  -13.9059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4045  -14.3132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9691  -12.6665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9663  -11.8415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  2  0
  3 10  2  0
  9  2  2  0
  2  1  1  0
  3  4  1  0
  3  8  1  0
  4  5  1  0
  5  6  1  0
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  7  8  2  0
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  9 14  1  0
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 12 13  1  0
 13 14  2  0
  6 15  2  0
 12 16  2  0
 17 18  1  0
 17 19  2  0
 13 17  1  0
 20 21  1  0
 20 22  2  0
  7 20  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
  1 23  1  0
 26 29  1  0
 29 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4856506

   ---

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: 408.32

Molecular Weight (Monoisotopic): 408.0481

AlogP: 2.97

#Rotatable Bonds: 4

Polar Surface Area: 144.25

Molecular Species: ACID

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.45

CX Basic pKa: ┄

CX LogP: 2.26

CX LogD: -4.72

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.38

Np Likeness Score: 0.16

References

1. Wei L, Hou T, Li J, Zhang X, Zhou H, Wang Z, Cheng J, Xiang K, Wang J, Zhao Y, Liang X..  (2021)  Structure-Activity Relationship Studies of Coumarin-like Diacid Derivatives as Human G Protein-Coupled Receptor-35 (hGPR35) Agonists and a Consequent New Design Principle.,  64  (5.0): [PMID:33630609] [10.1021/acs.jmedchem.0c01624]

Source

Source(1):

• Scientific Literature