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

ID: ALA4861414

PubChem CID: 154634334

Max Phase: Preclinical

Molecular Formula: C20H9FO8

Molecular Weight: 396.28

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(O)c1cc2c(oc1=O)c(-c1ccccc1F)cc1cc(C(=O)O)c(=O)oc12

Standard InChI:  InChI=1S/C20H9FO8/c21-14-4-2-1-3-9(14)10-5-8-6-12(17(22)23)19(26)28-15(8)11-7-13(18(24)25)20(27)29-16(10)11/h1-7H,(H,22,23)(H,24,25)

Standard InChI Key:  UHTOOJSTXDOXGL-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   14.6409  -20.0515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6427  -21.7047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9309  -21.2916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2211  -21.6992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2170  -22.5216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9288  -22.9347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6448  -22.5254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3563  -20.4607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3552  -21.2892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0682  -21.7023    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7870  -21.2913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7881  -20.4627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0706  -20.0451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5010  -22.9315    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5003  -21.7058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5038  -20.0510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2173  -20.4653    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5057  -19.2259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9269  -23.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2110  -24.1735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6401  -24.1782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2150  -20.0547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2146  -19.2285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5000  -18.8176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7853  -19.2317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7898  -20.0610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5049  -20.4683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9287  -18.8153    0.0000 F   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
  6  7  1  0
  7  8  2  0
  9 10  1  0
  9 14  1  0
 10 11  1  0
 11 12  1  0
 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
 24 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4861414

   ---

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: 396.28

Molecular Weight (Monoisotopic): 396.0281

AlogP: 3.10

#Rotatable Bonds: 3

Polar Surface Area: 135.02

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.64

CX Basic pKa: ┄

CX LogP: 2.56

CX LogD: -4.38

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.40

Np Likeness Score: -0.11

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