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

ID: ALA4859764

PubChem CID: 154634337

Max Phase: Preclinical

Molecular Formula: C21H12O9

Molecular Weight: 408.32

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cccc(-c2cc3cc(C(=O)O)c(=O)oc3c3cc(C(=O)O)c(=O)oc23)c1

Standard InChI:  InChI=1S/C21H12O9/c1-28-11-4-2-3-9(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:  GMSQXARDKZODQS-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   15.7228   -8.2955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   15.0129   -9.5354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3032   -9.9430    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2991  -10.7653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0108  -11.1783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7267  -10.7692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4382   -8.7046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4371   -9.5331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1500   -9.9461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   17.1524   -8.2891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5831  -11.1752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5820   -9.9496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5853   -8.2950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2989   -8.7092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   15.0089  -12.0069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2930  -12.4171    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7220  -12.4218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2969   -8.2987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2966   -7.4726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5821   -7.0617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8675   -7.4757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8720   -8.3050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5870   -8.7122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5808   -6.2367    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2946   -5.8231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 13 14  2  0
  6 15  2  0
 12 16  2  0
 17 18  1  0
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 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
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 27 28  2  0
 28 23  1  0
  1 23  1  0
 25 29  1  0
 29 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4859764

   ---

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: 2.39

CX Basic pKa: ┄

CX LogP: 2.26

CX LogD: -4.73

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.38

Np Likeness Score: 0.09

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