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

ID: ALA4878979

PubChem CID: 154634314

Max Phase: Preclinical

Molecular Formula: C21H12O9

Molecular Weight: 408.32

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccccc1-c1cc2cc(C(=O)O)c(=O)oc2c2cc(C(=O)O)c(=O)oc12

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

Standard InChI Key:  CMQPAVILLUFNAX-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   13.5813   -1.3372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2864   -0.9283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2882   -2.5657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5832   -2.1565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8802   -2.5602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8761   -3.3748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5811   -3.7839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2902   -3.3786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9950   -1.3336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9939   -2.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7001   -2.5633    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4119   -2.1562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4131   -1.3356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7024   -0.9220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1669   -3.7808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1185   -2.5668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1219   -0.9278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8286   -1.3381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1238   -0.1106    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5792   -4.6047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8702   -5.0109    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2856   -5.0156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8741   -0.9315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8737   -0.1132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1660    0.3005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4581   -0.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4625   -0.9378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1708   -1.3411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5810    0.2982    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2891   -0.1117    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
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  3  4  1  0
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 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
 29 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4878979

   ---

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: 2.40

CX Basic pKa: ┄

CX LogP: 2.26

CX LogD: -4.73

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.38

Np Likeness Score: 0.21

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]

2. Wei L, Xiang K, Kang H, Yu Y, Fan H, Zhou H, Hou T, Ge Y, Wang J, Guo Z, Chen Y, Zhao Y, Liang X..  (2023)  Development and Characterization of Fluorescent Probes for the G Protein-Coupled Receptor 35.,  14  (4): [PMID:37077394] [10.1021/acsmedchemlett.2c00461]

Source

Source(1):

• Scientific Literature