2,8-Dioxo-6-phenyl-2,8-dihydropyrano[2,3-f]chromene-3,9-dicarboxylic Acid

ID: ALA4856069

PubChem CID: 154634328

Max Phase: Preclinical

Molecular Formula: C20H10O8

Molecular Weight: 378.29

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(O)c1cc2c(oc1=O)c(-c1ccccc1)cc1cc(C(=O)O)c(=O)oc12

Standard InChI:  InChI=1S/C20H10O8/c21-17(22)13-7-10-6-11(9-4-2-1-3-5-9)16-12(15(10)27-19(13)25)8-14(18(23)24)20(26)28-16/h1-8H,(H,21,22)(H,23,24)

Standard InChI Key:  UMNLBGZBVHTJDM-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    4.1217  -18.0979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8268  -17.6890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8286  -19.3264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1236  -18.9172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4206  -19.3209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4165  -20.1354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1215  -20.5446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8306  -20.1393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5354  -18.0943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5343  -18.9149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2405  -19.3240    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9523  -18.9169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9535  -18.0963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2428  -17.6827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7073  -20.5414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6589  -19.3275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6622  -17.6885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3690  -18.0988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6642  -16.8713    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1196  -21.3653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4105  -21.7716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8260  -21.7763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4144  -17.6922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4141  -16.8739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7063  -16.4669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9985  -16.8770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0029  -17.6984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7112  -18.1018    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
  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
M  END

Alternative Forms

1. Parent:

   

   ALA4856069

   ---

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: 378.29

Molecular Weight (Monoisotopic): 378.0376

AlogP: 2.96

#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: 2.56

CX Basic pKa: ┄

CX LogP: 2.42

CX LogD: -4.54

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.41

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