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

ID: ALA4848109

PubChem CID: 154634331

Max Phase: Preclinical

Molecular Formula: C23H16O8

Molecular Weight: 420.37

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)c1ccc(-c2cc3cc(C(=O)O)c(=O)oc3c3cc(C(=O)O)c(=O)oc23)cc1

Standard InChI:  InChI=1S/C23H16O8/c1-10(2)11-3-5-12(6-4-11)14-7-13-8-16(20(24)25)22(28)30-18(13)15-9-17(21(26)27)23(29)31-19(14)15/h3-10H,1-2H3,(H,24,25)(H,26,27)

Standard InChI Key:  AOYPPKYSYHPZRI-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
   23.6492  -18.0421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3610  -17.6293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3628  -19.2824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6511  -18.8693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9415  -19.2769    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.9373  -20.0992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6491  -20.5123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3650  -20.1031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0765  -18.0385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0753  -18.8670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7883  -19.2800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.5070  -18.8690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5081  -18.0405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7906  -17.6230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2213  -20.5092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.2203  -19.2835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.2237  -17.6288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9372  -18.0431    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.2257  -16.8038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.6470  -21.3409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9313  -21.7511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.3602  -21.7558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.9352  -17.6326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9348  -16.8064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2203  -16.3955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5057  -16.8096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5101  -17.6388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2252  -18.0461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7898  -16.3995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7870  -15.5745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0768  -16.8145    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
 26 29  1  0
 29 30  1  0
 29 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4848109

   ---

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: 420.37

Molecular Weight (Monoisotopic): 420.0845

AlogP: 4.09

#Rotatable Bonds: 4

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: 3.66

CX LogD: -3.30

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.37

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