6-Bromo-2,8-dioxo-2,8-dihydropyrano[2,3-f]chromene-3,9-dicarboxylic Acid

ID: ALA4848949

PubChem CID: 154634323

Max Phase: Preclinical

Molecular Formula: C14H5BrO8

Molecular Weight: 381.09

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C14H5BrO8/c15-8-2-4-1-6(11(16)17)13(20)22-9(4)5-3-7(12(18)19)14(21)23-10(5)8/h1-3H,(H,16,17)(H,18,19)

Standard InChI Key:  IFOGUCVJAXMZEF-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    4.4890  -10.7390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1941  -10.3301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1959  -11.9675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4909  -11.5583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7879  -11.9621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7838  -12.7766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4888  -13.1858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1980  -12.7804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9027  -10.7354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9016  -11.5561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6078  -11.9651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3197  -11.5581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3208  -10.7374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6101  -10.3238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0746  -13.1826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0262  -11.9686    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0296  -10.3296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7363  -10.7399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0315   -9.5124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4869  -14.0065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7779  -14.4128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1933  -14.4174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7804  -10.3319    0.0000 Br  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
  1 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4848949

   ---

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: 381.09

Molecular Weight (Monoisotopic): 379.9168

AlogP: 2.06

#Rotatable Bonds: 2

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: 1.62

CX Basic pKa: ┄

CX LogP: 1.54

CX LogD: -5.51

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.51

Np Likeness Score: 0.24

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