(6E,8E)-3,4,6-trihydroxy-5-oxo-5H-benzo[7]annulene-8-carboxylic acid

ID: ALA559337

Chembl Id: CHEMBL559337

PubChem CID: 5098885

Max Phase: Preclinical

Molecular Formula: C12H8O6

Molecular Weight: 248.19

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1cc(O)c(=O)c2c(O)c(O)ccc2c1

Standard InChI:  InChI=1S/C12H8O6/c13-7-2-1-5-3-6(12(17)18)4-8(14)11(16)9(5)10(7)15/h1-4,13,15H,(H,14,16)(H,17,18)

Standard InChI Key:  XCSLJQFPTAZKDV-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA559337

   7-DESHYDROXYPYROGALLIN-4-CARBOXYLIC ACID

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 248.19

Molecular Weight (Monoisotopic): 248.0321

AlogP: 1.01

#Rotatable Bonds: 1

Polar Surface Area: 115.06

Molecular Species: ACID

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.50

CX Basic pKa: 3.24

CX LogP: 1.01

CX LogD: -1.95

Aromatic Rings: 2

Heavy Atoms: 18

QED Weighted: 0.56

Np Likeness Score: 1.08

References

1. Kirschberg TA, Balakrishnan M, Squires NH, Barnes T, Brendza KM, Chen X, Eisenberg EJ, Jin W, Kutty N, Leavitt S, Liclican A, Liu Q, Liu X, Mak J, Perry JK, Wang M, Watkins WJ, Lansdon EB..  (2009)  RNase H active site inhibitors of human immunodeficiency virus type 1 reverse transcriptase: design, biochemical activity, and structural information.,  52  (19): [PMID:19791799] [10.1021/jm900597q]

2. Deng H, Hu H, Ling S, Ferrie AM, Fang Y..  (2012)  Discovery of Natural Phenols as G Protein-Coupled Receptor-35 (GPR35) Agonists.,  3  (2): [PMID:24900447] [10.1021/ml2003058]

3. De Bruyn T, van Westen GJ, Ijzerman AP, Stieger B, de Witte P, Augustijns PF, Annaert PP..  (2013)  Structure-based identification of OATP1B1/3 inhibitors.,  83  (6): [PMID:23571415] [10.1124/mol.112.084152]

4. Cleenewerck M, Grootaert MOJ, Gladysz R, Adriaenssens Y, Roelandt R, Joossens J, Lambeir AM, De Meyer GRY, Declercq W, Augustyns K, Martinet W, Van der Veken P..  (2016)  Inhibitor screening and enzymatic activity determination for autophagy target Atg4B using a gel electrophoresis-based assay.,  123  [PMID:27517808] [10.1016/j.ejmech.2016.07.073]

5.  (2014)  Antagonists of the toll-like receptor 1/2 complex, 

6. Kim B, Jo S, Park SB, Chae CH, Lee K, Koh B, Shin I..  (2020)  Development and structure-activity relationship study of SHP2 inhibitor containing 3,4,6-trihydroxy-5-oxo-5H-benzo[7]annulene.,  30  (1): [PMID:31784318] [10.1016/j.bmcl.2019.126756]

7. Stevens M, Abdeen S, Salim N, Ray AM, Washburn A, Chitre S, Sivinski J, Park Y, Hoang QQ, Chapman E, Johnson SM..  (2019)  HSP60/10 chaperonin systems are inhibited by a variety of approved drugs, natural products, and known bioactive molecules.,  29  (9): [PMID:30852084] [10.1016/j.bmcl.2019.02.028]

8. Song Y, Wang S, Zhao M, Yang X, Yu B..  (2022)  Strategies Targeting Protein Tyrosine Phosphatase SHP2 for Cancer Therapy.,  65  (4.0): [PMID:35157464] [10.1021/acs.jmedchem.1c02008]

9. Yang G, Li Y, Zhao Y, Ouyang L, Chen Y, Liu B, Liu J..  (2021)  Targeting Atg4B for cancer therapy: Chemical mediators.,  209  [PMID:33077263] [10.1016/j.ejmech.2020.112917]

Source

Source(2):

• Scientific Literature
• Patent Bioactivity Data