Usnic acid

ID: ALA242022

Chembl Id: CHEMBL242022

Max Phase: Preclinical

Molecular Formula: C18H16O7

Molecular Weight: 344.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)C1=C(O)C=C2Oc3c(C(C)=O)c(O)c(C)c(O)c3C2(C)C1=O

Standard InChI:  InChI=1S/C18H16O7/c1-6-14(22)12(8(3)20)16-13(15(6)23)18(4)10(25-16)5-9(21)11(7(2)19)17(18)24/h5,21-23H,1-4H3

Standard InChI Key:  WEYVVCKOOFYHRW-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA242022

   ---

2. Alternative Forms:

   

   ALA242022

   2,6-Diacetyl-3,7,9-trihydroxy-8,9b-dimethyldibenzofuran-1-one;hydrochloride

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: 344.32

Molecular Weight (Monoisotopic): 344.0896

AlogP: 2.13

#Rotatable Bonds: 2

Polar Surface Area: 121.13

Molecular Species: ACID

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.62

CX Basic pKa: ┄

CX LogP: 1.88

CX LogD: -1.90

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.55

Np Likeness Score: 1.98

References

1. Surineni G, Yogeeswari P, Sriram D, Kantevari S..  (2016)  Click-based synthesis and antitubercular evaluation of dibenzofuran tethered thiazolyl-1,2,3-triazolyl acetamides.,  26  (15): [PMID:27317646] [10.1016/j.bmcl.2016.05.085]

2.  (2016)  Dibenzofuran derivatives as inhibitors of fructose 1,6-bisphosphatase and methods of use thereof, 

3. Victor K, Boris L, Athina G, Anthi P, Marija S, Marina K, Oliver R, Marina S..  (2018)  Design, synthesis and antimicrobial activity of usnic acid derivatives.,  9  (5): [PMID:30108976] [10.1039/C8MD00076J]

4. Bangalore PK, Vagolu SK, Bollikanda RK, Veeragoni DK, Choudante PC, Misra S, Sriram D, Sridhar B, Kantevari S..  (2020)  Usnic Acid Enaminone-Coupled 1,2,3-Triazoles as Antibacterial and Antitubercular Agents.,  83  (1): [PMID:31858800] [10.1021/acs.jnatprod.9b00475]

5. Aldrich LN, Burdette JE, Carcache de Blanco E, Coss CC, Eustaquio AS, Fuchs JR, Kinghorn AD, MacFarlane A, Mize BK, Oberlies NH, Orjala J, Pearce CJ, Phelps MA, Rakotondraibe LH, Ren Y, Soejarto DD, Stockwell BR, Yalowich JC, Zhang X..  (2022)  Discovery of Anticancer Agents of Diverse Natural Origin.,  85  (3.0): [PMID:35213158] [10.1021/acs.jnatprod.2c00036]

Source

Source(2):

• Scientific Literature
• BindingDB Database