(R)-2,6-Diacetyl-3,7,9-trihydroxy-8,9b-dimethyl-9bH-dibenzofuran-1-one

ID: ALA367881

Chembl Id: CHEMBL367881

Max Phase: Preclinical

Molecular Formula: C18H16O7

Molecular Weight: 344.32

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Synonyms: (+)-Usnic acid | NSC-685596

Canonical SMILES:  CC(=O)C1=C(O)C=C2Oc3c(C(C)=O)c(O)c(C)c(O)c3[C@@]2(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/t18-/m0/s1

Standard InChI Key:  WEYVVCKOOFYHRW-SFHVURJKSA-N

Alternative Forms

  1. Parent:

Associated Targets(Human)

PTPN1 Tchem Protein-tyrosine phosphatase 1B (8528 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DU-145 (51482 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MCF7 (126967 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
K562 (73714 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
U-251 (51189 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HaCaT (4069 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
FBP1 Tchem Fructose-1,6-bisphosphatase (1199 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ELANE Tclin Leukocyte elastase (8173 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
A-431 (6446 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SLCO1B1 Tchem Solute carrier organic anion transporter family member 1B1 (2672 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SLCO1B3 Tchem Solute carrier organic anion transporter family member 1B3 (2517 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HL-60 (67320 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HeLa (62764 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

pol Human immunodeficiency virus type 1 integrase (9041 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Plasmodium falciparum (966862 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
L6 (7924 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
L1210 (27553 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CHO (4503 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
FBP1 Fructose-1,6-bisphosphatase (51 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ache Acetylcholinesterase (12221 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
BCHE Cholinesterase (8742 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
RAW264.7 (28094 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Influenza A virus (11224 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MDCK (10148 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Spodoptera littoralis (798 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Danio rerio (3092 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Escherichia coli (133304 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Mycobacterium tuberculosis (203094 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
fabI Enoyl-[acyl-carrier-protein] reductase (206 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Plasmodium berghei (192651 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Mus musculus (284745 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Rattus norvegicus (775804 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Vero (26788 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HPD 4-hydroxyphenylpyruvate dioxygenase (49 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: YesOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 344.32Molecular Weight (Monoisotopic): 344.0896AlogP: 2.13#Rotatable Bonds: 2
Polar Surface Area: 121.13Molecular Species: ACIDHBA: 7HBD: 3
#RO5 Violations: HBA (Lipinski): 7HBD (Lipinski): 3#RO5 Violations (Lipinski):
CX Acidic pKa: 3.62CX Basic pKa: CX LogP: 1.88CX LogD: -1.90
Aromatic Rings: 1Heavy Atoms: 25QED Weighted: 0.55Np Likeness Score: 1.98

References

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3. Bazin MA, Le Lamer AC, Delcros JG, Rouaud I, Uriac P, Boustie J, Corbel JC, Tomasi S..  (2008)  Synthesis and cytotoxic activities of usnic acid derivatives.,  16  (14): [PMID:18558490] [10.1016/j.bmc.2008.05.069]
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5. Kumar KC, Müller K..  (1999)  Lichen metabolites. 2. Antiproliferative and cytotoxic activity of gyrophoric, usnic, and diffractaic acid on human keratinocyte growth.,  62  (6): [PMID:10395495] [10.1021/np980378z]
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9. Sokolov DN, Zarubaev VV, Shtro AA, Polovinka MP, Luzina OA, Komarova NI, Salakhutdinov NF, Kiselev OI..  (2012)  Anti-viral activity of (-)- and (+)-usnic acids and their derivatives against influenza virus A(H1N1)2009.,  22  (23): [PMID:23099095] [10.1016/j.bmcl.2012.09.084]
10. Sokolov DN, Zarubaev VV, Shtro AA, Polovinka MP, Luzina OA, Komarova NI, Salakhutdinov NF, Kiselev OI..  (2012)  Anti-viral activity of (-)- and (+)-usnic acids and their derivatives against influenza virus A(H1N1)2009.,  22  (23): [PMID:23099095] [10.1016/j.bmcl.2012.09.084]
11. Giez I, Lange OL, Proksch P.  (1994)  Growth retarding activity of lichen substances against the polyphagous herbivorous insect Spodoptera littoralis,  22  (2): [10.1016/0305-1978(94)90001-9]
12. Lauinger IL, Vivas L, Perozzo R, Stairiker C, Tarun A, Zloh M, Zhang X, Xu H, Tonge PJ, Franzblau SG, Pham DH, Esguerra CV, Crawford AD, Maes L, Tasdemir D..  (2013)  Potential of lichen secondary metabolites against Plasmodium liver stage parasites with FAS-II as the potential target.,  76  (6): [PMID:23806111] [10.1021/np400083k]
13. Bruno M, Trucchi B, Burlando B, Ranzato E, Martinotti S, Akkol EK, Süntar I, Keleş H, Verotta L..  (2013)  (+)-Usnic acid enamines with remarkable cicatrizing properties.,  21  (7): [PMID:23434134] [10.1016/j.bmc.2013.01.045]
14. 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]
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16. Shtro AA, Zarubaev VV, Luzina OA, Sokolov DN, Kiselev OI, Salakhutdinov NF..  (2014)  Novel derivatives of usnic acid effectively inhibiting reproduction of influenza A virus.,  22  (24): [PMID:25464881] [10.1016/j.bmc.2014.10.033]
17. Yu X, Guo Q, Su G, Yang A, Hu Z, Qu C, Wan Z, Li R, Tu P, Chai X..  (2016)  Usnic Acid Derivatives with Cytotoxic and Antifungal Activities from the Lichen Usnea longissima.,  79  (5): [PMID:27186821] [10.1021/acs.jnatprod.6b00109]
18. Zakharenko A, Luzina O, Koval O, Nilov D, Gushchina I, Dyrkheeva N, Švedas V, Salakhutdinov N, Lavrik O..  (2016)  Tyrosyl-DNA Phosphodiesterase 1 Inhibitors: Usnic Acid Enamines Enhance the Cytotoxic Effect of Camptothecin.,  79  (11): [PMID:27933897] [10.1021/acs.jnatprod.6b00979]
19. Santucci A, Bernardini G, Braconi D, Petricci E, Manetti F..  (2017)  4-Hydroxyphenylpyruvate Dioxygenase and Its Inhibition in Plants and Animals: Small Molecules as Herbicides and Agents for the Treatment of Human Inherited Diseases.,  60  (10): [PMID:28128559] [10.1021/acs.jmedchem.6b01395]
20. Zakharenko AL, Luzina OA, Sokolov DN, Kaledin VI, Nikolin VP, Popova NA, Patel J, Zakharova OD, Chepanova AA, Zafar A, Reynisson J, Leung E, Leung IKH, Volcho KP, Salakhutdinov NF, Lavrik OI..  (2019)  Novel tyrosyl-DNA phosphodiesterase 1 inhibitors enhance the therapeutic impact of topoteсan on in vivo tumor models.,  161  [PMID:30396105] [10.1016/j.ejmech.2018.10.055]
21. Gunawan GA, Gimła M, Gardiner MG, Herman-Antosiewicz A, Reekie TA..  (2023)  Divergent reactivity of usnic acid and evaluation of its derivatives for antiproliferative activity against cancer cells.,  79  [PMID:36652792] [10.1016/j.bmc.2023.117157]

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