(-)-usnic acid

ID: ALA461903

Chembl Id: CHEMBL461903

Max Phase: Preclinical

Molecular Formula: C18H16O7

Molecular Weight: 344.32

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Synonyms: (+)-Usnic Acid | (-)-Usnic Acid

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-/m1/s1

Standard InChI Key:  WEYVVCKOOFYHRW-GOSISDBHSA-N

Alternative Forms

  1. Parent:

Associated Targets(Human)

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
MEN1 Tchem Menin/Histone-lysine N-methyltransferase MLL (48157 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
BRCA1 Tchem Breast cancer type 1 susceptibility protein (15908 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ALDH1A1 Tchem Aldehyde dehydrogenase 1A1 (77053 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ALOX15 Tchem Arachidonate 15-lipoxygenase (7108 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP2C9 Tchem Cytochrome P450 2C9 (32119 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
BT-474 (2113 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SK-BR-3 (5175 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
T47D (39041 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MDA-MB-468 (9477 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MDA-MB-231 (73002 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MTOR Tclin Serine/threonine-protein kinase mTOR (13850 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MTOR Tclin mTORC2 (162 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Staphylococcus aureus (210822 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Escherichia coli (133304 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Salmonella enterica subsp. enterica serovar Gallinarum (105 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Klebsiella pneumoniae (43867 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Mycolicibacterium smegmatis (8003 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Candida albicans (78123 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Pseudomonas aeruginosa (123386 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
lef Anthrax lethal factor (7585 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
P388 (20296 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: 0HBA (Lipinski): 7HBD (Lipinski): 3#RO5 Violations (Lipinski): 0
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

1. Gollapudi SR, Telikepalli H, Jampani HB, Mirhom YW, Drake SD, Bhattiprolu KR, Vander Velde D, Mitscher LA..  (1994)  Alectosarmentin, a new antimicrobial dibenzofuranoid lactol from the lichen, Alectoria sarmentosa.,  57  (7): [PMID:7964789] [10.1021/np50109a009]
2. 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]
3. PubChem BioAssay data set, 
4. PubChem BioAssay data set, 
5. 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]
6. 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]
7. Takai M, Uehara Y, Beisler JA..  (1979)  Usnic acid derivatives as potential antineoplastic agents.,  22  (11): [PMID:160461] [10.1021/jm00197a019]
8. 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]
9. 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]
10. Ebrahim HY, Akl MR, Elsayed HE, Hill RA, El Sayed KA..  (2017)  Usnic Acid Benzylidene Analogues as Potent Mechanistic Target of Rapamycin Inhibitors for the Control of Breast Malignancies.,  80  (4): [PMID:28245124] [10.1021/acs.jnatprod.6b00917]