Natural Product (NP) Details

General Information of the NP (ID: NP6452)
Name
Beta lapachone
Synonyms
ARQ 501; SL 11001; A-lapachone; LAPACHONE, BETA; AK-693/21096016; 2,2-dimethyl-3,4-dihydrobenzo[h]chromene-5,6-dione; 3,4-Dihydro-2,2-dimethyl-2H-naphtho(1,2-b)pyran-5,6-dione; 3,4-Dihydro-2,2-dimethyl-2H-naphtho[1,2-B]pyran-5,6-dione
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Species Origin Tabebuia avellanedae ...     Click to Show/Hide
Tabebuia avellanedae
SuperKingdom: Eukaryota
Phylum: Mollusca
Class: Gastropoda
Order: Stylommatophora
Family: Orthalicidae
Genus: Cyclodontina
Species: Tabebuia avellanedae
Disease Solid tumour/cancer [ICD-11: 2A00-2F9Z] Phase 2 [1]
Structure
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2D MOL

3D MOL

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Formula
C15H14O3
PubChem CID
3885
Canonical SMILES
CC1(CCC2=C(O1)C3=CC=CC=C3C(=O)C2=O)C
InChI
1S/C15H14O3/c1-15(2)8-7-11-13(17)12(16)9-5-3-4-6-10(9)14(11)18-15/h3-6H,7-8H2,1-2H3
InChIKey
QZPQTZZNNJUOLS-UHFFFAOYSA-N
CAS Number
CAS 4707-32-8
TTD Drug ID
D0W0VD
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          Fluconazole      Fungal infection     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model Candida albicans Microorganism model Candida albicans
                    Experimental
                    Result(s)		 Beta-lapachone reverted antifungal resistance of S. cerevisiae and C. albicans strains overexpressing CaCdr2p and CaMdr1p transporters by inhibiting these proteins activities. CaCdr2p ATPase activity was not impaired by the compound.
          Ionizing radiation      Renal Insufficiency     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model DU145 CVCL_0105 Prostate carcinoma Homo sapiens
                    Experimental
                    Result(s)		 The synergistic interaction between beta-lap and radiation in killing cells is the result of two distinct mechanisms: First, radiation sensitizes cells to beta-lap by up-regulating NQO1, and second, beta-lap sensitizes cells to radiation by inhibiting SLD repair.
Target and Pathway
Target(s) DNA topoisomerase I (TOP1)  Molecule Info  [1]
NetPath Pathway IL2 Signaling Pathway Click to Show/Hide
Panther Pathway DNA replication Click to Show/Hide
Pathway Interaction Database Caspase Cascade in Apoptosis Click to Show/Hide
WikiPathways Integrated Pancreatic Cancer Pathway Click to Show/Hide
References
Reference 1 Cancer therapy with beta-lapachone. Curr Cancer Drug Targets. 2002 Sep;2(3):227-42.
Reference 2 Synergistic interactions between Beta-lapachone and fluconazole in the inhibition of CaCdr2p and CaMdr1p in Candida albicans. Rev Iberoam Micol. Jul-Oct 2020;37(3-4):104-106.
Reference 3 Synergistic effects of radiation and beta-lapachone in DU-145 human prostate cancer cells in vitro. Radiat Res. 2006 May;165(5):525-31.
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