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β-Lapachone (Standard)

CAT: 0804-HY-13555R-04Size: 50 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-13555R-04Size:50 mg
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Description
β-Lapachone (Standard) is the analytical standard of β-Lapachone. This product is intended for research and analytical applications. β-Lapachone (ARQ-501; NSC-26326) is a naturally occurring O-naphthoquinone, acts as a topoisomerase I inhibitor, and induces apoptosis by inhibiting cell cycle progression.
CAS Number
4707-32-8
UNSPSC
12352100
Target
Apoptosis; Autophagy; Indoleamine 2,3-Dioxygenase (IDO) ; Reference Standards; Topoisomerase
Related Pathways
Apoptosis; Autophagy; Cell Cycle/DNA Damage; Metabolic Enzyme/Protease; Others
Field of Research
Cancer
Smiles
O=C(C1=C2OC(C)(C)CC1)C(C3=C2C=CC=C3)=O
Molecular Formula
C15H14O3
Molecular Weight
242.27
References & Citations
[1]Li CJ, et al. beta-Lapachone, a novel DNA topoisomerase I inhibitor with a mode of action different from camptothecin. J Biol Chem. 1993 Oct 25;268 (30) :22463-8.|[2]Vanni A, et al. DNA damage and cytotoxicity induced by beta-lapachone: relation to poly (ADP-ribose) polymerase inhibition. Mutat Res. 1998 Jun 5;401 (1-2) :55-63.|[3]Kim TW, et al. β-Lapachone enhances Mre11-Rad50-Nbs1 complex expression in cisplatin-induced nephrotoxicity. Pharmacol Rep. 2016 Feb;68 (1) :27-31.
Shipping Conditions
Room temperature
Scientific Category
Reference Standards

Chemical Information

Beta-Lapachone

Beta-lapachone is a benzochromenone that is 3,4-dihydro-2H-benzo[h]chromene-5,6-dione substituted by geminal methyl groups at position 2. Isolated from Tabebuia avellanedae, it exhibits antineoplastic and anti-inflammatory activities. It has a role as an antineoplastic agent, an anti-inflammatory agent and a plant metabolite. It is a member of orthoquinones and a benzochromenone.

CAS Number4707-32-8
PubChem CID3885
IUPAC Name2,2-dimethyl-3,4-dihydrobenzo[h]chromene-5,6-dione
Molecular FormulaC15H14O3
Molecular Weight242.27
XLogP2.2
Topological Polar Surface Area43.4
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count3
Rotatable Bond Count0
Heavy Atom Count18
Formal Charge0
Complexity445
SMILES
CC1(CCC2=C(O1)C3=CC=CC=C3C(=O)C2=O)C
InChI
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
Chemical Structure
2D Structure
2D structure of Beta-Lapachone
CAS: 4707-32-8
CID: 3885
Formula: C15H14O3
MW: 242.27
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight242.27
XLogP32.2
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count3
Rotatable Bond Count0
Exact Mass242.094294304
Monoisotopic Mass242.094294304
Topological Polar Surface Area43.4 Ų
Heavy Atom Count18
Formal Charge0
Complexity445
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

Related Products

CatalogName
HY-N2848-01α-Lapachone
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T60291-01β-Nor-lapachone

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