2,2-dimethyl-2H,3H,4H,5H,6H-naphtho[1,2-b]pyran-5,6-dione

• ChemBase ID: 106038
• Molecular Formular: C15H14O3
• Molecular Mass: 242.26986
• Monoisotopic Mass: 242.09429431
• SMILES: CC1(C)CCC2=C(O1)c1c(cccc1)C(=O)C2=O
• Canonical SMILES: O=C1C2=C(OC(CC2)(C)C)c2c(C1=O)cccc2
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,2-dimethyl-2H,3H,4H,5H,6H-naphtho[1,2-b]pyran-5,6-dione
• IUPAC Traditional name: β-lapachone
• Synonyms: β-Lapachone; ARQ-501; Beta-Lapachone; 3,4-Dihydro-2,2-dimethyl-2H-naphtho[1,2-b]pyran-5,6-dione; ARQ 501; NSC 26326; NSC 629749; SL 11001; β-Lapachone; β-LAPACHONE; β-Lapachone

Database IDs

• CAS Number: 4707-32-8
• MDL Number: MFCD01712233
• PubChem SID: 162087653; 24278512
• PubChem CID: 3885

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 2.6293175
• LogD (pH = 7.4): 2.6293175
• Log P: 2.6293175
• Molar Refractivity: 69.092 cm^3
• Polarizability: 26.07847 Å^3
• Polar Surface Area: 43.37 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Orange Solid
• Melting Point: >110°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer; Room Temperature (15-30°C)
• RTECS: QL6127400
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Target: Topoisomerase

Product Information

• Purity: ≥98%; ≥98% (TLC)
• Salt Data: Free Base

DETAILS

MP Biomedicals - 02196031

Purity: >98%
Novel DNA topoisomerase I inhibitor.

Sigma Aldrich - L2037

Biochem/physiol Actions
β-Lapachone is a naturally occurring quinone obtained from the bark of the lapacho tree (Tabebuia avellanedae) with cancer chemopreventive properties. Induces apoptosis in HL-60 and human prostate cancer cells.1

Toronto Research Chemicals - L175300

β-Lapachone is a naturally occurring quinone obtained from the bark of the lapacho tree (Tabebuia avellanedae) with cancer chemopreventive properties. Induces apoptosis in HL-60 and human prostate cancer cells.

REFERENCES

• Renslo, A., et al.: Nat. Chem. Biol., 2, 701 (2006)
• Hopkins, A., et al.: Nat. Chem. Biol., 4, 682 (2006)
• Stuart, K., et al.: J. Clin. Invest., 118, 1301 (2006)
• Martin, R., et al.: Science, 25, 1680 (2006)