Details of the Drug

General Information of Drug (ID: DMMI84K)

Drug 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
Indication
Disease Entry ICD 11 Status REF
Solid tumour/cancer 2A00-2F9Z Phase 2 [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 242.27
Logarithm of the Partition Coefficient (xlogp) 2.2
Rotatable Bond Count (rotbonds) 0
Hydrogen Bond Donor Count (hbonddonor) 0
Hydrogen Bond Acceptor Count (hbondacc) 3
Chemical Identifiers
Formula
C15H14O3
IUPAC Name
2,2-dimethyl-3,4-dihydrobenzo[h]chromene-5,6-dione
Canonical 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
Cross-matching ID
PubChem CID
3885
ChEBI ID
CHEBI:10429
CAS Number
4707-32-8
DrugBank ID
DB11948
TTD ID
D0W0VD
INTEDE ID
DR1869

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
DNA topoisomerase I (TOP1) TTGTQHC TOP1_HUMAN Modulator [1]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Quinone reductase 1 (NQO1)
Main DME 		DENP5RY NQO1_HUMAN Substrate [2]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Beclin-1 (BECN1) OT4X293M BECN1_HUMAN Drug Response [3]
NAD(P)H dehydrogenase 1 (NQO1) OTZGGIVK NQO1_HUMAN Biotransformations [4]
Ubiquitin-like modifier-activating enzyme ATG7 (ATG7) OTVT4YA1 ATG7_HUMAN Drug Response [3]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Solid tumour/cancer
ICD Disease Classification 2A00-2F9Z
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
DNA topoisomerase I (TOP1) DTT TOP1 6.65E-01 0.2 0.39
Quinone reductase 1 (NQO1) DME NQO1 6.02E-66 1.67E+00 2.21E+00
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 Cancer therapy with beta-lapachone. Curr Cancer Drug Targets. 2002 Sep;2(3):227-42.
2 Beta-lapachone, a modulator of NAD metabolism, prevents health declines in aged mice. PLoS One. 2012;7(10):e47122.
3 -Lapachone-induced reactive oxygen species (ROS) generation mediates autophagic cell death in glioma U87 MG cells. Chem Biol Interact. 2011 Jan 15;189(1-2):37-44. doi: 10.1016/j.cbi.2010.10.013. Epub 2010 Oct 28.
4 Human NAD(P)H:quinone oxidoreductase 1 (NQO1)-mediated inactivation of reactive quinoneimine metabolites of diclofenac and mefenamic acid. Chem Res Toxicol. 2014 Apr 21;27(4):576-86. doi: 10.1021/tx400431k. Epub 2014 Feb 26.