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
UNII
6N4FA2QQ6A
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.