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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2022-03-07 02:52:03 UTC
HMDB IDHMDB0015607
Secondary Accession Numbers
  • HMDB15607
Metabolite Identification
Common NameLucanthone
DescriptionLucanthone is only found in individuals that have used or taken this drug. It is one of the schistosomicides, it has been replaced largely by hycanthone and more recently praziquantel. (From Martindale The Extrapharmacopoeia, 30th ed., p46). It is currently being tested as a radiation sensitizer.Recent data suggests that lucanthone inhibits post-radiation DNA repair in tumor cells. The ability of lucanthone to inhibit AP endonuclease and topoisomerase II probably account for the specific DNA repair inhibition in irradiated cells.
Structure
Data?1582753316
Synonyms
ValueSource
1-((2-(Diethylamino)ethyl)amino)-4-methylthioxanthen-9-oneChEBI
1-Diethylaminoethylethylamino-4-methyl-thioxanthenoneChEBI
1-{[2-(diethylamino)ethyl]amino}-4-methylthioxanthen-9-oneChEBI
LucanthonumChEBI
LucantonaChEBI
1-[[2-(Diethylamino)ethyl]amino]-4-methylthioxanthoneHMDB
LucanthonHMDB
Lucanthone monohydrochlorideHMDB
Lucanthone hydrochlorideHMDB
TixantoneHMDB
Miracil DHMDB
Chemical FormulaC20H24N2OS
Average Molecular Weight340.482
Monoisotopic Molecular Weight340.16093409
IUPAC Name1-{[2-(diethylamino)ethyl]amino}-4-methyl-9H-thioxanthen-9-one
Traditional Namelucanthone
CAS Registry Number479-50-5
SMILES
CCN(CC)CCNC1=C2C(=O)C3=CC=CC=C3SC2=C(C)C=C1
InChI Identifier
InChI=1S/C20H24N2OS/c1-4-22(5-2)13-12-21-16-11-10-14(3)20-18(16)19(23)15-8-6-7-9-17(15)24-20/h6-11,21H,4-5,12-13H2,1-3H3
InChI KeyFBQPGGIHOFZRGH-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as thiochromenes. These are organosulfur compounds that are analogues to chromene, with the difference that are sulfur atom replaces the oxygen atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassThiochromenes
Sub ClassNot Available
Direct ParentThiochromenes
Alternative Parents
Substituents
  • Thiochromene
  • Benzothiopyran
  • 1-benzothiopyran
  • Secondary aliphatic/aromatic amine
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous amide
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0032 g/LNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0032 g/LALOGPS
logP4.72ALOGPS
logP5.02ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)18.84ChemAxon
pKa (Strongest Basic)8.69ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area32.34 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity106.01 m³·mol⁻¹ChemAxon
Polarizability39.6 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+180.38831661259
DarkChem[M-H]-177.78531661259
DeepCCS[M+H]+184.84230932474
DeepCCS[M-H]-182.48430932474
DeepCCS[M-2H]-215.58430932474
DeepCCS[M+Na]+190.93630932474
AllCCS[M+H]+180.532859911
AllCCS[M+H-H2O]+177.432859911
AllCCS[M+NH4]+183.332859911
AllCCS[M+Na]+184.132859911
AllCCS[M-H]-186.032859911
AllCCS[M+Na-2H]-185.732859911
AllCCS[M+HCOO]-185.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
LucanthoneCCN(CC)CCNC1=C2C(=O)C3=CC=CC=C3SC2=C(C)C=C14156.5Standard polar33892256
LucanthoneCCN(CC)CCNC1=C2C(=O)C3=CC=CC=C3SC2=C(C)C=C13098.7Standard non polar33892256
LucanthoneCCN(CC)CCNC1=C2C(=O)C3=CC=CC=C3SC2=C(C)C=C13239.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Lucanthone,1TMS,isomer #1CCN(CC)CCN(C1=CC=C(C)C2=C1C(=O)C1=CC=CC=C1S2)[Si](C)(C)C2946.7Semi standard non polar33892256
Lucanthone,1TMS,isomer #1CCN(CC)CCN(C1=CC=C(C)C2=C1C(=O)C1=CC=CC=C1S2)[Si](C)(C)C2958.3Standard non polar33892256
Lucanthone,1TMS,isomer #1CCN(CC)CCN(C1=CC=C(C)C2=C1C(=O)C1=CC=CC=C1S2)[Si](C)(C)C3453.9Standard polar33892256
Lucanthone,1TBDMS,isomer #1CCN(CC)CCN(C1=CC=C(C)C2=C1C(=O)C1=CC=CC=C1S2)[Si](C)(C)C(C)(C)C3141.9Semi standard non polar33892256
Lucanthone,1TBDMS,isomer #1CCN(CC)CCN(C1=CC=C(C)C2=C1C(=O)C1=CC=CC=C1S2)[Si](C)(C)C(C)(C)C3117.0Standard non polar33892256
Lucanthone,1TBDMS,isomer #1CCN(CC)CCN(C1=CC=C(C)C2=C1C(=O)C1=CC=CC=C1S2)[Si](C)(C)C(C)(C)C3543.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Lucanthone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0zi9-9052000000-539114a80db1e32eb9a22017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lucanthone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lucanthone 10V, Positive-QTOFsplash10-0006-1219000000-50d0c1ff5c50d70b44312016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lucanthone 20V, Positive-QTOFsplash10-0uxr-4892000000-0bb96e502a524f51b2032016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lucanthone 40V, Positive-QTOFsplash10-0fmi-9240000000-ca20c5fb0c954a7a972b2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lucanthone 10V, Negative-QTOFsplash10-000i-0019000000-ba002b772294de47ce3f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lucanthone 20V, Negative-QTOFsplash10-000i-3049000000-a845a36b91098f229d502016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lucanthone 40V, Negative-QTOFsplash10-006x-9250000000-a6c9d2e8f2de1502d55c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lucanthone 10V, Positive-QTOFsplash10-0006-0009000000-0e4a03265785e2302ee02021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lucanthone 20V, Positive-QTOFsplash10-0006-0219000000-c11e2a98f430732b92052021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lucanthone 40V, Positive-QTOFsplash10-0fk9-9450000000-47cea156c4178a4990ee2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lucanthone 10V, Negative-QTOFsplash10-000i-0009000000-301993047e54373ba45d2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lucanthone 20V, Negative-QTOFsplash10-000i-0069000000-dab0fdc698464727ec212021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lucanthone 40V, Negative-QTOFsplash10-0fb9-0190000000-f557d9b5c78b2d05b5432021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB04967 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB04967 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB04967
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID9772
KEGG Compound IDC11715
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLucanthone
METLIN IDNot Available
PubChem Compound10180
PDB IDNot Available
ChEBI ID51052
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Luo M, Kelley MR: Inhibition of the human apurinic/apyrimidinic endonuclease (APE1) repair activity and sensitization of breast cancer cells to DNA alkylating agents with lucanthone. Anticancer Res. 2004 Jul-Aug;24(4):2127-34. [PubMed:15330152 ]
  2. Del Rowe JD, Bello J, Mitnick R, Sood B, Filippi C, Moran J, Freeman K, Mendez F, Bases R: Accelerated regression of brain metastases in patients receiving whole brain radiation and the topoisomerase II inhibitor, lucanthone. Int J Radiat Oncol Biol Phys. 1999 Jan 1;43(1):89-93. [PubMed:9989518 ]

Enzymes

General function:
Involved in DNA binding
Specific function:
Repairs oxidative DNA damages in vitro. May have a role in protection against cell lethality and suppression of mutations. Removes the blocking groups from the 3'-termini of the DNA strand breaks generated by ionizing radiations and bleomycin
Gene Name:
APEX1
Uniprot ID:
P27695
Molecular weight:
35554.2
References
  1. Luo M, Kelley MR: Inhibition of the human apurinic/apyrimidinic endonuclease (APE1) repair activity and sensitization of breast cancer cells to DNA alkylating agents with lucanthone. Anticancer Res. 2004 Jul-Aug;24(4):2127-34. [PubMed:15330152 ]
General function:
Involved in sequence-specific DNA binding transcription factor activity
Specific function:
Control of topological states of DNA by transient breakage and subsequent rejoining of DNA strands. Topoisomerase II makes double-strand breaks
Gene Name:
TOP2A
Uniprot ID:
P11388
Molecular weight:
174383.9
References
  1. Bases RE, Mendez F: Topoisomerase inhibition by lucanthone, an adjuvant in radiation therapy. Int J Radiat Oncol Biol Phys. 1997 Mar 15;37(5):1133-7. [PubMed:9169823 ]
  2. Dassonneville L, Bailly C: Stimulation of topoisomerase II-mediated DNA cleavage by an indazole analogue of lucanthone. Biochem Pharmacol. 1999 Oct 15;58(8):1307-12. [PubMed:10487533 ]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]