Topotecan hydrochloride (CHEM018662)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 05:25:36 UTC
Update Date2016-11-09 01:15:51 UTC
Accession NumberCHEM018662
Identification
Common NameTopotecan hydrochloride
ClassSmall Molecule
DescriptionNot Available
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Nogitecan hydrochlorideKegg
HycamtinKegg
PotactasolKegg
9 Dimethylaminomethyl 10 hydroxycamptothecinMeSH
9-Dimethylaminomethyl-10-hydroxycamptothecinMeSH
HycamtamineMeSH
Hydrochloride, nogitecanMeSH
Hydrochloride, topotecanMeSH
SK And F 104864 aMeSH
SK And F-104864-aMeSH
SK And F104864aMeSH
TopotecanMeSH
Topotecan monohydrochloride, (S)-isomerMeSH
Topotecan hydrochlorideKEGG
Chemical FormulaC23H24ClN3O5
Average Molecular Mass457.907 g/mol
Monoisotopic Mass457.140 g/mol
CAS Registry Number119413-54-6
IUPAC Name(19S)-8-[(dimethylamino)methyl]-19-ethyl-7,19-dihydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-1(21),2(11),3,5,7,9,15(20)-heptaene-14,18-dione hydrochloride
Traditional Nametopotecan hydrochloride
SMILESCl.CC[C@@]1(O)C(=O)OCC2=C1C=C1N(CC3=C1N=C1C=CC(O)=C(CN(C)C)C1=C3)C2=O
InChI IdentifierInChI=1S/C23H23N3O5.ClH/c1-4-23(30)16-8-18-20-12(9-26(18)21(28)15(16)11-31-22(23)29)7-13-14(10-25(2)3)19(27)6-5-17(13)24-20;/h5-8,27,30H,4,9-11H2,1-3H3;1H/t23-;/m0./s1
InChI KeyDGHHQBMTXTWTJV-BQAIUKQQSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as camptothecins. These are heterocyclic compounds comprising a planar pentacyclic ring structure, that includes a pyrrolo[3,4-beta]-quinoline moiety (rings A, B and C), conjugated pyridone moiety (ring D) and one chiral center at position 20 within the alpha-hydroxy lactone ring with (S) configuration (the E-ring).
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassCamptothecins
Sub ClassNot Available
Direct ParentCamptothecins
Alternative Parents
Substituents
  • Camptothecin
  • Hydroxyquinoline
  • Pyranopyridine
  • Quinoline
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyridinone
  • Aralkylamine
  • Pyridine
  • Benzenoid
  • Heteroaromatic compound
  • Tertiary alcohol
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Lactam
  • Lactone
  • Tertiary amine
  • Tertiary aliphatic amine
  • Oxacycle
  • Organoheterocyclic compound
  • Azacycle
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Amine
  • Alcohol
  • Organic nitrogen compound
  • Carbonyl group
  • Hydrochloride
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
logP-0.36ChemAxon
pKa (Strongest Acidic)8ChemAxon
pKa (Strongest Basic)9.83ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area103.2 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity115.02 m³·mol⁻¹ChemAxon
Polarizability44.85 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00b9-0019400000-9445fd14e8560bc2d06fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000900000-53f8666f73557ba8efb5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0000900000-53f8666f73557ba8efb5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-0000900000-53f8666f73557ba8efb5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000900000-29b79f324e703bfa4feaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0000900000-29b79f324e703bfa4feaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0000900000-29b79f324e703bfa4feaSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDBSALT000322
HMDB IDHMDB0301823
FooDB IDFDB001461
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID54704
ChEBI IDNot Available
PubChem Compound ID60699
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available