Rubitecan (CHEM019227)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 05:56:02 UTC
Update Date2016-11-09 01:15:57 UTC
Accession NumberCHEM019227
Identification
Common NameRubitecan
ClassSmall Molecule
DescriptionA pyranoindolizinoquinoline that is camptothecin in which the hydrogen at position 9 has been replaced by a nitro group. It is a prodrug for 9-aminocamptothecin.
Contaminant Sources
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
9-NCChEBI
9-Nitro-(20S)-camptothecinChEBI
9-Nitro-20(S)-camptothecinChEBI
9-NitrocamptothecinChEBI
CamptogenChEBI
OrathecinChEBI
RFS 2000ChEBI
RubitecanumChEBI
9-Nitrocamptothecin, (S)-isomerMeSH
Chemical FormulaC20H15N3O6
Average Molecular Mass393.355 g/mol
Monoisotopic Mass393.096 g/mol
CAS Registry Number91421-42-0
IUPAC Name(19S)-19-ethyl-19-hydroxy-8-nitro-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-1(21),2,4(9),5,7,10,15(20)-heptaene-14,18-dione
Traditional Name(19S)-19-ethyl-19-hydroxy-8-nitro-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-1(21),2,4(9),5,7,10,15(20)-heptaene-14,18-dione
SMILESCC[C@@]1(O)C(=O)OCC2=C1C=C1N(CC3=CC4=C(C=CC=C4N(=O)=O)N=C13)C2=O
InChI IdentifierInChI=1S/C20H15N3O6/c1-2-20(26)13-7-16-17-10(8-22(16)18(24)12(13)9-29-19(20)25)6-11-14(21-17)4-3-5-15(11)23(27)28/h3-7,26H,2,8-9H2,1H3/t20-/m0/s1
InChI KeyVHXNKPBCCMUMSW-FQEVSTJZSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1-naphthalene sulfonic acids and derivatives. These are organic aromatic compounds that contain a naphthalene moiety that carries a sulfonic acid group (or a derivative thereof) at the 1-position. Naphthalene is a bicyclic compound that is made up of two fused benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassNaphthalenes
Sub ClassNaphthalene sulfonic acids and derivatives
Direct Parent1-naphthalene sulfonic acids and derivatives
Alternative Parents
Substituents
  • 1-naphthalene sulfonamide
  • Naphthalene sulfonamide
  • 1-naphthalene sulfonic acid or derivatives
  • Phenylpiperazine
  • N-arylpiperazine
  • 1,2-benzothiazole
  • Tertiary aliphatic/aromatic amine
  • Aniline or substituted anilines
  • Dialkylarylamine
  • Fluorobenzene
  • Halobenzene
  • N-alkylpiperazine
  • Aryl fluoride
  • Organosulfonic acid amide
  • Piperazine
  • Aryl halide
  • Monocyclic benzene moiety
  • 1,4-diazinane
  • Organosulfonic acid or derivatives
  • Organic sulfonic acid or derivatives
  • Tertiary aliphatic amine
  • Tertiary amine
  • Organoheterocyclic compound
  • Azacycle
  • Organic oxide
  • Organohalogen compound
  • Amine
  • Organofluoride
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • 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
Water Solubility0.24 g/LALOGPS
logP1.88ALOGPS
logP1.16ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)11.63ChemAxon
pKa (Strongest Basic)0.52ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area125.55 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity101.82 m³·mol⁻¹ChemAxon
Polarizability39.03 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0009000000-01ace8e8efc379416f82Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002b-0009000000-7b757e06c29f3691276fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-6598000000-98a3e4469d3088ec4163Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0009000000-517fa2a71b5ecc0d6c32Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0009000000-7e1fafa9bb888cc04b79Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-8049000000-5d999f188752eb49b0cdSpectrum
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 IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkRubitecan
Chemspider IDNot Available
ChEBI ID90225
PubChem Compound ID472335
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10200331
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=11901310
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=15122081
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=15357630
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=16370935
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=21191594
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=21695227
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=23873658
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=23934323
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=24549232
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=25445521
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=26004006
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=26487893