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Record Information
Version4.0
Creation Date2013-06-15 17:09:54 UTC
Update Date2017-09-27 08:43:50 UTC
HMDB IDHMDB0060586
Secondary Accession Numbers
  • HMDB60586
Metabolite Identification
Common NameN-Trifluoroacetyladriamycinol
DescriptionN-Trifluoroacetyladriamycinol is a metabolite of valrubicin. Valrubicin (N-trifluoroacetyladriamycin-14-valerate, trade name Valstar) is a chemotherapy drug used to treat bladder cancer. Valrubicin is a semisynthetic analog of the anthracycline doxorubicin, and is administered by infusion directly into the bladder. It was originally launched as Valstar in the U.S. (Wikipedia)
Structure
Thumb
Synonyms
ValueSource
AD 92MeSH
AD-P2MeSH
Chemical FormulaC29H30F3NO12
Average Molecular Weight641.5432
Monoisotopic Molecular Weight641.172010044
IUPAC NameN-(6-{[3-(1,2-dihydroxyethyl)-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl]oxy}-3-hydroxy-2-methyloxan-4-yl)-2,2,2-trifluoroethanimidic acid
Traditional NameN-(6-{[3-(1,2-dihydroxyethyl)-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-2,4-dihydro-1H-tetracen-1-yl]oxy}-3-hydroxy-2-methyloxan-4-yl)-2,2,2-trifluoroethanimidic acid
CAS Registry NumberNot Available
SMILES
COC1=CC=CC2=C1C(=O)C1=C(C(O)=C3CC(O)(CC(OC4CC(N=C(O)C(F)(F)F)C(O)C(C)O4)C3=C1O)C(O)CO)C2=O
InChI Identifier
InChI=1S/C29H30F3NO12/c1-10-22(36)13(33-27(41)29(30,31)32)6-17(44-10)45-15-8-28(42,16(35)9-34)7-12-19(15)26(40)21-20(24(12)38)23(37)11-4-3-5-14(43-2)18(11)25(21)39/h3-5,10,13,15-17,22,34-36,38,40,42H,6-9H2,1-2H3,(H,33,41)
InChI KeyTWMWXCYMYAQOTO-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as anthracyclines. These are polyketides containing a tetracenequinone ring structure with a sugar attached by glycosidic linkage.
KingdomChemical entities
Super ClassOrganic compounds
ClassPhenylpropanoids and polyketides
Sub ClassAnthracyclines
Direct ParentAnthracyclines
Alternative Parents
Substituents
  • Anthracycline
  • Anthracyclinone-skeleton
  • Tetracenequinone
  • 9,10-anthraquinone
  • 1,4-anthraquinone
  • Anthracene
  • Hexose monosaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Tetralin
  • Anisole
  • Aryl ketone
  • Alkyl aryl ether
  • Benzenoid
  • Monosaccharide
  • Oxane
  • Vinylogous acid
  • Tertiary alcohol
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Ketone
  • Organoheterocyclic compound
  • Acetal
  • Carboxylic acid derivative
  • Ether
  • Oxacycle
  • Polyol
  • Organofluoride
  • Organic oxide
  • Carbonyl group
  • Alcohol
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organohalogen compound
  • Hydrocarbon derivative
  • Alkyl halide
  • Alkyl fluoride
  • Primary alcohol
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.38 g/LALOGPS
logP1.46ALOGPS
logP0.015ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)-12ChemAxon
pKa (Strongest Basic)9.21ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area215.8 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity146.34 m³·mol⁻¹ChemAxon
Polarizability60.6 ųChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      details
      Abnormal Concentrations
      Not Available
      Associated Disorders and Diseases
      Disease ReferencesNone
      Associated OMIM IDsNone
      DrugBank IDNot Available
      DrugBank Metabolite IDDBMET00663
      Phenol Explorer Compound IDNot Available
      Phenol Explorer Metabolite IDNot Available
      FoodDB IDNot Available
      KNApSAcK IDNot Available
      Chemspider IDNot Available
      KEGG Compound IDNot Available
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      METLIN IDNot Available
      PubChem CompoundNot Available
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available