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Record Information
Version3.6
Creation Date2013-06-15 17:09:54 UTC
Update Date2016-02-11 08:08:48 UTC
HMDB IDHMDB60586
Secondary Accession NumbersNone
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
SynonymsNot Available
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=1/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 KeyInChIKey=TWMWXCYMYAQOTO-UHFFFAOYNA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as anthracyclines. These are polyketides containing a tetracenequinone ring structure with a sugar attached by glycosidic linkage.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassAnthracyclines
Sub ClassNot Available
Direct ParentAnthracyclines
Alternative Parents
Substituents
  • Anthracyclinone-skeleton
  • Anthracycline
  • Tetracenequinone
  • 1,4-anthraquinone
  • 9,10-anthraquinone
  • Anthracene
  • Amino sugar
  • Tetralin
  • Aryl ketone
  • Hydroquinone
  • Anisole
  • Amino saccharide
  • Alkyl aryl ether
  • Benzenoid
  • Oxane
  • Monosaccharide
  • Saccharide
  • Vinylogous acid
  • Tertiary alcohol
  • Secondary alcohol
  • Polyol
  • Ketone
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Ether
  • Carboximidic acid derivative
  • Carboximidic acid
  • Acetal
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organofluoride
  • Organohalogen compound
  • Alkyl halide
  • Alkyl fluoride
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug metabolite
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity146.34 m3·mol-1ChemAxon
Polarizability60.6 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
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
NuGOwiki LinkHMDB60586
Metagene LinkHMDB60586
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