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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-07-04 19:01:48 UTC
Update Date2018-05-20 20:30:11 UTC
HMDB IDHMDB0060822
Secondary Accession Numbers
  • HMDB60822
Metabolite Identification
Common NameDoxorubicin-semiquinone
DescriptionDoxorubicin-semiquinone is a metabolite of doxorubicin. Doxorubicin is a drug used in cancer chemotherapy. It is an anthracycline antibiotic, closely related to the natural product daunomycin, and like all anthracyclines, it works by intercalating DNA. Doxorubicin is commonly used in the treatment of a wide range of cancers, including hematological malignancies, many types of carcinoma, and soft tissue sarcomas. Doxorubicin's most serious adverse effect is life-threatening heart damage. (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC27H33NO11
Average Molecular Weight547.557
Monoisotopic Molecular Weight547.205360887
IUPAC Name1-{4-[(4-amino-5-hydroxy-6-methyloxan-2-yl)oxy]-2,5,6,11,12-pentahydroxy-7-methoxy-1,2,3,4,6,11-hexahydrotetracen-2-yl}-2-hydroxyethan-1-one
Traditional Name1-{4-[(4-amino-5-hydroxy-6-methyloxan-2-yl)oxy]-2,5,6,11,12-pentahydroxy-7-methoxy-3,4,6,11-tetrahydro-1H-tetracen-2-yl}-2-hydroxyethanone
CAS Registry NumberNot Available
SMILES
COC1=CC=CC2=C1C(O)C1=C(C2O)C(O)=C2CC(O)(CC(OC3CC(N)C(O)C(C)O3)C2=C1O)C(=O)CO
InChI Identifier
InChI=1S/C27H33NO11/c1-10-22(31)13(28)6-17(38-10)39-15-8-27(36,16(30)9-29)7-12-19(15)26(35)21-20(24(12)33)23(32)11-4-3-5-14(37-2)18(11)25(21)34/h3-5,10,13,15,17,22-23,25,29,31-36H,6-9,28H2,1-2H3
InChI KeyWHLRWGKIZVSENZ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as aminoglycosides. These are molecules or a portion of a molecule composed of amino-modified sugars.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentAminoglycosides
Alternative Parents
Substituents
  • Aminoglycoside core
  • Anthracene
  • Hexose monosaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Tetralin
  • Anisole
  • Alkyl aryl ether
  • Monosaccharide
  • Benzenoid
  • Oxane
  • Tertiary alcohol
  • Alpha-hydroxy ketone
  • Secondary alcohol
  • Ketone
  • 1,2-aminoalcohol
  • Polyol
  • Ether
  • Oxacycle
  • Organoheterocyclic compound
  • Acetal
  • Primary alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Amine
  • Primary amine
  • Organic nitrogen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

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 Solubility1.49 g/LALOGPS
logP-0.47ALOGPS
logP-1.4ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)9.11ChemAxon
pKa (Strongest Basic)11.24ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area212.39 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity135.64 m³·mol⁻¹ChemAxon
Polarizability56.53 ųChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
      Phenol Explorer Compound 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 Compound131769967
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available