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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-07-04 19:01:48 UTC
Update Date2019-07-23 07:15:10 UTC
HMDB IDHMDB0060822
Secondary Accession Numbers
  • HMDB60822
Metabolite Identification
Common NameDoxorubicin-semiquinone
DescriptionDoxorubicin-semiquinone belongs to the class of organic compounds known as aminoglycosides. These are molecules or a portion of a molecule composed of amino-modified sugars. Doxorubicin-semiquinone is a very strong basic compound (based on its pKa). Within humans, doxorubicin-semiquinone participates in a number of enzymatic reactions. In particular, doxorubicin-semiquinone can be biosynthesized from doxorubicin through its interaction with the enzymes nitric-oxide synthase, endothelial, xanthine dehydrogenase/oxidase, and nad(p)H dehydrogenase [quinone] 1. In addition, doxorubicin-semiquinone can be biosynthesized from doxorubicin through its interaction with the enzymes nadh dehydrogenase [ubiquinone] iron-sulfur protein 2, mitochondrial, nadh dehydrogenase [ubiquinone] iron-sulfur protein 3, mitochondrial, and nadh dehydrogenase [ubiquinone] iron-sulfur protein 7, mitochondrial. In humans, doxorubicin-semiquinone is involved in doxorubicin metabolism pathway. Doxorubicin's most serious adverse effect is life-threatening heart damage. 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 is a drug used in cancer chemotherapy. Doxorubicin-semiquinone is a metabolite of doxorubicin. It is an anthracycline antibiotic, closely related to the natural product daunomycin, and like all anthracyclines, it works by intercalating DNA.
Structure
Data?1563866110
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f8a-0002790000-a8c108c699377e348c31Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uyi-0423920000-dbf9166be0865fe36806Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pc0-7229600000-f8c2348d1003a9460e7dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0002390000-3b667c382d89aa8dc35bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0694-4208950000-9a77c1cf22c05b9462b5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0670-5205910000-1ddd35a53c9a33bd3c95Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available