You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
StatusExpected but not Quantified
Creation Date2012-09-13 11:45:57 UTC
Update Date2019-07-23 06:35:10 UTC
Secondary Accession Numbers
  • HMDB41884
Metabolite Identification
Common NameDoxorubicinol
DescriptionDoxorubicinol, also known as adriamycinol or DOXOL, 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. Doxorubicinol is a very strong basic compound (based on its pKa). doxorubicinol can be biosynthesized from doxorubicin; which is catalyzed by the enzymes carbonyl reductase [nadph] 1, carbonyl reductase [nadph] 3, aldo-keto reductase family 1 member C3, and alcohol dehydrogenase [nadp(+)]. In humans, doxorubicinol is involved in doxorubicin metabolism pathway. These are polyketides containing a tetracenequinone ring structure with a sugar attached by glycosidic linkage.
Antibiotic 27706RpChEBI
Adriamycinol hydrochlorideHMDB
Adriamycinol, 8S-(8alpha,8R*,10alpha)-isomerHMDB
Chemical FormulaC27H31NO11
Average Molecular Weight545.5351
Monoisotopic Molecular Weight545.189710839
IUPAC Name(8S,10S)-10-{[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-8-[(1S)-1,2-dihydroxyethyl]-6,8,11-trihydroxy-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione
Traditional Name(8S,10S)-10-{[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-8-[(1S)-1,2-dihydroxyethyl]-6,8,11-trihydroxy-1-methoxy-9,10-dihydro-7H-tetracene-5,12-dione
CAS Registry Number54193-28-1
InChI Identifier
Chemical Taxonomy
Description 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
Sub ClassNot Available
Direct ParentAnthracyclines
Alternative Parents
  • Anthracycline
  • Anthracyclinone-skeleton
  • Aminoglycoside core
  • Tetracenequinone
  • 9,10-anthraquinone
  • 1,4-anthraquinone
  • Anthracene
  • Hexose monosaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Tetralin
  • Anisole
  • Aryl ketone
  • Alkyl aryl ether
  • Amino saccharide
  • Oxane
  • Benzenoid
  • Monosaccharide
  • Tertiary alcohol
  • Vinylogous acid
  • Secondary alcohol
  • 1,2-aminoalcohol
  • Ketone
  • Polyol
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Acetal
  • Alcohol
  • Primary alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Primary aliphatic amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available


Biological location:


Naturally occurring process:


Biological role:

Physical Properties
StateNot Available
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility1.49 g/LALOGPS
pKa (Strongest Acidic)9.74ChemAxon
pKa (Strongest Basic)9.14ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area209.23 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity135.36 m³·mol⁻¹ChemAxon
Polarizability55.18 ųChemAxon
Number of Rings5ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05cu-9202330000-293431fa9a3beabb905aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-05cr-9100027000-9c9cf29a2155532f09afSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0005590000-43113f22c78fca74fdebSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0329320000-a332c43d10c0b4ddb96dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4s-5109200000-ef48a2d5eeff5f4ea3e0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-1002290000-c9423b92582d5ee5ae84Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-016u-5207930000-fe3a4fe0aab942bc7aaaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-5208900000-fcd2c6340e9ee5713649Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Normal Concentrations
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      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 ID75768
      KEGG Compound IDNot Available
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      METLIN IDNot Available
      PubChem Compound83970
      PDB IDNot Available
      ChEBI ID133817
      Food Biomarker OntologyNot Available
      VMH IDNot Available
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General References
      1. van Asperen J, van Tellingen O, Tijssen F, Schinkel AH, Beijnen JH: Increased accumulation of doxorubicin and doxorubicinol in cardiac tissue of mice lacking mdr1a P-glycoprotein. Br J Cancer. 1999 Jan;79(1):108-13. [PubMed:10408701 ]
      2. Callies S, de Alwis DP, Wright JG, Sandler A, Burgess M, Aarons L: A population pharmacokinetic model for doxorubicin and doxorubicinol in the presence of a novel MDR modulator, zosuquidar trihydrochloride (LY335979). Cancer Chemother Pharmacol. 2003 Feb;51(2):107-18. Epub 2003 Jan 10. [PubMed:12647011 ]
      3. Bressolle F, Jacquet JM, Galtier M, Jourdan J, Donadio D, Rossi JF: Doxorubicin and doxorubicinol plasma concentrations and excretion in parotid saliva. Cancer Chemother Pharmacol. 1992;30(3):215-8. [PubMed:1628370 ]
      4. Salvatorelli E, Menna P, Cascegna S, Liberi G, Calafiore AM, Gianni L, Minotti G: Paclitaxel and docetaxel stimulation of doxorubicinol formation in the human heart: implications for cardiotoxicity of doxorubicin-taxane chemotherapies. J Pharmacol Exp Ther. 2006 Jul;318(1):424-33. Epub 2006 Apr 13. [PubMed:16614166 ]
      5. Eder AR, Chen JS, Arriaga EA: Separation of doxorubicin and doxorubicinol by cyclodextrin-modified micellar electrokinetic capillary chromatography. Electrophoresis. 2006 Aug;27(16):3263-70. [PubMed:16915573 ]
      6. Gilbert CM, Filippich LJ, McGeary RP, Charles BG: Pharmacokinetics of doxorubicinol in dogs. J Vet Pharmacol Ther. 2006 Oct;29(5):433-5. [PubMed:16958789 ]
      7. DiFrancesco R, Griggs JJ, Donnelly J, DiCenzo R: Simultaneous analysis of cyclophosphamide, doxorubicin and doxorubicinol by liquid chromatography coupled to tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2007 Jun 1;852(1-2):545-53. Epub 2007 Feb 24. [PubMed:17379584 ]
      8. Salvatorelli E, Menna P, Paz OG, Chello M, Covino E, Singer JW, Minotti G: The novel anthracenedione, pixantrone, lacks redox activity and inhibits doxorubicinol formation in human myocardium: insight to explain the cardiac safety of pixantrone in doxorubicin-treated patients. J Pharmacol Exp Ther. 2013 Feb;344(2):467-78. doi: 10.1124/jpet.112.200568. Epub 2012 Nov 28. [PubMed:23192654 ]
      9. Sottani C, Poggi G, Melchiorre F, Montagna B, Minoia C: Simultaneous measurement of doxorubicin and reduced metabolite doxorubicinol by UHPLC-MS/MS in human plasma of HCC patients treated with TACE. J Chromatogr B Analyt Technol Biomed Life Sci. 2013 Feb 1;915-916:71-8. doi: 10.1016/j.jchromb.2012.12.012. Epub 2012 Dec 22. [PubMed:23337906 ]
      10. Perez-Blanco JS, Fernandez de Gatta Mdel M, Hernandez-Rivas JM, Garcia Sanchez MJ, Sayalero Marinero ML, Gonzalez Lopez F: Validation and clinical evaluation of a UHPLC method with fluorescence detector for plasma quantification of doxorubicin and doxorubicinol in haematological patients. J Chromatogr B Analyt Technol Biomed Life Sci. 2014 Apr 1;955-956:93-7. doi: 10.1016/j.jchromb.2014.02.034. Epub 2014 Feb 28. [PubMed:24631816 ]
      11. Schaupp CM, White CC, Merrill GF, Kavanagh TJ: Metabolism of doxorubicin to the cardiotoxic metabolite doxorubicinol is increased in a mouse model of chronic glutathione deficiency: A potential role for carbonyl reductase 3. Chem Biol Interact. 2015 Jun 5;234:154-61. doi: 10.1016/j.cbi.2014.11.010. Epub 2014 Nov 21. [PubMed:25446851 ]
      12. Perez-Blanco JS, Santos-Buelga D, Fernandez de Gatta MD, Hernandez-Rivas JM, Martin A, Garcia MJ: Population pharmacokinetics of doxorubicin and doxorubicinol in patients diagnosed with non-Hodgkin's lymphoma. Br J Clin Pharmacol. 2016 Dec;82(6):1517-1527. doi: 10.1111/bcp.13070. Epub 2016 Sep 6. [PubMed:27447545 ]
      13. Lee HJ, Lee MG: Pharmacokinetics of adriamycin and adriamycinol after intravenous administration of adriamycin to rats with water-deprivation for 48 hours. Res Commun Mol Pathol Pharmacol. 1997 Jun;96(3):299-306. [PubMed:9261889 ]
      14. Fraier D, Frigerio E, Pianezzola E, Strolin Benedetti M, Cassidy J, Vasey P: A sensitive procedure for the quantitation of free and N-(2-hydroxypropyl) methacrylamide polymer-bound doxorubicin (PK1) and some of its metabolites, 13-dihydrodoxorubicin, 13-dihydrodoxorubicinone and doxorubicinone, in human plasma and urine by reversed-phase HPLC with fluorimetric detection. J Pharm Biomed Anal. 1995 Apr;13(4-5):625-33. [PubMed:9696578 ]
      15. de Bruijn P, Verweij J, Loos WJ, Kolker HJ, Planting AS, Nooter K, Stoter G, Sparreboom A: Determination of doxorubicin and doxorubicinol in plasma of cancer patients by high-performance liquid chromatography. Anal Biochem. 1999 Jan 15;266(2):216-21. [PubMed:9888978 ]