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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:45:57 UTC
Update Date2017-12-07 04:29:19 UTC
HMDB IDHMDB0041884
Secondary Accession Numbers
  • HMDB41884
Metabolite Identification
Common NameDoxorubicinol
DescriptionDoxorubicinol belongs to the family of Anthracyclines. These are polyketides containing a tetracenequinone ring structure with a sugar attached by glycosidic linkage.
Structure
Thumb
Synonyms
ValueSource
Adriamycinol hydrochlorideMeSH
13-DihydrodoxorubicinMeSH
AdriamycinolMeSH
Adriamycinol, 8S-(8alpha,8R*,10alpha)-isomerMeSH
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
SMILES
COC1=CC=CC2=C1C(=O)C1=C(C(O)=C3C[C@](O)(C[C@H](O[C@H]4C[C@H](N)[C@H](O)[C@H](C)O4)C3=C1O)[C@@H](O)CO)C2=O
InChI Identifier
InChI=1S/C27H31NO11/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/h3-5,10,13,15-17,22,29-31,33,35-36H,6-9,28H2,1-2H3/t10-,13-,15-,16-,17-,22+,27-/m0/s1
InChI KeyNKZRZOVSJNSBFR-FEMMEMONSA-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
  • 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
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

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
logP0.35ALOGPS
logP0.23ChemAxon
logS-2.6ALOGPS
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
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05cu-9202330000-293431fa9a3beabb905aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-05cr-9100027000-9c9cf29a2155532f09afView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0005590000-43113f22c78fca74fdebView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0329320000-a332c43d10c0b4ddb96dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4s-5109200000-ef48a2d5eeff5f4ea3e0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-1002290000-c9423b92582d5ee5ae84View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-016u-5207930000-fe3a4fe0aab942bc7aaaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-5208900000-fcd2c6340e9ee5713649View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways
NameSMPDB/PathwhizKEGG
Doxorubicin Metabolism PathwayPw000626Pw000626 greyscalePw000626 simpleNot Available
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 IDDBMET00647
      Phenol Explorer Compound IDNot Available
      Phenol Explorer Metabolite 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
      References
      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 ]