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Record Information
Version4.0
Creation Date2013-07-09 16:15:29 UTC
Update Date2017-09-27 08:44:00 UTC
HMDB IDHMDB0061054
Secondary Accession Numbers
  • HMDB61054
Metabolite Identification
Common NameDesacetylvinblastine
DescriptionDesacetylvinblastine is a metabolite of vinblastine. Vinblastine is an antimicrotubule drug used to treat certain kinds of cancer, including Hodgkin's lymphoma, non-small cell lung cancer, breast cancer, head and neck cancer, and testicular cancer. It is also used to treat Langerhans cell histiocytosis. Vinblastine was traditionally obtained from Catharanthus roseus, also known as Vinca rosea, a Madagascar Periwinkle. It is generated in the plant by the joining of two alkaloids catharanthine and vindoline. (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC44H56N4O8
Average Molecular Weight768.9374
Monoisotopic Molecular Weight768.409814788
IUPAC Namemethyl (9R,10S,11R,12R,19R)-12-ethyl-4-[(13S,15R,17S)-17-ethyl-17-hydroxy-13-(methoxycarbonyl)-1,11-diazatetracyclo[13.3.1.0⁴,¹².0⁵,¹⁰]nonadeca-4(12),5,7,9-tetraen-13-yl]-10,11-dihydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6,13-tetraene-10-carboxylate
Traditional Namemethyl (9R,10S,11R,12R,19R)-12-ethyl-4-[(13S,15R,17S)-17-ethyl-17-hydroxy-13-(methoxycarbonyl)-1,11-diazatetracyclo[13.3.1.0⁴,¹².0⁵,¹⁰]nonadeca-4(12),5,7,9-tetraen-13-yl]-10,11-dihydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6,13-tetraene-10-carboxylate
CAS Registry NumberNot Available
SMILES
[H][C@]12CN(C[C@](O)(CC)C1)CCC1=C(NC3=CC=CC=C13)[C@@](C2)(C(=O)OC)C1=C(OC)C=C2N(C)[C@@H]3C4(CCN5CC=C[C@](CC)([C@@H]45)[C@@H](O)[C@]3(O)C(=O)OC)C2=C1
InChI Identifier
InChI=1S/C44H56N4O8/c1-7-40(52)22-26-23-43(38(50)55-5,34-28(14-18-47(24-26)25-40)27-12-9-10-13-31(27)45-34)30-20-29-32(21-33(30)54-4)46(3)36-42(29)16-19-48-17-11-15-41(8-2,35(42)48)37(49)44(36,53)39(51)56-6/h9-13,15,20-21,26,35-37,45,49,52-53H,7-8,14,16-19,22-25H2,1-6H3/t26-,35-,36+,37+,40-,41+,42?,43-,44-/m0/s1
InChI KeyNDMPLJNOPCLANR-CYJJREDESA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as vinca alkaloids. These are alkaloids with a dimeric chemical structure composed of an indole nucleus (catharanthine), and a dihydroindole nucleus (vindoline), joined together.
KingdomChemical entities
Super ClassOrganic compounds
ClassAlkaloids and derivatives
Sub ClassVinca alkaloids
Direct ParentVinca alkaloids
Alternative Parents
Substituents
  • Vinca alkaloid skeleton
  • Carbazole
  • 3-alkylindole
  • Indole
  • Indole or derivatives
  • Anisole
  • Dialkylarylamine
  • Tertiary aliphatic/aromatic amine
  • Alkyl aryl ether
  • Beta-hydroxy acid
  • Aralkylamine
  • Dicarboxylic acid or derivatives
  • Hydroxy acid
  • Benzenoid
  • N-alkylpyrrolidine
  • Piperidine
  • Cyclic alcohol
  • Heteroaromatic compound
  • Methyl ester
  • Pyrrole
  • Pyrrolidine
  • Tertiary alcohol
  • Tertiary amine
  • Tertiary aliphatic amine
  • Secondary alcohol
  • Amino acid or derivatives
  • 1,2-aminoalcohol
  • Carboxylic acid ester
  • Organoheterocyclic compound
  • Azacycle
  • Ether
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Amine
  • Alcohol
  • Organonitrogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

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 Solubility0.055 g/LALOGPS
logP3.65ALOGPS
logP3.74ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)10.9ChemAxon
pKa (Strongest Basic)8.75ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area148.03 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity213.27 m³·mol⁻¹ChemAxon
Polarizability83.5 ųChemAxon
Number of Rings9ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways
NameSMPDB/PathwhizKEGG
Vinblastine PathwayPw000241Pw000241 greyscalePw000241 simpleNot Available
Displaying 1 entry
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 IDDBMET00398
      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
      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