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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:15:29 UTC
Update Date2021-09-14 15:19:30 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
Data?1563866140
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
Description Belongs to the class of organic compounds known as aryl 1,2,4-triazolones. These are aromatic heterocyclic compounds containing a 1,2,4-triazolone moiety that is substituted at the 5-position with an aryl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzoles
Sub ClassTriazoles
Direct ParentAryl 1,2,4-triazolones
Alternative Parents
Substituents
  • Aryl 1,2,4-triazol-3-one
  • Triazolopyridine
  • Pyridinone
  • Pyridine
  • Heteroaromatic compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-290.51430932474
DeepCCS[M+Na]+264.28830932474
AllCCS[M+H]+262.932859911
AllCCS[M+H-H2O]+262.432859911
AllCCS[M+NH4]+263.532859911
AllCCS[M+Na]+263.632859911
AllCCS[M-H]-242.832859911
AllCCS[M+Na-2H]-247.632859911
AllCCS[M+HCOO]-253.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Desacetylvinblastine[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=C14997.2Standard polar33892256
Desacetylvinblastine[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=C14630.4Standard non polar33892256
Desacetylvinblastine[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=C15443.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Desacetylvinblastine,1TMS,isomer #1CC[C@]1(O[Si](C)(C)C)C[C@@H]2CN(CCC3=C([NH]C4=CC=CC=C34)[C@@](C(=O)OC)(C3=CC4=C(C=C3OC)N(C)[C@@H]3C45CCN4CC=C[C@](CC)([C@H]45)[C@@H](O)[C@]3(O)C(=O)OC)C2)C15617.2Semi standard non polar33892256
Desacetylvinblastine,1TMS,isomer #1CC[C@]1(O[Si](C)(C)C)C[C@@H]2CN(CCC3=C([NH]C4=CC=CC=C34)[C@@](C(=O)OC)(C3=CC4=C(C=C3OC)N(C)[C@@H]3C45CCN4CC=C[C@](CC)([C@H]45)[C@@H](O)[C@]3(O)C(=O)OC)C2)C15562.2Standard non polar33892256
Desacetylvinblastine,1TMS,isomer #1CC[C@]1(O[Si](C)(C)C)C[C@@H]2CN(CCC3=C([NH]C4=CC=CC=C34)[C@@](C(=O)OC)(C3=CC4=C(C=C3OC)N(C)[C@@H]3C45CCN4CC=C[C@](CC)([C@H]45)[C@@H](O)[C@]3(O)C(=O)OC)C2)C17787.8Standard polar33892256
Desacetylvinblastine,1TMS,isomer #2CC[C@]1(O)C[C@@H]2CN(CCC3=C([NH]C4=CC=CC=C34)[C@@](C(=O)OC)(C3=CC4=C(C=C3OC)N(C)[C@@H]3C45CCN4CC=C[C@](CC)([C@H]45)[C@@H](O[Si](C)(C)C)[C@]3(O)C(=O)OC)C2)C15626.9Semi standard non polar33892256
Desacetylvinblastine,1TMS,isomer #2CC[C@]1(O)C[C@@H]2CN(CCC3=C([NH]C4=CC=CC=C34)[C@@](C(=O)OC)(C3=CC4=C(C=C3OC)N(C)[C@@H]3C45CCN4CC=C[C@](CC)([C@H]45)[C@@H](O[Si](C)(C)C)[C@]3(O)C(=O)OC)C2)C15517.7Standard non polar33892256
Desacetylvinblastine,1TMS,isomer #2CC[C@]1(O)C[C@@H]2CN(CCC3=C([NH]C4=CC=CC=C34)[C@@](C(=O)OC)(C3=CC4=C(C=C3OC)N(C)[C@@H]3C45CCN4CC=C[C@](CC)([C@H]45)[C@@H](O[Si](C)(C)C)[C@]3(O)C(=O)OC)C2)C17597.5Standard polar33892256
Desacetylvinblastine,1TMS,isomer #3CC[C@]1(O)C[C@@H]2CN(CCC3=C([NH]C4=CC=CC=C34)[C@@](C(=O)OC)(C3=CC4=C(C=C3OC)N(C)[C@@H]3C45CCN4CC=C[C@](CC)([C@H]45)[C@@H](O)[C@]3(O[Si](C)(C)C)C(=O)OC)C2)C15632.9Semi standard non polar33892256
Desacetylvinblastine,1TMS,isomer #3CC[C@]1(O)C[C@@H]2CN(CCC3=C([NH]C4=CC=CC=C34)[C@@](C(=O)OC)(C3=CC4=C(C=C3OC)N(C)[C@@H]3C45CCN4CC=C[C@](CC)([C@H]45)[C@@H](O)[C@]3(O[Si](C)(C)C)C(=O)OC)C2)C15554.6Standard non polar33892256
Desacetylvinblastine,1TMS,isomer #3CC[C@]1(O)C[C@@H]2CN(CCC3=C([NH]C4=CC=CC=C34)[C@@](C(=O)OC)(C3=CC4=C(C=C3OC)N(C)[C@@H]3C45CCN4CC=C[C@](CC)([C@H]45)[C@@H](O)[C@]3(O[Si](C)(C)C)C(=O)OC)C2)C17718.7Standard polar33892256
Desacetylvinblastine,1TMS,isomer #4CC[C@]1(O)C[C@@H]2CN(CCC3=C(N([Si](C)(C)C)C4=CC=CC=C34)[C@@](C(=O)OC)(C3=CC4=C(C=C3OC)N(C)[C@@H]3C45CCN4CC=C[C@](CC)([C@H]45)[C@@H](O)[C@]3(O)C(=O)OC)C2)C15669.1Semi standard non polar33892256
Desacetylvinblastine,1TMS,isomer #4CC[C@]1(O)C[C@@H]2CN(CCC3=C(N([Si](C)(C)C)C4=CC=CC=C34)[C@@](C(=O)OC)(C3=CC4=C(C=C3OC)N(C)[C@@H]3C45CCN4CC=C[C@](CC)([C@H]45)[C@@H](O)[C@]3(O)C(=O)OC)C2)C15499.2Standard non polar33892256
Desacetylvinblastine,1TMS,isomer #4CC[C@]1(O)C[C@@H]2CN(CCC3=C(N([Si](C)(C)C)C4=CC=CC=C34)[C@@](C(=O)OC)(C3=CC4=C(C=C3OC)N(C)[C@@H]3C45CCN4CC=C[C@](CC)([C@H]45)[C@@H](O)[C@]3(O)C(=O)OC)C2)C17661.7Standard polar33892256
Desacetylvinblastine,1TBDMS,isomer #1CC[C@]1(O[Si](C)(C)C(C)(C)C)C[C@@H]2CN(CCC3=C([NH]C4=CC=CC=C34)[C@@](C(=O)OC)(C3=CC4=C(C=C3OC)N(C)[C@@H]3C45CCN4CC=C[C@](CC)([C@H]45)[C@@H](O)[C@]3(O)C(=O)OC)C2)C15807.5Semi standard non polar33892256
Desacetylvinblastine,1TBDMS,isomer #1CC[C@]1(O[Si](C)(C)C(C)(C)C)C[C@@H]2CN(CCC3=C([NH]C4=CC=CC=C34)[C@@](C(=O)OC)(C3=CC4=C(C=C3OC)N(C)[C@@H]3C45CCN4CC=C[C@](CC)([C@H]45)[C@@H](O)[C@]3(O)C(=O)OC)C2)C15780.4Standard non polar33892256
Desacetylvinblastine,1TBDMS,isomer #1CC[C@]1(O[Si](C)(C)C(C)(C)C)C[C@@H]2CN(CCC3=C([NH]C4=CC=CC=C34)[C@@](C(=O)OC)(C3=CC4=C(C=C3OC)N(C)[C@@H]3C45CCN4CC=C[C@](CC)([C@H]45)[C@@H](O)[C@]3(O)C(=O)OC)C2)C17819.7Standard polar33892256
Desacetylvinblastine,1TBDMS,isomer #2CC[C@]1(O)C[C@@H]2CN(CCC3=C([NH]C4=CC=CC=C34)[C@@](C(=O)OC)(C3=CC4=C(C=C3OC)N(C)[C@@H]3C45CCN4CC=C[C@](CC)([C@H]45)[C@@H](O[Si](C)(C)C(C)(C)C)[C@]3(O)C(=O)OC)C2)C15800.7Semi standard non polar33892256
Desacetylvinblastine,1TBDMS,isomer #2CC[C@]1(O)C[C@@H]2CN(CCC3=C([NH]C4=CC=CC=C34)[C@@](C(=O)OC)(C3=CC4=C(C=C3OC)N(C)[C@@H]3C45CCN4CC=C[C@](CC)([C@H]45)[C@@H](O[Si](C)(C)C(C)(C)C)[C@]3(O)C(=O)OC)C2)C15741.7Standard non polar33892256
Desacetylvinblastine,1TBDMS,isomer #2CC[C@]1(O)C[C@@H]2CN(CCC3=C([NH]C4=CC=CC=C34)[C@@](C(=O)OC)(C3=CC4=C(C=C3OC)N(C)[C@@H]3C45CCN4CC=C[C@](CC)([C@H]45)[C@@H](O[Si](C)(C)C(C)(C)C)[C@]3(O)C(=O)OC)C2)C17659.6Standard polar33892256
Desacetylvinblastine,1TBDMS,isomer #3CC[C@]1(O)C[C@@H]2CN(CCC3=C([NH]C4=CC=CC=C34)[C@@](C(=O)OC)(C3=CC4=C(C=C3OC)N(C)[C@@H]3C45CCN4CC=C[C@](CC)([C@H]45)[C@@H](O)[C@]3(O[Si](C)(C)C(C)(C)C)C(=O)OC)C2)C15825.0Semi standard non polar33892256
Desacetylvinblastine,1TBDMS,isomer #3CC[C@]1(O)C[C@@H]2CN(CCC3=C([NH]C4=CC=CC=C34)[C@@](C(=O)OC)(C3=CC4=C(C=C3OC)N(C)[C@@H]3C45CCN4CC=C[C@](CC)([C@H]45)[C@@H](O)[C@]3(O[Si](C)(C)C(C)(C)C)C(=O)OC)C2)C15785.4Standard non polar33892256
Desacetylvinblastine,1TBDMS,isomer #3CC[C@]1(O)C[C@@H]2CN(CCC3=C([NH]C4=CC=CC=C34)[C@@](C(=O)OC)(C3=CC4=C(C=C3OC)N(C)[C@@H]3C45CCN4CC=C[C@](CC)([C@H]45)[C@@H](O)[C@]3(O[Si](C)(C)C(C)(C)C)C(=O)OC)C2)C17769.5Standard polar33892256
Desacetylvinblastine,1TBDMS,isomer #4CC[C@]1(O)C[C@@H]2CN(CCC3=C(N([Si](C)(C)C(C)(C)C)C4=CC=CC=C34)[C@@](C(=O)OC)(C3=CC4=C(C=C3OC)N(C)[C@@H]3C45CCN4CC=C[C@](CC)([C@H]45)[C@@H](O)[C@]3(O)C(=O)OC)C2)C15791.9Semi standard non polar33892256
Desacetylvinblastine,1TBDMS,isomer #4CC[C@]1(O)C[C@@H]2CN(CCC3=C(N([Si](C)(C)C(C)(C)C)C4=CC=CC=C34)[C@@](C(=O)OC)(C3=CC4=C(C=C3OC)N(C)[C@@H]3C45CCN4CC=C[C@](CC)([C@H]45)[C@@H](O)[C@]3(O)C(=O)OC)C2)C15712.7Standard non polar33892256
Desacetylvinblastine,1TBDMS,isomer #4CC[C@]1(O)C[C@@H]2CN(CCC3=C(N([Si](C)(C)C(C)(C)C)C4=CC=CC=C34)[C@@](C(=O)OC)(C3=CC4=C(C=C3OC)N(C)[C@@H]3C45CCN4CC=C[C@](CC)([C@H]45)[C@@H](O)[C@]3(O)C(=O)OC)C2)C17700.8Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Desacetylvinblastine GC-MS (TMS_1_3) - 70eV, PositiveNot Available2022-08-08Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)Not Available2022-08-06Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Desacetylvinblastine 10V, Positive-QTOFsplash10-0uxr-0000001900-1677558d26cd95af761e2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Desacetylvinblastine 20V, Positive-QTOFsplash10-0uy3-0001004900-fcdc9b22c20c7034b1a82017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Desacetylvinblastine 40V, Positive-QTOFsplash10-0005-0001009100-8c0c6152602b69090a042017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Desacetylvinblastine 10V, Negative-QTOFsplash10-0a4i-0002004900-81e744eb13b1c6a4defe2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Desacetylvinblastine 20V, Negative-QTOFsplash10-052r-0019001100-771682a560b7e36e68d22017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Desacetylvinblastine 40V, Negative-QTOFsplash10-0zi4-0003009000-d060e004c26080acff2d2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Desacetylvinblastine 10V, Positive-QTOFsplash10-014i-0000000900-0941161bda19a6b265b52021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Desacetylvinblastine 20V, Positive-QTOFsplash10-0gb9-0000002900-bb7e145f61a4bee3abf22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Desacetylvinblastine 40V, Positive-QTOFsplash10-010d-0030108900-2e0140695bdfb5087f832021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Desacetylvinblastine 10V, Negative-QTOFsplash10-0ap1-0000005900-4b3c488ea17c49d624802021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Desacetylvinblastine 20V, Negative-QTOFsplash10-052e-0000009300-740993e5ba579b83df1d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Desacetylvinblastine 40V, Negative-QTOFsplash10-0006-0020009100-e5bb523bd88b743af6002021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
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 Compound71315532
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available