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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2022-03-07 02:51:36 UTC
HMDB IDHMDB0014381
Secondary Accession Numbers
  • HMDB14381
Metabolite Identification
Common NamePipobroman
DescriptionPipobroman, also known as vercyte or a 8103, belongs to the class of organic compounds known as piperazines. Piperazines are compounds containing a piperazine ring, which is a saturated aliphatic six-member heterocyclic with two nitrogen atoms at positions 1 and 4, as well as four carbon atoms. Pipobroman is a drug which is used for the treatment of polycythaemia vera and refractory chronic myeloid leukaemia. Based on a literature review a significant number of articles have been published on Pipobroman.
Structure
Data?1582753172
Synonyms
ValueSource
1,4-Bis(3-bromopropionyl)piperazineChEBI
a 8103ChEBI
a-8103ChEBI
AmedelChEBI
N,N-Bis-(3-bromopropionyl)-piperazineChEBI
VercyteChEBI
Chemical FormulaC10H16Br2N2O2
Average Molecular Weight356.054
Monoisotopic Molecular Weight353.95785306
IUPAC Name3-bromo-1-[4-(3-bromopropanoyl)piperazin-1-yl]propan-1-one
Traditional Namepipobroman
CAS Registry Number54-91-1
SMILES
BrCCC(=O)N1CCN(CC1)C(=O)CCBr
InChI Identifier
InChI=1S/C10H16Br2N2O2/c11-3-1-9(15)13-5-7-14(8-6-13)10(16)2-4-12/h1-8H2
InChI KeyNJBFOOCLYDNZJN-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as piperazines. Piperazines are compounds containing a piperazine ring, which is a saturated aliphatic six-member heterocyclic with two nitrogen atoms at positions 1 and 4, as well as four carbon atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazinanes
Sub ClassPiperazines
Direct ParentPiperazines
Alternative Parents
Substituents
  • Piperazine
  • Tertiary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid derivative
  • Azacycle
  • Alkyl bromide
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organobromide
  • Organohalogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Alkyl halide
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point> 300 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility2.24 g/LNot Available
LogP1.1Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility2.24 g/LALOGPS
logP1.09ALOGPS
logP0.41ChemAxon
logS-2.2ALOGPS
pKa (Strongest Basic)-0.72ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area40.62 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity69.45 m³·mol⁻¹ChemAxon
Polarizability28.44 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+154.26130932474
DeepCCS[M-H]-151.90330932474
DeepCCS[M-2H]-185.86930932474
DeepCCS[M+Na]+160.83330932474
AllCCS[M+H]+166.632859911
AllCCS[M+H-H2O]+163.932859911
AllCCS[M+NH4]+169.232859911
AllCCS[M+Na]+169.932859911
AllCCS[M-H]-164.932859911
AllCCS[M+Na-2H]-166.232859911
AllCCS[M+HCOO]-167.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PipobromanBrCCC(=O)N1CCN(CC1)C(=O)CCBr2673.3Standard polar33892256
PipobromanBrCCC(=O)N1CCN(CC1)C(=O)CCBr1961.8Standard non polar33892256
PipobromanBrCCC(=O)N1CCN(CC1)C(=O)CCBr2588.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Pipobroman GC-MS (Non-derivatized) - 70eV, Positivesplash10-056r-3980000000-8bd279e69119d9648d5b2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pipobroman GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pipobroman GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pipobroman 10V, Positive-QTOFsplash10-0udi-0139000000-aa4921fbff3c003c871f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pipobroman 20V, Positive-QTOFsplash10-0ul0-4968000000-94fcf9b74b69619540e92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pipobroman 40V, Positive-QTOFsplash10-000i-9610000000-02d07b217917ecfc91e72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pipobroman 10V, Negative-QTOFsplash10-0udi-0129000000-23f3440e6b284425653f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pipobroman 20V, Negative-QTOFsplash10-0uxr-0696000000-8158a82dd2fe379c501f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pipobroman 40V, Negative-QTOFsplash10-01qi-7920000000-ab7db93bf44290624bec2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pipobroman 10V, Negative-QTOFsplash10-014i-1793000000-3de2c8d6716323b5962b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pipobroman 20V, Negative-QTOFsplash10-00or-5892000000-9b2a25a7697cd7a2a25f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pipobroman 40V, Negative-QTOFsplash10-004i-9000000000-28b4ae48a39b48af6c7d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pipobroman 10V, Positive-QTOFsplash10-0udi-0009000000-4265af251f045bf888192021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pipobroman 20V, Positive-QTOFsplash10-0udi-0029000000-2a422250aab165cd7b1c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pipobroman 40V, Positive-QTOFsplash10-0006-9610000000-0cf247041481b787196c2021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00236 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00236 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00236
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4676
KEGG Compound IDC07362
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPipobroman
METLIN IDNot Available
PubChem Compound4842
PDB IDNot Available
ChEBI ID8242
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