Hmdb loader
Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 08:09:52 UTC
Update Date2021-09-26 23:02:45 UTC
HMDB IDHMDB0251000
Secondary Accession NumbersNone
Metabolite Identification
Common NameN1,N11-Bis(ethyl)norspermine
DescriptionDiethylnorspermine belongs to the class of organic compounds known as dialkylamines. These are organic compounds containing a dialkylamine group, characterized by two alkyl groups bonded to the amino nitrogen. Based on a literature review a significant number of articles have been published on Diethylnorspermine. This compound has been identified in human blood as reported by (PMID: 31557052 ). N1,n11-bis(ethyl)norspermine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically N1,N11-Bis(ethyl)norspermine is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
Thumb
Synonyms
ValueSource
1,11-Bis(ethylamino)-4,8-diazaundecaneMeSH
BE 3-3-3MeSH
BE-3-3-3MeSH
BENSMMeSH
BENSpmMeSH
BESPMMeSH
N(1),N(11)-Bis(ethyl)norspermineMeSH
N(1),N(11)-DiethylnorspermineMeSH
N1,N11-Bis(ethyl)norspermineMeSH
Chemical FormulaC13H32N4
Average Molecular Weight244.427
Monoisotopic Molecular Weight244.262697046
IUPAC Name3,7,11,15-tetraazaheptadecane
Traditional Name3,7,11,15-tetraazaheptadecane
CAS Registry NumberNot Available
SMILES
CCNCCCNCCCNCCCNCC
InChI Identifier
InChI=1S/C13H32N4/c1-3-14-8-5-10-16-12-7-13-17-11-6-9-15-4-2/h14-17H,3-13H2,1-2H3
InChI KeyUMJJGDUYVQCBMC-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dialkylamines. These are organic compounds containing a dialkylamine group, characterized by two alkyl groups bonded to the amino nitrogen.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassAmines
Direct ParentDialkylamines
Alternative Parents
Substituents
  • Secondary aliphatic amine
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
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
logP0.77ALOGPS
logP-0.39ChemAxon
logS-3ALOGPS
pKa (Strongest Basic)10.75ChemAxon
Physiological Charge3ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area48.12 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity76.96 m³·mol⁻¹ChemAxon
Polarizability33.2 ųChemAxon
Number of Rings0ChemAxon
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]+159.25230932474
DeepCCS[M-H]-155.68930932474
DeepCCS[M-2H]-192.94230932474
DeepCCS[M+Na]+168.60530932474
AllCCS[M+H]+163.632859911
AllCCS[M+H-H2O]+160.732859911
AllCCS[M+NH4]+166.332859911
AllCCS[M+Na]+167.132859911
AllCCS[M-H]-163.132859911
AllCCS[M+Na-2H]-164.632859911
AllCCS[M+HCOO]-166.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N1,N11-Bis(ethyl)norspermineCCNCCCNCCCNCCCNCC2673.8Standard polar33892256
N1,N11-Bis(ethyl)norspermineCCNCCCNCCCNCCCNCC2195.3Standard non polar33892256
N1,N11-Bis(ethyl)norspermineCCNCCCNCCCNCCCNCC2034.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
N1,N11-Bis(ethyl)norspermine,1TMS,isomer #1CCNCCCNCCCNCCCN(CC)[Si](C)(C)C2237.0Semi standard non polar33892256
N1,N11-Bis(ethyl)norspermine,1TMS,isomer #1CCNCCCNCCCNCCCN(CC)[Si](C)(C)C2377.1Standard non polar33892256
N1,N11-Bis(ethyl)norspermine,1TMS,isomer #1CCNCCCNCCCNCCCN(CC)[Si](C)(C)C2835.0Standard polar33892256
N1,N11-Bis(ethyl)norspermine,1TMS,isomer #2CCNCCCNCCCN(CCCNCC)[Si](C)(C)C2143.7Semi standard non polar33892256
N1,N11-Bis(ethyl)norspermine,1TMS,isomer #2CCNCCCNCCCN(CCCNCC)[Si](C)(C)C2313.6Standard non polar33892256
N1,N11-Bis(ethyl)norspermine,1TMS,isomer #2CCNCCCNCCCN(CCCNCC)[Si](C)(C)C2811.7Standard polar33892256
N1,N11-Bis(ethyl)norspermine,2TMS,isomer #1CCN(CCCNCCCNCCCN(CC)[Si](C)(C)C)[Si](C)(C)C2389.1Semi standard non polar33892256
N1,N11-Bis(ethyl)norspermine,2TMS,isomer #1CCN(CCCNCCCNCCCN(CC)[Si](C)(C)C)[Si](C)(C)C2522.4Standard non polar33892256
N1,N11-Bis(ethyl)norspermine,2TMS,isomer #1CCN(CCCNCCCNCCCN(CC)[Si](C)(C)C)[Si](C)(C)C2601.7Standard polar33892256
N1,N11-Bis(ethyl)norspermine,2TMS,isomer #2CCNCCCN(CCCNCCCN(CC)[Si](C)(C)C)[Si](C)(C)C2292.4Semi standard non polar33892256
N1,N11-Bis(ethyl)norspermine,2TMS,isomer #2CCNCCCN(CCCNCCCN(CC)[Si](C)(C)C)[Si](C)(C)C2471.8Standard non polar33892256
N1,N11-Bis(ethyl)norspermine,2TMS,isomer #2CCNCCCN(CCCNCCCN(CC)[Si](C)(C)C)[Si](C)(C)C2593.0Standard polar33892256
N1,N11-Bis(ethyl)norspermine,2TMS,isomer #3CCNCCCNCCCN(CCCN(CC)[Si](C)(C)C)[Si](C)(C)C2304.6Semi standard non polar33892256
N1,N11-Bis(ethyl)norspermine,2TMS,isomer #3CCNCCCNCCCN(CCCN(CC)[Si](C)(C)C)[Si](C)(C)C2471.2Standard non polar33892256
N1,N11-Bis(ethyl)norspermine,2TMS,isomer #3CCNCCCNCCCN(CCCN(CC)[Si](C)(C)C)[Si](C)(C)C2608.8Standard polar33892256
N1,N11-Bis(ethyl)norspermine,2TMS,isomer #4CCNCCCN(CCCN(CCCNCC)[Si](C)(C)C)[Si](C)(C)C2231.5Semi standard non polar33892256
N1,N11-Bis(ethyl)norspermine,2TMS,isomer #4CCNCCCN(CCCN(CCCNCC)[Si](C)(C)C)[Si](C)(C)C2414.8Standard non polar33892256
N1,N11-Bis(ethyl)norspermine,2TMS,isomer #4CCNCCCN(CCCN(CCCNCC)[Si](C)(C)C)[Si](C)(C)C2597.9Standard polar33892256
N1,N11-Bis(ethyl)norspermine,3TMS,isomer #1CCN(CCCNCCCN(CCCN(CC)[Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2458.9Semi standard non polar33892256
N1,N11-Bis(ethyl)norspermine,3TMS,isomer #1CCN(CCCNCCCN(CCCN(CC)[Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2617.3Standard non polar33892256
N1,N11-Bis(ethyl)norspermine,3TMS,isomer #1CCN(CCCNCCCN(CCCN(CC)[Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2519.0Standard polar33892256
N1,N11-Bis(ethyl)norspermine,3TMS,isomer #2CCNCCCN(CCCN(CCCN(CC)[Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2381.9Semi standard non polar33892256
N1,N11-Bis(ethyl)norspermine,3TMS,isomer #2CCNCCCN(CCCN(CCCN(CC)[Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2592.6Standard non polar33892256
N1,N11-Bis(ethyl)norspermine,3TMS,isomer #2CCNCCCN(CCCN(CCCN(CC)[Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2525.6Standard polar33892256
N1,N11-Bis(ethyl)norspermine,4TMS,isomer #1CCN(CCCN(CCCN(CCCN(CC)[Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2561.8Semi standard non polar33892256
N1,N11-Bis(ethyl)norspermine,4TMS,isomer #1CCN(CCCN(CCCN(CCCN(CC)[Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2718.1Standard non polar33892256
N1,N11-Bis(ethyl)norspermine,4TMS,isomer #1CCN(CCCN(CCCN(CCCN(CC)[Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2449.4Standard polar33892256
N1,N11-Bis(ethyl)norspermine,1TBDMS,isomer #1CCNCCCNCCCNCCCN(CC)[Si](C)(C)C(C)(C)C2511.3Semi standard non polar33892256
N1,N11-Bis(ethyl)norspermine,1TBDMS,isomer #1CCNCCCNCCCNCCCN(CC)[Si](C)(C)C(C)(C)C2601.3Standard non polar33892256
N1,N11-Bis(ethyl)norspermine,1TBDMS,isomer #1CCNCCCNCCCNCCCN(CC)[Si](C)(C)C(C)(C)C2838.9Standard polar33892256
N1,N11-Bis(ethyl)norspermine,1TBDMS,isomer #2CCNCCCNCCCN(CCCNCC)[Si](C)(C)C(C)(C)C2420.1Semi standard non polar33892256
N1,N11-Bis(ethyl)norspermine,1TBDMS,isomer #2CCNCCCNCCCN(CCCNCC)[Si](C)(C)C(C)(C)C2534.5Standard non polar33892256
N1,N11-Bis(ethyl)norspermine,1TBDMS,isomer #2CCNCCCNCCCN(CCCNCC)[Si](C)(C)C(C)(C)C2814.0Standard polar33892256
N1,N11-Bis(ethyl)norspermine,2TBDMS,isomer #1CCN(CCCNCCCNCCCN(CC)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2870.5Semi standard non polar33892256
N1,N11-Bis(ethyl)norspermine,2TBDMS,isomer #1CCN(CCCNCCCNCCCN(CC)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2949.7Standard non polar33892256
N1,N11-Bis(ethyl)norspermine,2TBDMS,isomer #1CCN(CCCNCCCNCCCN(CC)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2727.7Standard polar33892256
N1,N11-Bis(ethyl)norspermine,2TBDMS,isomer #2CCNCCCN(CCCNCCCN(CC)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2784.6Semi standard non polar33892256
N1,N11-Bis(ethyl)norspermine,2TBDMS,isomer #2CCNCCCN(CCCNCCCN(CC)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2893.9Standard non polar33892256
N1,N11-Bis(ethyl)norspermine,2TBDMS,isomer #2CCNCCCN(CCCNCCCN(CC)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2722.9Standard polar33892256
N1,N11-Bis(ethyl)norspermine,2TBDMS,isomer #3CCNCCCNCCCN(CCCN(CC)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2809.6Semi standard non polar33892256
N1,N11-Bis(ethyl)norspermine,2TBDMS,isomer #3CCNCCCNCCCN(CCCN(CC)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2892.1Standard non polar33892256
N1,N11-Bis(ethyl)norspermine,2TBDMS,isomer #3CCNCCCNCCCN(CCCN(CC)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2731.2Standard polar33892256
N1,N11-Bis(ethyl)norspermine,2TBDMS,isomer #4CCNCCCN(CCCN(CCCNCC)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2746.5Semi standard non polar33892256
N1,N11-Bis(ethyl)norspermine,2TBDMS,isomer #4CCNCCCN(CCCN(CCCNCC)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2839.4Standard non polar33892256
N1,N11-Bis(ethyl)norspermine,2TBDMS,isomer #4CCNCCCN(CCCN(CCCNCC)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2724.9Standard polar33892256
N1,N11-Bis(ethyl)norspermine,3TBDMS,isomer #1CCN(CCCNCCCN(CCCN(CC)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3172.8Semi standard non polar33892256
N1,N11-Bis(ethyl)norspermine,3TBDMS,isomer #1CCN(CCCNCCCN(CCCN(CC)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3173.2Standard non polar33892256
N1,N11-Bis(ethyl)norspermine,3TBDMS,isomer #1CCN(CCCNCCCN(CCCN(CC)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2772.4Standard polar33892256
N1,N11-Bis(ethyl)norspermine,3TBDMS,isomer #2CCNCCCN(CCCN(CCCN(CC)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3141.2Semi standard non polar33892256
N1,N11-Bis(ethyl)norspermine,3TBDMS,isomer #2CCNCCCN(CCCN(CCCN(CC)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3122.9Standard non polar33892256
N1,N11-Bis(ethyl)norspermine,3TBDMS,isomer #2CCNCCCN(CCCN(CCCN(CC)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2776.0Standard polar33892256
N1,N11-Bis(ethyl)norspermine,4TBDMS,isomer #1CCN(CCCN(CCCN(CCCN(CC)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3507.8Semi standard non polar33892256
N1,N11-Bis(ethyl)norspermine,4TBDMS,isomer #1CCN(CCCN(CCCN(CCCN(CC)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3321.2Standard non polar33892256
N1,N11-Bis(ethyl)norspermine,4TBDMS,isomer #1CCN(CCCN(CCCN(CCCN(CC)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2810.8Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - N1,N11-Bis(ethyl)norspermine GC-MS (Non-derivatized) - 70eV, Positivesplash10-066r-7920000000-aacce0b6c70c333cff582017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N1,N11-Bis(ethyl)norspermine 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 - N1,N11-Bis(ethyl)norspermine 10V, Positive-QTOFsplash10-0002-2290000000-8bf1c9a5b61197faa5562017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N1,N11-Bis(ethyl)norspermine 20V, Positive-QTOFsplash10-000g-9430000000-a592512cda21b77964312017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N1,N11-Bis(ethyl)norspermine 40V, Positive-QTOFsplash10-002o-9200000000-a188c138f3c55e1f73982017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N1,N11-Bis(ethyl)norspermine 10V, Negative-QTOFsplash10-0006-0090000000-39d3d6433d9b1c1b307a2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N1,N11-Bis(ethyl)norspermine 20V, Negative-QTOFsplash10-0006-2390000000-c8d8ec98a9ab1052d5d22017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N1,N11-Bis(ethyl)norspermine 40V, Negative-QTOFsplash10-0006-9400000000-fc876f846296f031cd512017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N1,N11-Bis(ethyl)norspermine 10V, Positive-QTOFsplash10-0002-0090000000-bf9d59db0e343cadf1272021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N1,N11-Bis(ethyl)norspermine 20V, Positive-QTOFsplash10-0002-4190000000-c0f3b7c215d366f6d3b52021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N1,N11-Bis(ethyl)norspermine 40V, Positive-QTOFsplash10-0a4u-9200000000-b5dfb1bc25c2123b7aec2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N1,N11-Bis(ethyl)norspermine 10V, Negative-QTOFsplash10-0006-0090000000-a1c01259572ae485b4af2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N1,N11-Bis(ethyl)norspermine 20V, Negative-QTOFsplash10-0006-0190000000-03f8d7454a96bef21b942021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N1,N11-Bis(ethyl)norspermine 40V, Negative-QTOFsplash10-0006-9610000000-6a6bab7a8147f50f79c12021-10-12Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB06445
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4131
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
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 References
  1. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]