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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:11:08 UTC
Update Date2022-03-07 02:53:42 UTC
HMDB IDHMDB0033451
Secondary Accession Numbers
  • HMDB33451
Metabolite Identification
Common NameCadabicine
DescriptionCadabicine belongs to the class of organic compounds known as diarylethers. These are organic compounds containing the dialkyl ether functional group, with the formula ROR', where R and R' are aryl groups. Cadabicine is a very strong basic compound (based on its pKa). Outside of the human body, cadabicine has been detected, but not quantified in, fruits. This could make cadabicine a potential biomarker for the consumption of these foods.
Structure
Data?1563862408
SynonymsNot Available
Chemical FormulaC25H29N3O4
Average Molecular Weight435.524
Monoisotopic Molecular Weight435.215806426
IUPAC Name(8E,22E)-2-oxa-11,16,20-triazatricyclo[22.2.2.1³,⁷]nonacosa-1(26),3,5,7(29),8,10,20,22,24,27-decaene-4,10,21-triol
Traditional Name(8E,22E)-2-oxa-11,16,20-triazatricyclo[22.2.2.1³,⁷]nonacosa-1(26),3,5,7(29),8,10,20,22,24,27-decaene-4,10,21-triol
CAS Registry Number99964-83-7
SMILES
[H]\C1=C([H])\C(O)=NCCCNCCCCN=C(O)\C([H])=C([H])/C2=CC(OC3=CC=C1C=C3)=C(O)C=C2
InChI Identifier
InChI=1S/C25H29N3O4/c29-22-11-6-20-8-13-25(31)27-16-2-1-14-26-15-3-17-28-24(30)12-7-19-4-9-21(10-5-19)32-23(22)18-20/h4-13,18,26,29H,1-3,14-17H2,(H,27,31)(H,28,30)/b12-7-,13-8-
InChI KeyQBKGCCSZLPZTIE-AJDRMPRJSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as diarylethers. These are organic compounds containing the dialkyl ether functional group, with the formula ROR', where R and R' are aryl groups.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassEthers
Direct ParentDiarylethers
Alternative Parents
Substituents
  • Diaryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Cyclic carboximidic acid
  • Secondary aliphatic amine
  • Polyol
  • Secondary amine
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Organoheterocyclic compound
  • Oxacycle
  • Azacycle
  • Organic nitrogen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Amine
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point270 - 272 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0034 g/LALOGPS
logP3.42ALOGPS
logP0.65ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)4.74ChemAxon
pKa (Strongest Basic)10.66ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area106.67 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity127.9 m³·mol⁻¹ChemAxon
Polarizability46.79 ųChemAxon
Number of Rings3ChemAxon
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]+216.75130932474
DeepCCS[M-H]-214.35530932474
DeepCCS[M-2H]-247.23930932474
DeepCCS[M+Na]+222.66330932474
AllCCS[M+H]+205.532859911
AllCCS[M+H-H2O]+203.232859911
AllCCS[M+NH4]+207.632859911
AllCCS[M+Na]+208.132859911
AllCCS[M-H]-199.932859911
AllCCS[M+Na-2H]-200.632859911
AllCCS[M+HCOO]-201.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Cadabicine[H]\C1=C([H])\C(O)=NCCCNCCCCN=C(O)\C([H])=C([H])/C2=CC(OC3=CC=C1C=C3)=C(O)C=C26188.4Standard polar33892256
Cadabicine[H]\C1=C([H])\C(O)=NCCCNCCCCN=C(O)\C([H])=C([H])/C2=CC(OC3=CC=C1C=C3)=C(O)C=C23798.5Standard non polar33892256
Cadabicine[H]\C1=C([H])\C(O)=NCCCNCCCCN=C(O)\C([H])=C([H])/C2=CC(OC3=CC=C1C=C3)=C(O)C=C23913.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Cadabicine,1TMS,isomer #1C[Si](C)(C)OC1=NCCCNCCCCN=C(O)/C=C\C2=CC=C(O)C(=C2)OC2=CC=C(/C=C/1)C=C23901.5Semi standard non polar33892256
Cadabicine,1TMS,isomer #2C[Si](C)(C)OC1=NCCCCNCCCN=C(O)/C=C/C2=CC=C(C=C2)OC2=C(O)C=CC(=C2)/C=C\13894.9Semi standard non polar33892256
Cadabicine,1TMS,isomer #3C[Si](C)(C)OC1=CC=C2/C=C\C(O)=NCCCCNCCCN=C(O)/C=C/C3=CC=C(C=C3)OC1=C23894.3Semi standard non polar33892256
Cadabicine,1TMS,isomer #4C[Si](C)(C)N1CCCCN=C(O)/C=C\C2=CC=C(O)C(=C2)OC2=CC=C(/C=C/C(O)=NCCC1)C=C24039.8Semi standard non polar33892256
Cadabicine,2TMS,isomer #1C[Si](C)(C)OC1=NCCCCNCCCN=C(O[Si](C)(C)C)/C=C/C2=CC=C(C=C2)OC2=C(O)C=CC(=C2)/C=C\13966.7Semi standard non polar33892256
Cadabicine,2TMS,isomer #2C[Si](C)(C)OC1=NCCCNCCCCN=C(O)/C=C\C2=CC=C(O[Si](C)(C)C)C(=C2)OC2=CC=C(/C=C/1)C=C23903.1Semi standard non polar33892256
Cadabicine,2TMS,isomer #3C[Si](C)(C)OC1=NCCCN([Si](C)(C)C)CCCCN=C(O)/C=C\C2=CC=C(O)C(=C2)OC2=CC=C(/C=C/1)C=C23999.8Semi standard non polar33892256
Cadabicine,2TMS,isomer #4C[Si](C)(C)OC1=NCCCCNCCCN=C(O)/C=C/C2=CC=C(C=C2)OC2=C(O[Si](C)(C)C)C=CC(=C2)/C=C\13898.8Semi standard non polar33892256
Cadabicine,2TMS,isomer #5C[Si](C)(C)OC1=NCCCCN([Si](C)(C)C)CCCN=C(O)/C=C/C2=CC=C(C=C2)OC2=C(O)C=CC(=C2)/C=C\13998.4Semi standard non polar33892256
Cadabicine,2TMS,isomer #6C[Si](C)(C)OC1=CC=C2/C=C\C(O)=NCCCCN([Si](C)(C)C)CCCN=C(O)/C=C/C3=CC=C(C=C3)OC1=C24064.9Semi standard non polar33892256
Cadabicine,3TMS,isomer #1C[Si](C)(C)OC1=NCCCCNCCCN=C(O[Si](C)(C)C)/C=C/C2=CC=C(C=C2)OC2=C(O[Si](C)(C)C)C=CC(=C2)/C=C\13977.3Semi standard non polar33892256
Cadabicine,3TMS,isomer #2C[Si](C)(C)OC1=NCCCCN([Si](C)(C)C)CCCN=C(O[Si](C)(C)C)/C=C/C2=CC=C(C=C2)OC2=C(O)C=CC(=C2)/C=C\13996.0Semi standard non polar33892256
Cadabicine,3TMS,isomer #3C[Si](C)(C)OC1=NCCCN([Si](C)(C)C)CCCCN=C(O)/C=C\C2=CC=C(O[Si](C)(C)C)C(=C2)OC2=CC=C(/C=C/1)C=C24028.5Semi standard non polar33892256
Cadabicine,3TMS,isomer #4C[Si](C)(C)OC1=NCCCCN([Si](C)(C)C)CCCN=C(O)/C=C/C2=CC=C(C=C2)OC2=C(O[Si](C)(C)C)C=CC(=C2)/C=C\14025.1Semi standard non polar33892256
Cadabicine,4TMS,isomer #1C[Si](C)(C)OC1=NCCCCN([Si](C)(C)C)CCCN=C(O[Si](C)(C)C)/C=C/C2=CC=C(C=C2)OC2=C(O[Si](C)(C)C)C=CC(=C2)/C=C\14027.4Semi standard non polar33892256
Cadabicine,4TMS,isomer #1C[Si](C)(C)OC1=NCCCCN([Si](C)(C)C)CCCN=C(O[Si](C)(C)C)/C=C/C2=CC=C(C=C2)OC2=C(O[Si](C)(C)C)C=CC(=C2)/C=C\13575.2Standard non polar33892256
Cadabicine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=NCCCNCCCCN=C(O)/C=C\C2=CC=C(O)C(=C2)OC2=CC=C(/C=C/1)C=C24111.2Semi standard non polar33892256
Cadabicine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=NCCCCNCCCN=C(O)/C=C/C2=CC=C(C=C2)OC2=C(O)C=CC(=C2)/C=C\14104.4Semi standard non polar33892256
Cadabicine,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C2/C=C\C(O)=NCCCCNCCCN=C(O)/C=C/C3=CC=C(C=C3)OC1=C24129.6Semi standard non polar33892256
Cadabicine,1TBDMS,isomer #4CC(C)(C)[Si](C)(C)N1CCCCN=C(O)/C=C\C2=CC=C(O)C(=C2)OC2=CC=C(/C=C/C(O)=NCCC1)C=C24263.9Semi standard non polar33892256
Cadabicine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=NCCCCNCCCN=C(O[Si](C)(C)C(C)(C)C)/C=C/C2=CC=C(C=C2)OC2=C(O)C=CC(=C2)/C=C\14336.4Semi standard non polar33892256
Cadabicine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=NCCCNCCCCN=C(O)/C=C\C2=CC=C(O[Si](C)(C)C(C)(C)C)C(=C2)OC2=CC=C(/C=C/1)C=C24338.8Semi standard non polar33892256
Cadabicine,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=NCCCN([Si](C)(C)C(C)(C)C)CCCCN=C(O)/C=C\C2=CC=C(O)C(=C2)OC2=CC=C(/C=C/1)C=C24419.5Semi standard non polar33892256
Cadabicine,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC1=NCCCCNCCCN=C(O)/C=C/C2=CC=C(C=C2)OC2=C(O[Si](C)(C)C(C)(C)C)C=CC(=C2)/C=C\14334.6Semi standard non polar33892256
Cadabicine,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC1=NCCCCN([Si](C)(C)C(C)(C)C)CCCN=C(O)/C=C/C2=CC=C(C=C2)OC2=C(O)C=CC(=C2)/C=C\14423.0Semi standard non polar33892256
Cadabicine,2TBDMS,isomer #6CC(C)(C)[Si](C)(C)OC1=CC=C2/C=C\C(O)=NCCCCN([Si](C)(C)C(C)(C)C)CCCN=C(O)/C=C/C3=CC=C(C=C3)OC1=C24503.3Semi standard non polar33892256
Cadabicine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=NCCCCNCCCN=C(O[Si](C)(C)C(C)(C)C)/C=C/C2=CC=C(C=C2)OC2=C(O[Si](C)(C)C(C)(C)C)C=CC(=C2)/C=C\14497.7Semi standard non polar33892256
Cadabicine,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=NCCCCN([Si](C)(C)C(C)(C)C)CCCN=C(O[Si](C)(C)C(C)(C)C)/C=C/C2=CC=C(C=C2)OC2=C(O)C=CC(=C2)/C=C\14565.8Semi standard non polar33892256
Cadabicine,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=NCCCN([Si](C)(C)C(C)(C)C)CCCCN=C(O)/C=C\C2=CC=C(O[Si](C)(C)C(C)(C)C)C(=C2)OC2=CC=C(/C=C/1)C=C24646.9Semi standard non polar33892256
Cadabicine,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC1=NCCCCN([Si](C)(C)C(C)(C)C)CCCN=C(O)/C=C/C2=CC=C(C=C2)OC2=C(O[Si](C)(C)C(C)(C)C)C=CC(=C2)/C=C\14650.1Semi standard non polar33892256
Cadabicine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=NCCCCN([Si](C)(C)C(C)(C)C)CCCN=C(O[Si](C)(C)C(C)(C)C)/C=C/C2=CC=C(C=C2)OC2=C(O[Si](C)(C)C(C)(C)C)C=CC(=C2)/C=C\14736.8Semi standard non polar33892256
Cadabicine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=NCCCCN([Si](C)(C)C(C)(C)C)CCCN=C(O[Si](C)(C)C(C)(C)C)/C=C/C2=CC=C(C=C2)OC2=C(O[Si](C)(C)C(C)(C)C)C=CC(=C2)/C=C\14120.1Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Cadabicine GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-0001900000-8b4f141b2ac02a14d7ae2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cadabicine GC-MS (3 TMS) - 70eV, Positivesplash10-00bi-8000094000-c54dd48fd55fa2df8c752017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cadabicine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cadabicine 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 - Cadabicine 10V, Positive-QTOFsplash10-000i-0000900000-f776fb3ed46a5b2eb7d82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cadabicine 20V, Positive-QTOFsplash10-00kr-0000900000-e9cf6578d54d16c178a22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cadabicine 40V, Positive-QTOFsplash10-0gb9-0002900000-92d9909036a0c2dfb9c62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cadabicine 10V, Negative-QTOFsplash10-001i-0000900000-def78ab20a7c351f1f0b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cadabicine 20V, Negative-QTOFsplash10-00lr-0000900000-903593ca99371dcd4ef32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cadabicine 40V, Negative-QTOFsplash10-014l-2007900000-d7642669bed77e6e72f52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cadabicine 10V, Positive-QTOFsplash10-000i-0000900000-1d0314d1e0150f031b602021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cadabicine 20V, Positive-QTOFsplash10-000i-0000900000-453dd655f0d4015f30f12021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cadabicine 40V, Positive-QTOFsplash10-0gkl-0009700000-60f10d9f0b3f534036c62021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cadabicine 10V, Negative-QTOFsplash10-00lr-0000900000-844623584104ec07987b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cadabicine 20V, Negative-QTOFsplash10-001i-0001900000-881e0d3e5e23bcf3526e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cadabicine 40V, Negative-QTOFsplash10-00bl-0009100000-0e87806e5b547c9aa5512021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB011489
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
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. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .