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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:12:04 UTC
Update Date2022-03-07 02:53:43 UTC
HMDB IDHMDB0033468
Secondary Accession Numbers
  • HMDB33468
Metabolite Identification
Common NameDiferuloylputrescine
DescriptionDiferuloylputrescine belongs to the class of organic compounds known as hydroxycinnamic acids and derivatives. Hydroxycinnamic acids and derivatives are compounds containing an cinnamic acid (or a derivative thereof) where the benzene ring is hydroxylated. Diferuloylputrescine has been detected, but not quantified in, a few different foods, such as fruits, garden tomatoes (Solanum lycopersicum), and pulses. This could make diferuloylputrescine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Diferuloylputrescine.
Structure
Data?1563862410
Synonyms
ValueSource
N,N'-bis(4-hydroxy-3-methoxycinnamoyl)-1,4-butanediamineHMDB
TerrestribisamideHMDB
trans-N,N'-diferuloylputrescineHMDB
(2E)-N-(4-{[(2E)-1-hydroxy-3-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-ylidene]amino}butyl)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enimidateGenerator
DiferuloylputrescineMeSH
Chemical FormulaC24H28N2O6
Average Molecular Weight440.4889
Monoisotopic Molecular Weight440.194736638
IUPAC Name(2E)-3-(4-hydroxy-3-methoxyphenyl)-N-{4-[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamido]butyl}prop-2-enamide
Traditional Name(E,E)-terrestribisamide
CAS Registry Number42369-86-8
SMILES
COC1=CC(\C=C\C(=O)NCCCCNC(=O)\C=C\C2=CC(OC)=C(O)C=C2)=CC=C1O
InChI Identifier
InChI=1S/C24H28N2O6/c1-31-21-15-17(5-9-19(21)27)7-11-23(29)25-13-3-4-14-26-24(30)12-8-18-6-10-20(28)22(16-18)32-2/h5-12,15-16,27-28H,3-4,13-14H2,1-2H3,(H,25,29)(H,26,30)/b11-7+,12-8+
InChI KeyCHEMZHJQHCVLFI-MKICQXMISA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxycinnamic acids and derivatives. Hydroxycinnamic acids and derivatives are compounds containing an cinnamic acid (or a derivative thereof) where the benzene ring is hydroxylated.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassHydroxycinnamic acids and derivatives
Direct ParentHydroxycinnamic acids and derivatives
Alternative Parents
Substituents
  • Cinnamic acid amide
  • Hydroxycinnamic acid or derivatives
  • Methoxyphenol
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Styrene
  • Phenol ether
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
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 Solubility0.0047 g/LALOGPS
logP2.67ALOGPS
logP2.59ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)9.59ChemAxon
pKa (Strongest Basic)1.82ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area117.12 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity123.99 m³·mol⁻¹ChemAxon
Polarizability48.87 ųChemAxon
Number of Rings2ChemAxon
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]+201.8230932474
DeepCCS[M-H]-199.46230932474
DeepCCS[M-2H]-232.97230932474
DeepCCS[M+Na]+208.38730932474
AllCCS[M+H]+207.432859911
AllCCS[M+H-H2O]+205.132859911
AllCCS[M+NH4]+209.532859911
AllCCS[M+Na]+210.132859911
AllCCS[M-H]-202.232859911
AllCCS[M+Na-2H]-203.332859911
AllCCS[M+HCOO]-204.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DiferuloylputrescineCOC1=CC(\C=C\C(=O)NCCCCNC(=O)\C=C\C2=CC(OC)=C(O)C=C2)=CC=C1O6443.5Standard polar33892256
DiferuloylputrescineCOC1=CC(\C=C\C(=O)NCCCCNC(=O)\C=C\C2=CC(OC)=C(O)C=C2)=CC=C1O4090.4Standard non polar33892256
DiferuloylputrescineCOC1=CC(\C=C\C(=O)NCCCCNC(=O)\C=C\C2=CC(OC)=C(O)C=C2)=CC=C1O4664.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Diferuloylputrescine,1TMS,isomer #1COC1=CC(/C=C/C(=O)NCCCCNC(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C(OC)=C2)=CC=C1O4427.8Semi standard non polar33892256
Diferuloylputrescine,1TMS,isomer #2COC1=CC(/C=C/C(=O)NCCCCN(C(=O)/C=C/C2=CC=C(O)C(OC)=C2)[Si](C)(C)C)=CC=C1O4395.9Semi standard non polar33892256
Diferuloylputrescine,2TMS,isomer #1COC1=CC(/C=C/C(=O)NCCCCNC(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C(OC)=C2)=CC=C1O[Si](C)(C)C4475.8Semi standard non polar33892256
Diferuloylputrescine,2TMS,isomer #2COC1=CC(/C=C/C(=O)N(CCCCNC(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C(OC)=C2)[Si](C)(C)C)=CC=C1O4397.4Semi standard non polar33892256
Diferuloylputrescine,2TMS,isomer #3COC1=CC(/C=C/C(=O)NCCCCN(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C(OC)=C2)[Si](C)(C)C)=CC=C1O4397.5Semi standard non polar33892256
Diferuloylputrescine,2TMS,isomer #4COC1=CC(/C=C/C(=O)N(CCCCN(C(=O)/C=C/C2=CC=C(O)C(OC)=C2)[Si](C)(C)C)[Si](C)(C)C)=CC=C1O4321.3Semi standard non polar33892256
Diferuloylputrescine,3TMS,isomer #1COC1=CC(/C=C/C(=O)NCCCCN(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C(OC)=C2)[Si](C)(C)C)=CC=C1O[Si](C)(C)C4404.9Semi standard non polar33892256
Diferuloylputrescine,3TMS,isomer #1COC1=CC(/C=C/C(=O)NCCCCN(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C(OC)=C2)[Si](C)(C)C)=CC=C1O[Si](C)(C)C4131.9Standard non polar33892256
Diferuloylputrescine,3TMS,isomer #2COC1=CC(/C=C/C(=O)N(CCCCN(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C(OC)=C2)[Si](C)(C)C)[Si](C)(C)C)=CC=C1O4312.5Semi standard non polar33892256
Diferuloylputrescine,3TMS,isomer #2COC1=CC(/C=C/C(=O)N(CCCCN(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C(OC)=C2)[Si](C)(C)C)[Si](C)(C)C)=CC=C1O4016.4Standard non polar33892256
Diferuloylputrescine,4TMS,isomer #1COC1=CC(/C=C/C(=O)N(CCCCN(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C(OC)=C2)[Si](C)(C)C)[Si](C)(C)C)=CC=C1O[Si](C)(C)C4351.6Semi standard non polar33892256
Diferuloylputrescine,4TMS,isomer #1COC1=CC(/C=C/C(=O)N(CCCCN(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C(OC)=C2)[Si](C)(C)C)[Si](C)(C)C)=CC=C1O[Si](C)(C)C3775.3Standard non polar33892256
Diferuloylputrescine,1TBDMS,isomer #1COC1=CC(/C=C/C(=O)NCCCCNC(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)=CC=C1O4690.9Semi standard non polar33892256
Diferuloylputrescine,1TBDMS,isomer #2COC1=CC(/C=C/C(=O)NCCCCN(C(=O)/C=C/C2=CC=C(O)C(OC)=C2)[Si](C)(C)C(C)(C)C)=CC=C1O4640.8Semi standard non polar33892256
Diferuloylputrescine,2TBDMS,isomer #1COC1=CC(/C=C/C(=O)NCCCCNC(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)=CC=C1O[Si](C)(C)C(C)(C)C4975.9Semi standard non polar33892256
Diferuloylputrescine,2TBDMS,isomer #2COC1=CC(/C=C/C(=O)N(CCCCNC(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)[Si](C)(C)C(C)(C)C)=CC=C1O4901.6Semi standard non polar33892256
Diferuloylputrescine,2TBDMS,isomer #3COC1=CC(/C=C/C(=O)NCCCCN(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)[Si](C)(C)C(C)(C)C)=CC=C1O4902.3Semi standard non polar33892256
Diferuloylputrescine,2TBDMS,isomer #4COC1=CC(/C=C/C(=O)N(CCCCN(C(=O)/C=C/C2=CC=C(O)C(OC)=C2)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O4779.4Semi standard non polar33892256
Diferuloylputrescine,3TBDMS,isomer #1COC1=CC(/C=C/C(=O)NCCCCN(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C5140.1Semi standard non polar33892256
Diferuloylputrescine,3TBDMS,isomer #1COC1=CC(/C=C/C(=O)NCCCCN(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C4663.9Standard non polar33892256
Diferuloylputrescine,3TBDMS,isomer #2COC1=CC(/C=C/C(=O)N(CCCCN(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O4994.3Semi standard non polar33892256
Diferuloylputrescine,3TBDMS,isomer #2COC1=CC(/C=C/C(=O)N(CCCCN(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O4454.0Standard non polar33892256
Diferuloylputrescine,4TBDMS,isomer #1COC1=CC(/C=C/C(=O)N(CCCCN(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C5195.5Semi standard non polar33892256
Diferuloylputrescine,4TBDMS,isomer #1COC1=CC(/C=C/C(=O)N(CCCCN(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C4296.3Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Diferuloylputrescine GC-MS (Non-derivatized) - 70eV, Positivesplash10-054k-1890000000-d437e9a00a5a2cb148b22017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Diferuloylputrescine GC-MS (2 TMS) - 70eV, Positivesplash10-0100-2092050000-f7807b409fcaa28a35962017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Diferuloylputrescine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Diferuloylputrescine 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 - Diferuloylputrescine 10V, Positive-QTOFsplash10-03dl-2290500000-8e676c8483a9c34c07a02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diferuloylputrescine 20V, Positive-QTOFsplash10-01p9-9460000000-4fd7d67f1f32a7aa7e0a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diferuloylputrescine 40V, Positive-QTOFsplash10-007a-9600000000-9d89d4c4b06259a7d6382016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diferuloylputrescine 10V, Negative-QTOFsplash10-000i-0210900000-546c6f9b9cf2fae55cf72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diferuloylputrescine 20V, Negative-QTOFsplash10-009l-0951800000-03e5629dd155a70f85292016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diferuloylputrescine 40V, Negative-QTOFsplash10-0006-3910000000-1f039896d35991177ed62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diferuloylputrescine 10V, Negative-QTOFsplash10-000i-0000900000-488d69889544a63fe3a22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diferuloylputrescine 20V, Negative-QTOFsplash10-000i-0942300000-7fc29dfed65c2d658d0d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diferuloylputrescine 40V, Negative-QTOFsplash10-01s9-0922000000-9033a171fe67972456ca2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diferuloylputrescine 10V, Positive-QTOFsplash10-0006-0000900000-67aee60ad648979ddce42021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diferuloylputrescine 20V, Positive-QTOFsplash10-0005-0931700000-609e4f01abde113152762021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diferuloylputrescine 40V, Positive-QTOFsplash10-002k-1904000000-c320845c05fd611059002021-09-23Wishart 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 IDFDB011510
KNApSAcK IDC00027843
Chemspider ID4479465
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5321825
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.. .