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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:11:57 UTC
Update Date2022-03-07 02:53:43 UTC
HMDB IDHMDB0033466
Secondary Accession Numbers
  • HMDB33466
Metabolite Identification
Common NameDi-4-coumaroylputrescine
DescriptionDi-4-coumaroylputrescine belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. Di-4-coumaroylputrescine has been detected, but not quantified in, several different foods, such as fats and oils, fruits, pomes, pulses, and red raspberries (Rubus idaeus). This could make di-4-coumaroylputrescine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Di-4-coumaroylputrescine.
Structure
Data?1563862410
Synonyms
ValueSource
N,N'-1,4-butanediylbis[3-(4-hydroxyphenyl)-2-propenamide], 9ciHMDB
N,N'-bis(4-hydroxycinnamoyl)-1,4-butanediamineHMDB
(2E)-N-(4-{[(2E)-1-hydroxy-3-(4-hydroxyphenyl)prop-2-en-1-ylidene]amino}butyl)-3-(4-hydroxyphenyl)prop-2-enimidateGenerator
Chemical FormulaC22H24N2O4
Average Molecular Weight380.437
Monoisotopic Molecular Weight380.173607266
IUPAC Name(2E)-3-(4-hydroxyphenyl)-N-{4-[(2E)-3-(4-hydroxyphenyl)prop-2-enamido]butyl}prop-2-enamide
Traditional Name(2E)-3-(4-hydroxyphenyl)-N-{4-[(2E)-3-(4-hydroxyphenyl)prop-2-enamido]butyl}prop-2-enamide
CAS Registry Number37946-59-1
SMILES
OC1=CC=C(\C=C\C(=O)NCCCCNC(=O)\C=C\C2=CC=C(O)C=C2)C=C1
InChI Identifier
InChI=1S/C22H24N2O4/c25-19-9-3-17(4-10-19)7-13-21(27)23-15-1-2-16-24-22(28)14-8-18-5-11-20(26)12-6-18/h3-14,25-26H,1-2,15-16H2,(H,23,27)(H,24,28)/b13-7+,14-8+
InChI KeyPYVBFDCHJDMSMM-FNCQTZNRSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassHydroxycinnamic acids and derivatives
Direct ParentCoumaric acids and derivatives
Alternative Parents
Substituents
  • Cinnamic acid amide
  • Coumaric acid or derivatives
  • Styrene
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • 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 Solubility182 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0042 g/LALOGPS
logP2.74ALOGPS
logP2.9ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)9.12ChemAxon
pKa (Strongest Basic)1.82ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area98.66 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity111.06 m³·mol⁻¹ChemAxon
Polarizability42.98 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]+194.77630932474
DeepCCS[M-H]-192.41930932474
DeepCCS[M-2H]-226.17330932474
DeepCCS[M+Na]+201.52130932474
AllCCS[M+H]+191.832859911
AllCCS[M+H-H2O]+189.132859911
AllCCS[M+NH4]+194.232859911
AllCCS[M+Na]+194.932859911
AllCCS[M-H]-190.432859911
AllCCS[M+Na-2H]-191.032859911
AllCCS[M+HCOO]-191.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Di-4-coumaroylputrescineOC1=CC=C(\C=C\C(=O)NCCCCNC(=O)\C=C\C2=CC=C(O)C=C2)C=C15618.3Standard polar33892256
Di-4-coumaroylputrescineOC1=CC=C(\C=C\C(=O)NCCCCNC(=O)\C=C\C2=CC=C(O)C=C2)C=C13190.2Standard non polar33892256
Di-4-coumaroylputrescineOC1=CC=C(\C=C\C(=O)NCCCCNC(=O)\C=C\C2=CC=C(O)C=C2)C=C14413.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Di-4-coumaroylputrescine,1TMS,isomer #1C[Si](C)(C)OC1=CC=C(/C=C/C(=O)NCCCCNC(=O)/C=C/C2=CC=C(O)C=C2)C=C14079.1Semi standard non polar33892256
Di-4-coumaroylputrescine,1TMS,isomer #2C[Si](C)(C)N(CCCCNC(=O)/C=C/C1=CC=C(O)C=C1)C(=O)/C=C/C1=CC=C(O)C=C14069.2Semi standard non polar33892256
Di-4-coumaroylputrescine,2TMS,isomer #1C[Si](C)(C)OC1=CC=C(/C=C/C(=O)NCCCCNC(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C=C2)C=C14160.5Semi standard non polar33892256
Di-4-coumaroylputrescine,2TMS,isomer #2C[Si](C)(C)OC1=CC=C(/C=C/C(=O)N(CCCCNC(=O)/C=C/C2=CC=C(O)C=C2)[Si](C)(C)C)C=C14109.3Semi standard non polar33892256
Di-4-coumaroylputrescine,2TMS,isomer #3C[Si](C)(C)OC1=CC=C(/C=C/C(=O)NCCCCN(C(=O)/C=C/C2=CC=C(O)C=C2)[Si](C)(C)C)C=C14109.9Semi standard non polar33892256
Di-4-coumaroylputrescine,2TMS,isomer #4C[Si](C)(C)N(CCCCN(C(=O)/C=C/C1=CC=C(O)C=C1)[Si](C)(C)C)C(=O)/C=C/C1=CC=C(O)C=C14124.0Semi standard non polar33892256
Di-4-coumaroylputrescine,3TMS,isomer #1C[Si](C)(C)OC1=CC=C(/C=C/C(=O)NCCCCN(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C=C2)[Si](C)(C)C)C=C14127.2Semi standard non polar33892256
Di-4-coumaroylputrescine,3TMS,isomer #1C[Si](C)(C)OC1=CC=C(/C=C/C(=O)NCCCCN(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C=C2)[Si](C)(C)C)C=C13974.5Standard non polar33892256
Di-4-coumaroylputrescine,3TMS,isomer #2C[Si](C)(C)OC1=CC=C(/C=C/C(=O)N(CCCCN(C(=O)/C=C/C2=CC=C(O)C=C2)[Si](C)(C)C)[Si](C)(C)C)C=C14089.2Semi standard non polar33892256
Di-4-coumaroylputrescine,3TMS,isomer #2C[Si](C)(C)OC1=CC=C(/C=C/C(=O)N(CCCCN(C(=O)/C=C/C2=CC=C(O)C=C2)[Si](C)(C)C)[Si](C)(C)C)C=C13847.1Standard non polar33892256
Di-4-coumaroylputrescine,4TMS,isomer #1C[Si](C)(C)OC1=CC=C(/C=C/C(=O)N(CCCCN(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C=C2)[Si](C)(C)C)[Si](C)(C)C)C=C14092.5Semi standard non polar33892256
Di-4-coumaroylputrescine,4TMS,isomer #1C[Si](C)(C)OC1=CC=C(/C=C/C(=O)N(CCCCN(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C=C2)[Si](C)(C)C)[Si](C)(C)C)C=C13670.3Standard non polar33892256
Di-4-coumaroylputrescine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)NCCCCNC(=O)/C=C/C2=CC=C(O)C=C2)C=C14338.8Semi standard non polar33892256
Di-4-coumaroylputrescine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(CCCCNC(=O)/C=C/C1=CC=C(O)C=C1)C(=O)/C=C/C1=CC=C(O)C=C14315.3Semi standard non polar33892256
Di-4-coumaroylputrescine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)NCCCCNC(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C=C14740.2Semi standard non polar33892256
Di-4-coumaroylputrescine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)N(CCCCNC(=O)/C=C/C2=CC=C(O)C=C2)[Si](C)(C)C(C)(C)C)C=C14642.9Semi standard non polar33892256
Di-4-coumaroylputrescine,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)NCCCCN(C(=O)/C=C/C2=CC=C(O)C=C2)[Si](C)(C)C(C)(C)C)C=C14643.6Semi standard non polar33892256
Di-4-coumaroylputrescine,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)N(CCCCN(C(=O)/C=C/C1=CC=C(O)C=C1)[Si](C)(C)C(C)(C)C)C(=O)/C=C/C1=CC=C(O)C=C14587.7Semi standard non polar33892256
Di-4-coumaroylputrescine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)NCCCCN(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)[Si](C)(C)C(C)(C)C)C=C14907.6Semi standard non polar33892256
Di-4-coumaroylputrescine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)NCCCCN(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)[Si](C)(C)C(C)(C)C)C=C14517.4Standard non polar33892256
Di-4-coumaroylputrescine,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)N(CCCCN(C(=O)/C=C/C2=CC=C(O)C=C2)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C14816.1Semi standard non polar33892256
Di-4-coumaroylputrescine,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)N(CCCCN(C(=O)/C=C/C2=CC=C(O)C=C2)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C14296.2Standard non polar33892256
Di-4-coumaroylputrescine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)N(CCCCN(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C15031.3Semi standard non polar33892256
Di-4-coumaroylputrescine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)N(CCCCN(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C14215.5Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Di-4-coumaroylputrescine GC-MS (Non-derivatized) - 70eV, Positivesplash10-016s-1920000000-497bd0d6572bc632dd6a2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Di-4-coumaroylputrescine GC-MS (2 TMS) - 70eV, Positivesplash10-014i-1190010000-4f10b7baca60f8c2c7f92017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Di-4-coumaroylputrescine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Di-4-coumaroylputrescine 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 - Di-4-coumaroylputrescine 10V, Positive-QTOFsplash10-001i-2295000000-98102610eb06433b23112016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Di-4-coumaroylputrescine 20V, Positive-QTOFsplash10-00kr-9460000000-c25644a3f7325cfa3c9d2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Di-4-coumaroylputrescine 40V, Positive-QTOFsplash10-00ri-9500000000-f8efed01bbbfa0f2a3e62016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Di-4-coumaroylputrescine 10V, Negative-QTOFsplash10-004i-0219000000-81920b181975731403972016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Di-4-coumaroylputrescine 20V, Negative-QTOFsplash10-03fr-0956000000-4fdcb8cb5ca0d6c705b42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Di-4-coumaroylputrescine 40V, Negative-QTOFsplash10-01ox-6900000000-df2223def2a642b944ba2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Di-4-coumaroylputrescine 10V, Positive-QTOFsplash10-001i-0009000000-b4027030ec67e9594d182021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Di-4-coumaroylputrescine 20V, Positive-QTOFsplash10-001j-0946000000-bd6bf86b5f6810299c122021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Di-4-coumaroylputrescine 40V, Positive-QTOFsplash10-0gb9-2901000000-f6529f1ad27d5e4860c22021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Di-4-coumaroylputrescine 10V, Negative-QTOFsplash10-004i-0009000000-210e3a4405f0f36aaf5d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Di-4-coumaroylputrescine 20V, Negative-QTOFsplash10-00or-0749000000-92b4d555d08e97cee48b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Di-4-coumaroylputrescine 40V, Negative-QTOFsplash10-014i-0910000000-dc4a742c33368c2345222021-09-24Wishart 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 IDFDB011508
KNApSAcK IDC00054926
Chemspider ID30777007
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound44241258
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1835861
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.. .