You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:11:37 UTC
Update Date2019-07-23 06:13:29 UTC
HMDB IDHMDB0033460
Secondary Accession Numbers
  • HMDB33460
Metabolite Identification
Common Name4-Hydroxycinnamoylagmatine
Description4-Hydroxycinnamoylagmatine, also known as trans-coumaroylagmatine, 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. 4-Hydroxycinnamoylagmatine is a very strong basic compound (based on its pKa). Outside of the human body, 4-Hydroxycinnamoylagmatine has been detected, but not quantified in, cereals and cereal products. This could make 4-hydroxycinnamoylagmatine a potential biomarker for the consumption of these foods. A p-coumaroylagmatine(1+) in which the double bond of the coumaroyl component has E-geochemistry.
Structure
Data?1563862409
Synonyms
ValueSource
(e)-CoumaroylagmatineChEBI
(e)-N-(4-Guanidinobutyl)-4-hydroxycinnamamideChEBI
1-(trans-4'-Hydroxycinnamoylamino)-4-guanidinobutaneChEBI
trans-CoumaroylagmatineChEBI
trans-p-CoumaroylagmatineChEBI
N-(4-Guanidinobutyl)-4-hydroxycinnamideKegg
N-(4-Guanidinobutyl)-4-hydroxycinnamamideKegg
cis-p-CoumaroylagmatineHMDB
N1-trans-p-CoumaroylagmatineHMDB
Chemical FormulaC14H20N4O2
Average Molecular Weight276.3342
Monoisotopic Molecular Weight276.158625904
IUPAC Name(2E)-N-(4-carbamimidamidobutyl)-3-(4-hydroxyphenyl)prop-2-enamide
Traditional Name(2E)-N-(4-carbamimidamidobutyl)-3-(4-hydroxyphenyl)prop-2-enamide
CAS Registry Number7295-86-5
SMILES
NC(=N)NCCCCNC(=O)\C=C\C1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C14H20N4O2/c15-14(16)18-10-2-1-9-17-13(20)8-5-11-3-6-12(19)7-4-11/h3-8,19H,1-2,9-10H2,(H,17,20)(H4,15,16,18)/b8-5+
InChI KeyAKIHYQWCLCDMMI-VMPITWQZSA-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
  • Guanidine
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Carboximidamide
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point215 - 217 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.21 g/LALOGPS
logP0.93ALOGPS
logP0.31ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)9.42ChemAxon
pKa (Strongest Basic)12.22ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area111.23 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity89.93 m³·mol⁻¹ChemAxon
Polarizability30.94 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-5900000000-dae641a9d8c5b411bb43Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-022d-8692000000-f43d311d6603321aa819Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-1940000000-073108419d02e5ccd9efSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03fr-5900000000-c7ebd6eb8c81870020b6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-9200000000-b958fc502e80b5e61211Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0059-1290000000-e3ee5ea565154da32314Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a59-7690000000-fe62d436c3fdfc1a6c0bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9200000000-584c6befeed25249f330Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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
FoodDB IDFDB011502
KNApSAcK IDC00028060
Chemspider ID4444279
KEGG Compound IDC04498
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5280691
PDB IDNot Available
ChEBI ID86080
Food Biomarker OntologyNot Available
VMH 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.. .