Record Information
Version1.0
Creation date2010-04-08 22:05:20 UTC
Update date2020-02-24 19:10:29 UTC
Primary IDFDB002330
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameHordatine A
DescriptionHordatine A belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. Hordatine A is a very strong basic compound (based on its pKa). Hordatine A has been detected, but not quantified in, barley and cereals and cereal products. This could make hordatine a a potential biomarker for the consumption of these foods.
CAS Number7073-64-5
Structure
Thumb
Synonyms
SynonymSource
N-(4-Carbamimidamidobutyl)-5-[(1Z)-2-[(4-carbamimidamidobutyl)-C-hydroxycarbonimidoyl]eth-1-en-1-yl]-7-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-3-carboximidateGenerator
Hordatine Adb_source
Predicted Properties
PropertyValueSource
Water Solubility0.066 g/LALOGPS
logP1.05ALOGPS
logP-0.42ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)9.25ChemAxon
pKa (Strongest Basic)12.43ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area231.69 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity176.95 m³·mol⁻¹ChemAxon
Polarizability59.72 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC28H38N8O5
IUPAC nameN-(4-carbamimidamidobutyl)-5-[(1Z)-2-[(4-carbamimidamidobutyl)carbamoyl]eth-1-en-1-yl]-7-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-3-carboxamide
InChI IdentifierInChI=1S/C28H38N8O5/c29-27(30)35-13-3-1-11-33-22(39)10-5-17-15-20-23(26(40)34-12-2-4-14-36-28(31)32)24(41-25(20)21(38)16-17)18-6-8-19(37)9-7-18/h5-10,15-16,23-24,37-38H,1-4,11-14H2,(H,33,39)(H,34,40)(H4,29,30,35)(H4,31,32,36)/b10-5-
InChI KeyFCINNGNGQHGDFW-YHYXMXQVSA-N
Isomeric SMILESNC(=N)NCCCCNC(=O)\C=C/C1=CC(O)=C2OC(C(C(=O)NCCCCNC(N)=N)C2=C1)C1=CC=C(O)C=C1
Average Molecular Weight566.6519
Monoisotopic Molecular Weight566.296516366
Classification
Description Belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
Class2-arylbenzofuran flavonoids
Sub ClassNot Available
Direct Parent2-arylbenzofuran flavonoids
Alternative Parents
Substituents
  • 2-arylbenzofuran flavonoid
  • Neolignan skeleton
  • Benzofuran
  • Coumaran
  • Styrene
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboxamide group
  • Guanidine
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Ether
  • Oxacycle
  • Organoheterocyclic compound
  • Carboximidamide
  • Imine
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organic oxide
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organopnictogen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 59.35%; H 6.76%; N 19.77%; O 14.12%DFC
Melting PointMp 132-135° (as dipicrate)DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]23D +69 (c, 1 in H2O)DFC
Spectroscopic UV Data305 (e 18700) (MeOH-NaOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSHordatine A, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-052r-2000910000-2e304712159bb96b1f02Spectrum
Predicted GC-MSHordatine A, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-074r-2100091000-7356eb58e753039dac02Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-1900250000-dec849606be2049a4813Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01t9-5900110000-a55082492e274b26c4e8Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01t9-6911000000-f0903d6f1154d6562458Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00xr-2000490000-ef4ff5c34ecb87c303a9Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-7102960000-947b9d4ba0b2dd52b9cfSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9121100000-a9d0de5807fec2193bb5Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC08307
Pubchem Compound ID5281113
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB30461
CRC / DFC (Dictionary of Food Compounds) IDCKG39-H:CKG42-D
EAFUS IDNot Available
Dr. Duke IDHORDATINE-A
BIGG IDNot Available
KNApSAcK IDC00001415
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
allelopathicDUKE
fungicide24127 A substance used to destroy fungal pests.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.