Showing Compound Card for (2,3-trans)-3-(3-hydroxy-5-methoxyphenyl)-N-(4- hydroxyphenethyl)-7-{(E)-3-[(4-hydroxyphenethyl) amino]-3-oxoprop-1-enyl}-2,3-dihydro-benzo [b] [1,4] dioxine-2-carboxamide (CDB000777)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (1) Show 2 proteinsXML
Record Information
Version1.0
Created at2020-03-19 00:56:29 UTC
Updated at2020-12-07 19:07:45 UTC
CannabisDB IDCDB000777
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name(2,3-trans)-3-(3-hydroxy-5-methoxyphenyl)-N-(4- hydroxyphenethyl)-7-{(E)-3-[(4-hydroxyphenethyl) amino]-3-oxoprop-1-enyl}-2,3-dihydro-benzo [b] [1,4] dioxine-2-carboxamide
Description(2,3-trans)-3-(3-hydroxy-5-methoxyphenyl)-N-(4- hydroxyphenethyl)-7-{(E)-3-[(4-hydroxyphenethyl) amino]-3-oxoprop-1-enyl}-2,3-dihydro-benzo [b] [1,4] dioxine-2-carboxamide is an organic compound that is classified as lignanamide. It belongs to the class of organic compounds known as lignans, neolignans and related compounds. These are plant products of low molecular weight formed primarily from oxidative coupling of two p-propylphenol moieties. They can be attached in various manners, like C5-C5, C8-C8. Most known natural lignans are oxidized at C9 and C9´ and, based upon the way in which oxygen is incorporated into the skeleton and on the cyclization patterns, a wide range of lignans of very different structural types can be formed. This particular lignanamide was first identified in 2015 in hemp seeds (PMID: 26585089 ) and is currently an un-named cannabasin. Lignanamides exhibit interesting and diverse biological activities, including feeding deterrent activity and insecticidal effects (that protect the plant) as well as anti-inflammatory, anti-oxidant and anti-acetylcholinesterase activity, which may have beneficial health effects (PMID: 26585089 )
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
SynonymsNot Available
Chemical FormulaC35H34N2O8
Average Molecular Weight610.66
Monoisotopic Molecular Weight610.2315
IUPAC Name(2S,3R)-3-(3-hydroxy-5-methoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]-7-[(1E)-2-{[2-(4-hydroxyphenyl)ethyl]carbamoyl}eth-1-en-1-yl]-2,3-dihydro-1,4-benzodioxine-2-carboxamide
Traditional Name(2S,3R)-3-(3-hydroxy-5-methoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]-7-[(1E)-2-{[2-(4-hydroxyphenyl)ethyl]carbamoyl}eth-1-en-1-yl]-2,3-dihydro-1,4-benzodioxine-2-carboxamide
CAS Registry NumberNot Available
SMILES
COC1=CC(=CC(O)=C1)[C@H]1OC2=C(O[C@@H]1C(=O)NCCC1=CC=C(O)C=C1)C=C(\C=C\C(=O)NCCC1=CC=C(O)C=C1)C=C2
InChI Identifier
InChI=1S/C35H34N2O8/c1-43-29-20-25(19-28(40)21-29)33-34(35(42)37-17-15-23-4-10-27(39)11-5-23)45-31-18-24(6-12-30(31)44-33)7-13-32(41)36-16-14-22-2-8-26(38)9-3-22/h2-13,18-21,33-34,38-40H,14-17H2,1H3,(H,36,41)(H,37,42)/b13-7+/t33-,34+/m1/s1
InChI KeyABUYVRIWKJMSGL-RULIJYEHSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylbenzo-1,4-dioxanes. These are benzo-1,3-dioxanes having a phenyl group attached to the 1,4-dioxane moiety.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzodioxanes
Sub ClassPhenylbenzodioxanes
Direct ParentPhenylbenzo-1,4-dioxanes
Alternative Parents
Substituents
  • 2-phenylbenzo-1,4-dioxane
  • Cinnamic acid or derivatives
  • Cinnamic acid amide
  • Methoxyphenol
  • Benzo-1,4-dioxane
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Styrene
  • Phenol ether
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Para-dioxin
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Oxacycle
  • Carboxylic acid derivative
  • Ether
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP4.22ALOGPS
logP4.91ChemAxon
logS-5.7ALOGPS
pKa (Strongest Acidic)8.95ChemAxon
pKa (Strongest Basic)-0.39ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area146.58 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity168.71 m³·mol⁻¹ChemAxon
Polarizability66.09 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS(2,3-trans)-3-(3-hydroxy-5-methoxyphenyl)-N-(4- hydroxyphenethyl)-7-{(E)-3-[(4-hydroxyphenethyl) amino]-3-oxoprop-1-enyl}-2,3-dihydro-benzo [b] [1,4] dioxine-2-carboxamide, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(2,3-trans)-3-(3-hydroxy-5-methoxyphenyl)-N-(4- hydroxyphenethyl)-7-{(E)-3-[(4-hydroxyphenethyl) amino]-3-oxoprop-1-enyl}-2,3-dihydro-benzo [b] [1,4] dioxine-2-carboxamide, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(2,3-trans)-3-(3-hydroxy-5-methoxyphenyl)-N-(4- hydroxyphenethyl)-7-{(E)-3-[(4-hydroxyphenethyl) amino]-3-oxoprop-1-enyl}-2,3-dihydro-benzo [b] [1,4] dioxine-2-carboxamide, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(2,3-trans)-3-(3-hydroxy-5-methoxyphenyl)-N-(4- hydroxyphenethyl)-7-{(E)-3-[(4-hydroxyphenethyl) amino]-3-oxoprop-1-enyl}-2,3-dihydro-benzo [b] [1,4] dioxine-2-carboxamide, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(2,3-trans)-3-(3-hydroxy-5-methoxyphenyl)-N-(4- hydroxyphenethyl)-7-{(E)-3-[(4-hydroxyphenethyl) amino]-3-oxoprop-1-enyl}-2,3-dihydro-benzo [b] [1,4] dioxine-2-carboxamide, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available2020-06-30View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
AcetylcholinesteraseACHE7q22P22303 details
TransportersNot Available
Metal BindingsNot Available
Receptors
Protein NameGene NameLocusUniprot IDDetails
AcetylcholinesteraseACHE7q22P22303 details
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound71521886
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Yan X, Tang J, dos Santos Passos C, Nurisso A, Simoes-Pires CA, Ji M, Lou H, Fan P: Characterization of Lignanamides from Hemp (Cannabis sativa L.) Seed and Their Antioxidant and Acetylcholinesterase Inhibitory Activities. J Agric Food Chem. 2015 Dec 16;63(49):10611-9. doi: 10.1021/acs.jafc.5b05282. Epub 2015 Dec 2. [PubMed:26585089 ]

Enzymes

Enzyme Details
1. Acetylcholinesterase
General function:
Involved in carboxylesterase activity
Specific function:
Terminates signal transduction at the neuromuscular junction by rapid hydrolysis of the acetylcholine released into the synaptic cleft. Role in neuronal apoptosis.
Gene Name:
ACHE
Uniprot ID:
P22303
Molecular weight:
67795.525