Showing Compound Card for 3,3'-Demethyl-heliotropamide (CDB000778)

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Record Information
Version1.0
Created at2020-03-19 00:56:33 UTC
Updated at2020-11-18 16:35:30 UTC
CannabisDB IDCDB000778
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name3,3'-Demethyl-heliotropamide
Description3,3'-demethyl-heliotropamide is a demethylated derivative of heliotropamide. It is a lignanamide and 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. 3,3'-demethyl-heliotropamide has been identified from hemp (cannabis) seed. It exists as a colorless amorphous powder (PMID: 26585089 ). Heliotropamides were first isolated in 2003 from the plant Heliotropium ovalifolium (PMID: 14695794 ), from which they derive their name.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2S,3R,4E)-2-(3,4-Dihydroxyphenyl)-4-[(3,4-dihydroxyphenyl)methylidene]-N-[2-(4-hydroxyphenyl)ethyl]-1-[2-(4-methylphenyl)ethyl]-5-oxopyrrolidine-3-carboximidateGenerator
Chemical FormulaC35H34N2O7
Average Molecular Weight594.66
Monoisotopic Molecular Weight594.2366
IUPAC Name(3R,4E)-2-(3,4-dihydroxyphenyl)-4-[(3,4-dihydroxyphenyl)methylidene]-N-[2-(4-hydroxyphenyl)ethyl]-1-[2-(4-methylphenyl)ethyl]-5-oxopyrrolidine-3-carboxamide
Traditional Name(3R,4E)-2-(3,4-dihydroxyphenyl)-4-[(3,4-dihydroxyphenyl)methylidene]-N-[2-(4-hydroxyphenyl)ethyl]-1-[2-(4-methylphenyl)ethyl]-5-oxopyrrolidine-3-carboxamide
CAS Registry NumberNot Available
SMILES
CC1=CC=C(CCN2C([C@H](C(=O)NCCC3=CC=C(O)C=C3)\C(=C/C3=CC=C(O)C(O)=C3)C2=O)C2=CC=C(O)C(O)=C2)C=C1
InChI Identifier
InChI=1S/C35H34N2O7/c1-21-2-4-23(5-3-21)15-17-37-33(25-9-13-29(40)31(42)20-25)32(34(43)36-16-14-22-6-10-26(38)11-7-22)27(35(37)44)18-24-8-12-28(39)30(41)19-24/h2-13,18-20,32-33,38-42H,14-17H2,1H3,(H,36,43)/b27-18+/t32-,33-/m1/s1
InChI KeyIAVLSVVJBRDTTD-JTYZNVFISA-N
Chemical Taxonomy
ClassificationNot classified
Ontology
Not Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP4.23ALOGPS
logP5.3ChemAxon
logS-5.6ALOGPS
pKa (Strongest Acidic)8.82ChemAxon
pKa (Strongest Basic)-0.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area150.56 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity168.07 m³·mol⁻¹ChemAxon
Polarizability63.32 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-MS3,3'-Demethyl-heliotropamide, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3,3'-Demethyl-heliotropamide, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3,3'-Demethyl-heliotropamide, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3,3'-Demethyl-heliotropamide, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3,3'-Demethyl-heliotropamide, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3,3'-Demethyl-heliotropamide, 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
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
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 CompoundNot Available
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 ]
  2. Guntern A, Ioset JR, Queiroz EF, Sandor P, Foggin CM, Hostettmann K: Heliotropamide, a novel oxopyrrolidine-3-carboxamide from Heliotropium ovalifolium. J Nat Prod. 2003 Dec;66(12):1550-3. doi: 10.1021/np0302495. [PubMed:14695794 ]