Showing Compound Card for 3,3'-Demethyl-grossamide (CDB000776)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (2) Show 4 proteinsXML
Record Information
Version1.0
Created at2020-03-19 00:56:25 UTC
Updated at2020-12-07 19:07:45 UTC
CannabisDB IDCDB000776
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name3,3'-Demethyl-grossamide
Description3,3'-demethyl-grossamide is a demethylated derivative of grossamide. 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-grossamide is one of several lignanamides that have been identified in hemp seed (cannabis) (PMID: 26585089 ). The methylated version of 3,3'-demethyl-grossamide (Grossamide) has been shown to exhibit anti-inÔ¨Çammatory and anti-neuroinflammatory activity via the suppression of TLR-4 mediated NF-kappaB signalling pathways (PMID: 28224333 ). It has been found to significantly inhibit the secretion of pro-inflammatory mediators such as interleukin 6 (IL-6) and tumor necrosis factor α (TNF-α) in cell culture (PMID: 28224333 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2R,3S)-2-(3,4-Dihydroxyphenyl)-7-hydroxy-N-[2-(4-hydroxyphenyl)ethyl]-5-(2-{[2-(4-hydroxyphenyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)-2,3-dihydro-1-benzofuran-3-carboximidateGenerator
Chemical FormulaC34H34N2O8
Average Molecular Weight598.65
Monoisotopic Molecular Weight598.2315
IUPAC Name(2R,3S)-2-(3,4-dihydroxyphenyl)-7-hydroxy-N-[2-(4-hydroxyphenyl)ethyl]-5-(2-{[2-(4-hydroxyphenyl)ethyl]carbamoyl}ethyl)-2,3-dihydro-1-benzofuran-3-carboxamide
Traditional Name(2R,3S)-2-(3,4-dihydroxyphenyl)-7-hydroxy-N-[2-(4-hydroxyphenyl)ethyl]-5-(2-{[2-(4-hydroxyphenyl)ethyl]carbamoyl}ethyl)-2,3-dihydro-1-benzofuran-3-carboxamide
CAS Registry NumberNot Available
SMILES
OC1=CC=C(CCNC(=O)CCC2=CC(O)=C3O[C@H]([C@@H](C(=O)NCCC4=CC=C(O)C=C4)C3=C2)C2=CC(O)=C(O)C=C2)C=C1
InChI Identifier
InChI=1S/C34H34N2O8/c37-24-7-1-20(2-8-24)13-15-35-30(42)12-5-22-17-26-31(34(43)36-16-14-21-3-9-25(38)10-4-21)32(44-33(26)29(41)18-22)23-6-11-27(39)28(40)19-23/h1-4,6-11,17-19,31-32,37-41H,5,12-16H2,(H,35,42)(H,36,43)/t31-,32-/m0/s1
InChI KeyVYSIAZZYOTZLFI-ACHIHNKUSA-N
Chemical Taxonomy
ClassificationNot classified
Ontology
Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.59ALOGPS
logP4.44ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)8.85ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area168.58 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity164.19 m³·mol⁻¹ChemAxon
Polarizability64.38 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-grossamide, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3,3'-Demethyl-grossamide, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3,3'-Demethyl-grossamide, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3,3'-Demethyl-grossamide, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3,3'-Demethyl-grossamide, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3,3'-Demethyl-grossamide, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3,3'-Demethyl-grossamide, 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
Tumor necrosis factorTNF6p21.3P01375 details
Interleukin-6IL67p21P05231 details
TransportersNot Available
Metal BindingsNot Available
Receptors
Protein NameGene NameLocusUniprot IDDetails
Tumor necrosis factorTNF6p21.3P01375 details
Interleukin-6IL67p21P05231 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 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. Luo Q, Yan X, Bobrovskaya L, Ji M, Yuan H, Lou H, Fan P: Anti-neuroinflammatory effects of grossamide from hemp seed via suppression of TLR-4-mediated NF-kappaB signaling pathways in lipopolysaccharide-stimulated BV2 microglia cells. Mol Cell Biochem. 2017 Apr;428(1-2):129-137. doi: 10.1007/s11010-016-2923-7. Epub 2017 Feb 21. [PubMed:28224333 ]

Enzymes

Enzyme Details
1. Tumor necrosis factor
General function:
Involved in tumor necrosis factor receptor binding
Specific function:
Cytokine that binds to TNFRSF1A/TNFR1 and TNFRSF1B/TNFBR. It is mainly secreted by macrophages and can induce cell death of certain tumor cell lines. It is potent pyrogen causing fever by direct action or by stimulation of interleukin-1 secretion and is implicated in the induction of cachexia, Under certain conditions it can stimulate cell proliferation and induce cell differentiation
Gene Name:
TNF
Uniprot ID:
P01375
Molecular weight:
25644.1
Enzyme Details
2. Interleukin-6
General function:
Involved in cytokine activity
Specific function:
Cytokine with a wide variety of biological functions. It is a potent inducer of the acute phase response. Plays an essential role in the final differentiation of B-cells into Ig- secreting cells Involved in lymphocyte and monocyte differentiation. It induces myeloma and plasmacytoma growth and induces nerve cells differentiation Acts on B-cells, T-cells, hepatocytes, hematopoeitic progenitor cells and cells of the CNS. Also acts as a myokine. It is discharged into the bloodstream after muscle contraction and acts to increase the breakdown of fats and to improve insulin resistance
Gene Name:
IL6
Uniprot ID:
P05231
Molecular weight:
23718.0