Showing Compound Card for Grossamide (CDB000775)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (2) Show 4 proteinsXML
Record Information
Version1.0
Created at2020-03-19 00:56:22 UTC
Updated at2020-12-07 19:07:45 UTC
CannabisDB IDCDB000775
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameGrossamide
DescriptionGrossamide, also known as (+-)-grossamide or tribulusamide A, is a lignanamide. It belongs to the class of organic compounds known as lignans, neolignans and related compounds. Lignanamides 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√Ǭ¥ 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. Grossamide is a naturally occuring organic compound and one of several lignanamides found in cannabis plants and has been isolated from the herbal plant hemp seed (fructus cannabis, the dried fruit of Cannabis sativa) (PMID: 26585089 ). Grossamide is also found within a few different foods, such as yellow bell peppers, red bell peppers, and pepper (Capsicum annuum) and in a lower concentration in orange bell peppers and green bell peppers. Grossamide has also been detected, but not quantified in herbs and spices and italian sweet red peppers. This could make grossamide a potential biomarker for the consumption of these foods. Grossamide exhibits anti-inÔ¨Çammatory and anti-neuroinflammatory activity and suppresses 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
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
SynonymsNot Available
Chemical FormulaC36H36N2O8
Average Molecular Weight624.69
Monoisotopic Molecular Weight624.2472
IUPAC Name(2S,3S)-2-(4-hydroxy-3-methoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]-5-[(1E)-2-[(Z)-[2-(4-hydroxyphenyl)ethyl]-C-hydroxycarbonimidoyl]eth-1-en-1-yl]-7-methoxy-2,3-dihydro-1-benzofuran-3-carboximidic acid
Traditional Name(2S,3S)-2-(4-hydroxy-3-methoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]-5-[(1E)-2-[(Z)-[2-(4-hydroxyphenyl)ethyl]-C-hydroxycarbonimidoyl]eth-1-en-1-yl]-7-methoxy-2,3-dihydro-1-benzofuran-3-carboximidic acid
CAS Registry Number80510-06-1
SMILES
COC1=CC(\C=C\C(\O)=N\CCC2=CC=C(O)C=C2)=CC2=C1O[C@@H]([C@H]2C(O)=NCCC1=CC=C(O)C=C1)C1=CC(OC)=C(O)C=C1
InChI Identifier
InChI=1S/C36H36N2O8/c1-44-30-21-25(8-13-29(30)41)34-33(36(43)38-18-16-23-5-11-27(40)12-6-23)28-19-24(20-31(45-2)35(28)46-34)7-14-32(42)37-17-15-22-3-9-26(39)10-4-22/h3-14,19-21,33-34,39-41H,15-18H2,1-2H3,(H,37,42)(H,38,43)/b14-7+/t33-,34+/m0/s1
InChI KeyDROXVBRNXCRUHP-XALRPAEYSA-N
Chemical Taxonomy
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
  • Cinnamic acid amide
  • Cinnamic acid or derivatives
  • Methoxyphenol
  • Benzofuran
  • Coumaran
  • Anisole
  • Phenoxy compound
  • Phenol ether
  • Styrene
  • Methoxybenzene
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Benzenoid
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Ether
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organic oxide
  • Carbonyl group
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
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
logP5.18ALOGPS
logP4.56ChemAxon
logS-5.6ALOGPS
pKa (Strongest Acidic)2.62ChemAxon
pKa (Strongest Basic)6.27ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area153.56 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity175.29 m³·mol⁻¹ChemAxon
Polarizability68.78 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-MSGrossamide, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGrossamide, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGrossamide, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGrossamide, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGrossamide, 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 Compound101262727
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