Showing Compound Card for Cannabisin O (CDB000774)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (3) Show 6 proteinsXML
Record Information
Version1.0
Created at2020-03-19 00:56:19 UTC
Updated at2020-12-07 19:07:45 UTC
CannabisDB IDCDB000774
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameCannabisin O
DescriptionCannabisin O is a lignanamide. It belongs to the class of organic compounds known as lignans, neolignans and related compounds and is the first reported case of trimeric feruloyltyramine identified in cannabis seed extracts. 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. Cannabisin O has been isolated from the seeds of cannabis plants (PMID: 28799497 ). It is a neutral, hydrophobic molecule that is largely insoluble in water (PMID: 26585089 ). Cannabisins and other 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 ). Cannibasins have been found to suppress the production and lower the levels of mRNA of pro-inflammatory mediators such as interleukin 6 (IL-6) and tumor necrosis factor α (TNF-α) in a concentration-dependent manner in LPS-stimulated BV2 microglia cells (PMID: 30691004 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2S,3S)-5-[(1Z)-2-{4-[(1Z)-2-hydroxy-2-{[2-(4-hydroxyphenyl)ethyl]-C-hydroxycarbonimidoyl}eth-1-en-1-yl]-2-methoxyphenoxy}-2-{[2-(4-hydroxyphenyl)ethyl]-C-hydroxycarbonimidoyl}eth-1-en-1-yl]-2-(4-hydroxy-3-methoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]-7-methoxy-2,3-dihydro-1-benzofuran-3-carboximidateGenerator
Chemical FormulaC54H53N3O13
Average Molecular Weight952.03
Monoisotopic Molecular Weight951.3578
IUPAC Name(2S,3S)-5-[(1Z)-2-{4-[(1Z)-2-hydroxy-2-{[2-(4-hydroxyphenyl)ethyl]carbamoyl}eth-1-en-1-yl]-2-methoxyphenoxy}-2-{[2-(4-hydroxyphenyl)ethyl]carbamoyl}eth-1-en-1-yl]-2-(4-hydroxy-3-methoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]-7-methoxy-2,3-dihydro-1-benzofuran-3-carboxamide
Traditional Name(2S,3S)-5-[(1Z)-2-{4-[(1Z)-2-hydroxy-2-{[2-(4-hydroxyphenyl)ethyl]carbamoyl}eth-1-en-1-yl]-2-methoxyphenoxy}-2-{[2-(4-hydroxyphenyl)ethyl]carbamoyl}eth-1-en-1-yl]-2-(4-hydroxy-3-methoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]-7-methoxy-2,3-dihydro-1-benzofuran-3-carboxamide
CAS Registry NumberNot Available
SMILES
COC1=C2O[C@@H]([C@@H](C(=O)NCCC3=CC=C(O)C=C3)C2=CC(\C=C(/OC2=C(OC)C=C(\C=C(/O)C(=O)NCCC3=CC=C(O)C=C3)C=C2)C(=O)NCCC2=CC=C(O)C=C2)=C1)C1=CC=C(O)C(OC)=C1
InChI Identifier
InChI=1S/C54H53N3O13/c1-66-45-31-37(11-18-42(45)61)50-49(54(65)57-25-22-34-8-16-40(60)17-9-34)41-26-36(29-47(68-3)51(41)70-50)30-48(53(64)56-24-21-33-6-14-39(59)15-7-33)69-44-19-10-35(28-46(44)67-2)27-43(62)52(63)55-23-20-32-4-12-38(58)13-5-32/h4-19,26-31,49-50,58-62H,20-25H2,1-3H3,(H,55,63)(H,56,64)(H,57,65)/b43-27-,48-30-/t49-,50+/m0/s1
InChI KeyCSQQEMKVBJNOGU-RXPWIXMXSA-N
Chemical Taxonomy
ClassificationNot classified
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
logP5.83ALOGPS
logP6.71ChemAxon
logS-6.3ALOGPS
pKa (Strongest Acidic)8.06ChemAxon
pKa (Strongest Basic)-5.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area234.6 ŲChemAxon
Rotatable Bond Count20ChemAxon
Refractivity263.97 m³·mol⁻¹ChemAxon
Polarizability102 ųChemAxon
Number of Rings7ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
EI-MS/GC-MSNot Available
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
Tumor necrosis factorTNF6p21.3P01375 details
Interleukin-6IL67p21P05231 details
TransportersNot Available
Metal BindingsNot Available
Receptors
Protein NameGene NameLocusUniprot IDDetails
AcetylcholinesteraseACHE7q22P22303 details
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. Pollastro F, Minassi A, Fresu LG: Cannabis Phenolics and their Bioactivities. Curr Med Chem. 2018;25(10):1160-1185. doi: 10.2174/0929867324666170810164636. [PubMed:28799497 ]
  2. 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 ]
  3. Wang S, Luo Q, Fan P: Cannabisin F from Hemp (Cannabis sativa) Seed Suppresses Lipopolysaccharide-Induced Inflammatory Responses in BV2 Microglia as SIRT1 Modulator. Int J Mol Sci. 2019 Jan 25;20(3). pii: ijms20030507. doi: 10.3390/ijms20030507. [PubMed:30691004 ]

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
Enzyme Details
2. 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
3. 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