Showing Compound Card for Cannabisin C (CDB000769)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (3) Show 6 proteinsXML
Record Information
Version1.0
Created at2020-03-19 00:56:00 UTC
Updated at2020-12-07 19:07:45 UTC
CannabisDB IDCDB000769
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameCannabisin C
DescriptionCannabisin C, is a methylated derivative of cannabisin B. It is a lignanamide that 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. Cannabisin C has been isolated from the roots, fruits and seeds of cannabis plants (PMID: 28799497 ). It is a neutral, hydrophobic molecule that is largely insoluble in water. Even though relatively little information exists regarding the biological function of cannabisin C, it has been established that its analog cannabisin B functions predominantly as an antioxidant (PMID: 23411211 ). It has also been established that cannabisin B has considerable antiproliferative potential by inducing the autphagic cell death of HepG2 cells. This suggests it may be a promising agent to treat hepatoblastoma disease (PMID: 23411211 ). 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, antioxidant 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
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
SynonymsNot Available
Chemical FormulaC35H34N2O8
Average Molecular Weight610.66
Monoisotopic Molecular Weight610.2315
IUPAC Name(1R,2S)-1-(3,4-dihydroxyphenyl)-7-hydroxy-N-[2-(4-hydroxyphenyl)ethyl]-3-{[2-(4-hydroxyphenyl)ethyl]carbamoyl}-6-methoxy-1,2-dihydronaphthalene-2-carboximidic acid
Traditional Name(1R,2S)-1-(3,4-dihydroxyphenyl)-7-hydroxy-N-[2-(4-hydroxyphenyl)ethyl]-3-{[2-(4-hydroxyphenyl)ethyl]carbamoyl}-6-methoxy-1,2-dihydronaphthalene-2-carboximidic acid
CAS Registry NumberNot Available
SMILES
COC1=C(O)C=C2[C@H]([C@H](C(O)=NCCC3=CC=C(O)C=C3)C(=CC2=C1)C(=O)NCCC1=CC=C(O)C=C1)C1=CC(O)=C(O)C=C1
InChI Identifier
InChI=1S/C35H34N2O8/c1-45-31-18-23-16-27(34(43)36-14-12-20-2-7-24(38)8-3-20)33(35(44)37-15-13-21-4-9-25(39)10-5-21)32(26(23)19-30(31)42)22-6-11-28(40)29(41)17-22/h2-11,16-19,32-33,38-42H,12-15H2,1H3,(H,36,43)(H,37,44)/t32-,33-/m1/s1
InChI KeyKTJXNTJMKBMZKA-CZNDPXEESA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aryltetralin lignans. These are lignans with a structure based on the 1-phenyltetralin skeleton.
KingdomOrganic compounds
Super ClassLignans, neolignans and related compounds
ClassAryltetralin lignans
Sub ClassNot Available
Direct ParentAryltetralin lignans
Alternative Parents
Substituents
  • 1-aryltetralin lignan
  • 2-naphthalenecarboxylic acid or derivatives
  • Naphthalene
  • Anisole
  • Phenol ether
  • Catechol
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Ether
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic 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
logP4.2ALOGPS
logP4.18ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)3.06ChemAxon
pKa (Strongest Basic)5.56ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area172.07 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity170.6 m³·mol⁻¹ChemAxon
Polarizability65.24 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-MSCannabisin C, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCannabisin C, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCannabisin C, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCannabisin C, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCannabisin C, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCannabisin C, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCannabisin C, 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
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 Compound101631693
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. Chen T, Hao J, He J, Zhang J, Li Y, Liu R, Li L: Cannabisin B induces autophagic cell death by inhibiting the AKT/mTOR pathway and S phase cell cycle arrest in HepG2 cells. Food Chem. 2013 Jun 1;138(2-3):1034-41. doi: 10.1016/j.foodchem.2012.11.102. Epub 2012 Dec 5. [PubMed:23411211 ]
  3. 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 ]
  4. 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