Cannabis Compound Database: Showing Compound Card for Cannabisin A (CDB000766)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (3) Show 6 proteins XML

Record Information

Version

1.0

Created at

2020-03-19 00:55:46 UTC

Updated at

2020-12-07 19:07:45 UTC

CannabisDB ID

CDB000766

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Cannabisin A

Description

Cannabisin A 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‚àö√á¬¨¬• 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 A was first isolated from the fruits of cannabis plants ( Ref:DOI ). It is a neutral, hydrophobic molecule that is largely insoluble in water. 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 Œ± (TNF-Œ±) in a concentration-dependent manner in LPS-stimulated BV2 microglia cells (PMID: 30691004 ).

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Not Available

Chemical Formula

C₃₄H₃₀N₂O₈

Average Molecular Weight

594.62

Monoisotopic Molecular Weight

594.2002

IUPAC Name

1-(3,4-dihydroxyphenyl)-6,7-dihydroxy-N2,N3-bis[2-(4-hydroxyphenyl)ethyl]naphthalene-2,3-dicarboxamide

Traditional Name

1-(3,4-dihydroxyphenyl)-6,7-dihydroxy-N2,N3-bis[2-(4-hydroxyphenyl)ethyl]naphthalene-2,3-dicarboxamide

CAS Registry Number

Not Available

SMILES

OC(=NCCC1=CC=C(O)C=C1)C1=C(C(O)=NCCC2=CC=C(O)C=C2)C(C2=CC(O)=C(O)C=C2)=C2C=C(O)C(O)=CC2=C1

InChI Identifier

InChI=1S/C34H30N2O8/c37-23-6-1-19(2-7-23)11-13-35-33(43)26-15-22-17-29(41)30(42)18-25(22)31(21-5-10-27(39)28(40)16-21)32(26)34(44)36-14-12-20-3-8-24(38)9-4-20/h1-10,15-18,37-42H,11-14H2,(H,35,43)(H,36,44)

InChI Key

CLNINZAIEQRASP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as arylnaphthalene lignans. These are lignans containing the arylnaphthalene skeleton, especially 9-(2H-1,3-benzodioxol-5-yl)-1H,3H-naphtho[2,3-c]furan-1-one or a derivative thereof. Arylnaphthalene lignans occur in nature and exhibit diverse biological activities.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Arylnaphthalene lignans

Sub Class

Not Available

Direct Parent

Arylnaphthalene lignans

Alternative Parents

Substituents

Arylnaphthalene lignan skeleton
2-naphthalenecarboxamide
2-naphthalenecarboxylic acid or derivatives
2-naphthol
Naphthalene
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid derivative
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Role

Industrial application:

Household products:

Pesticide:

Insect repellent

Pharmaceutical industry:

Biological role:

Antioxidant

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
logP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.71	ALOGPS
logP	4.96	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	8.61	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	179.58 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	166.22 m³·mol⁻¹	ChemAxon
Polarizability	63.09 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Cannabisin A, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Cannabisin A, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Cannabisin A, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Cannabisin A, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Cannabisin A, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Cannabisin A, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Cannabisin A, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Cannabisin A, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2020-06-30	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2020-06-30	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2020-06-30	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2020-06-30	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2020-06-30	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2020-06-30	View Spectrum

NMR

Not Available

Pathways

Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Acetylcholinesterase	ACHE	7q22	P22303	details
Tumor necrosis factor	TNF	6p21.3	P01375	details
Interleukin-6	IL6	7p21	P05231	details

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Protein Name	Gene Name	Locus	Uniprot ID	Details
Acetylcholinesterase	ACHE	7q22	P22303	details
Tumor necrosis factor	TNF	6p21.3	P01375	details
Interleukin-6	IL6	7p21	P05231	details

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00000667

Chemspider ID

Not Available

KEGG Compound ID

C17905

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15086398

PDB ID

Not Available

ChEBI ID

Not Available

References

General References

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 ]
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

Showing Compound Card for Cannabisin A (CDB000766)

Structure for CDB000766 (Cannabisin A)

Enzymes