Cannabis Compound Database: Showing Compound Card for Isocannflavin B (CDB000745)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (3) Show 5 proteins XML

Record Information

Version

1.0

Created at

2020-03-19 00:54:30 UTC

Updated at

2020-12-07 19:07:44 UTC

CannabisDB ID

CDB000745

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Isocannflavin B

Description

Isocannflavin B, also known as 8-prenylapigenin if 8-PA, belongs to the class of organic compounds known as 8-prenylated flavones. These are flavones that feature a C5-isoprenoid substituent at the 8-position. Isocannflavin B is an isomer of cannflavin B where the position of the prenyl group is on C8, while in cannflavin B the prenyl group is attached to C6. Cannflavins are unique to Cannabis sativa (PMID: 3754224 ). Isocannflavin B exhibits ani-inflmmatory and vascular protective properties (PMID: 19686724 ). It is thought to be a COX-2 inhibitor and a non-selective strogen receptor antagonist (PMID: 19686724 ). Cannflavins were the first flavonoids identified to have direct inhibitory activity of two important pro-inflammatory mediators: arachidonate 5-lipoxygenase (5-LOX) and prostaglandin E synthase (mPGES-1).

Structure

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

Synonyms

Value	Source
Isocannflavin b	MeSH

Chemical Formula

C₂₁H₂₀O₆

Average Molecular Weight

368.39

Monoisotopic Molecular Weight

368.126

IUPAC Name

5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4H-chromen-4-one

Traditional Name

5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)chromen-4-one

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=CC(=C1)C1=CC(=O)C2=C(O)C=C(O)C(CC=C(C)C)=C2O1

InChI Identifier

InChI=1S/C21H20O6/c1-11(2)4-6-13-15(23)9-16(24)20-17(25)10-18(27-21(13)20)12-5-7-14(22)19(8-12)26-3/h4-5,7-10,22-24H,6H2,1-3H3

InChI Key

IHRNYHWGJUMPFJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 8-prenylated flavones. These are flavones that features a C5-isoprenoid substituent at the 8-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavones

Direct Parent

8-prenylated flavones

Alternative Parents

Substituents

8-prenylated flavone
3p-methoxyflavonoid-skeleton
Hydroxyflavonoid
7-hydroxyflavonoid
5-hydroxyflavonoid
4'-hydroxyflavonoid
Chromone
Benzopyran
1-benzopyran
Methoxyphenol
Methoxybenzene
Anisole
Phenoxy compound
Phenol ether
Alkyl aryl ether
Phenol
Pyranone
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Pyran
Vinylogous acid
Heteroaromatic compound
Organoheterocyclic compound
Oxacycle
Ether
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Role

Industrial application:

Pharmaceutical industry:

Anti-inflammatory

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	3.79	ALOGPS
logP	4.28	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	6.41	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	103.62 m³·mol⁻¹	ChemAxon
Polarizability	38.89 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Isocannflavin B, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Isocannflavin B, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Isocannflavin B, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Isocannflavin B, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Isocannflavin B, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Isocannflavin B, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Isocannflavin B, 3 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
Prostaglandin E synthase	PTGES	9q34.3	O14684	details
Arachidonate 5-lipoxygenase	ALOX5	10q11.2	P09917	details
Cytochrome c oxidase subunit 2	MT-CO2		P00403	details

Transporters

Not Available

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
Arachidonate 5-lipoxygenase	ALOX5	10q11.2	P09917	details
Cytochrome c oxidase subunit 2	MT-CO2		P00403	details

Receptors

Not Available

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

Not Available

Chemspider ID

23331865

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44562555

PDB ID

Not Available

ChEBI ID

Not Available

References

General References

Barrett ML, Scutt AM, Evans FJ: Cannflavin A and B, prenylated flavones from Cannabis sativa L. Experientia. 1986 Apr 15;42(4):452-3. doi: 10.1007/bf02118655. [PubMed:3754224 ]
Paoletti T, Fallarini S, Gugliesi F, Minassi A, Appendino G, Lombardi G: Anti-inflammatory and vascularprotective properties of 8-prenylapigenin. Eur J Pharmacol. 2009 Oct 12;620(1-3):120-30. doi: 10.1016/j.ejphar.2009.08.015. Epub 2009 Aug 15. [PubMed:19686724 ]

Enzymes

Enzyme Details

1. Prostaglandin E synthase

General function:: Involved in prostaglandin-E synthase activity
Specific function:: Catalyzes the oxidoreduction of prostaglandin endoperoxide H2 (PGH2) to prostaglandin E2 (PGE2).
Gene Name:: PTGES
Uniprot ID:: O14684
Molecular weight:: 17102.135

Enzyme Details

2. Arachidonate 5-lipoxygenase

General function:: Involved in metal ion binding
Specific function:: Catalyzes the first step in leukotriene biosynthesis, and thereby plays a role in inflammatory processes.
Gene Name:: ALOX5
Uniprot ID:: P09917
Molecular weight:: 77982.595

Enzyme Details

3. Cytochrome c oxidase subunit 2

General function:: Involved in copper ion binding
Specific function:: Cytochrome c oxidase is the component of the respiratory chain that catalyzes the reduction of oxygen to water. Subunits 1- 3 form the functional core of the enzyme complex. Subunit 2 transfers the electrons from cytochrome c via its binuclear copper A center to the bimetallic center of the catalytic subunit 1
Gene Name:: MT-CO2
Uniprot ID:: P00403
Molecular weight:: 25564.7

Showing Compound Card for Isocannflavin B (CDB000745)

Structure for CDB000745 (Isocannflavin B)

Enzymes