Cannabis Compound Database: Showing Compound Card for Isovitexin (CDB000739)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (14) Show 31 proteins XML

Record Information

Version

1.0

Created at

2020-03-19 00:54:11 UTC

Updated at

2020-12-07 19:07:44 UTC

CannabisDB ID

CDB000739

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Isovitexin

Description

Isovitexin, also known as homovitexin, apigenin 8-C-glucoside, saponaretin or beta-D-isovitexin, belongs to the class of organic compounds known as flavonoid C-glycosides. Flavonoid C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone. Isovitexin, which is an isomer of vitexin, is also described as an apigenin flavone glucoside. It can be found in the passionflower, Cannabis, the a‚àö√üa‚àö‚â† palm, mimosa, wheat leaves, and rice hulls of Oryza sativa (PMID: 6991645 ). Isovitexin is an active component in many traditional Chinese medicines and it is also one of 23 flavonoids that have been identified in cannabis plants (PMID: 6991645 ). Isovitexin has shown a wide range of pharmacological effects, such as antioxidant, anti-cancer, anti-inflammatory, anti-hyperalgesic, and neuroprotective effects (PMID: 27693342 ). Isovitexin helps to stimulate apoptotic cell death and autophagy of various cancer cells through the upstream regulation of Bax, PARP, p-JNK, and MAPK and the downstream regulation of the caspases Bcl-2 and ERK1/2.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
6-C-Glucosylapigenin	ChEBI
6-Glucosylapigenin	ChEBI
Apigenin 6-C-glucoside	ChEBI
Apigenin-6-C-glucoside	ChEBI
beta-D-Isovitexin	ChEBI
Saponaretin	ChEBI
b-D-Isovitexin	Generator
Β-D-isovitexin	Generator
6-Glucosyl-apigenin	MeSH
Homovitexin	PhytoBank
6-beta-D-Glucopyranosyl-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one	PhytoBank
6-β-D-Glucopyranosyl-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one	PhytoBank
6-C-beta-D-Glucopyranosylapigenin	PhytoBank
6-C-β-D-Glucopyranosylapigenin	PhytoBank
Apigenin 6-C-beta-D-glucoside	PhytoBank
Apigenin 6-C-β-D-glucoside	PhytoBank
Apigenin 6-C-beta-glucopyranoside	PhytoBank
Apigenin 6-C-β-glucopyranoside	PhytoBank
Apigenin-6-C-beta-D-glucopyranoside	PhytoBank
Apigenin-6-C-β-D-glucopyranoside	PhytoBank
Isoavroside	PhytoBank

Chemical Formula

C₂₁H₂₀O₁₀

Average Molecular Weight

432.38

Monoisotopic Molecular Weight

432.1056

IUPAC Name

5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one

Traditional Name

isovitexin

CAS Registry Number

61838-34-4

SMILES

OC[C@H]1O[C@H]([C@H](O)[C@@H](O)[C@@H]1O)C1=C(O)C2=C(OC(=CC2=O)C2=CC=C(O)C=C2)C=C1O

InChI Identifier

InChI=1S/C21H20O10/c22-7-14-17(26)19(28)20(29)21(31-14)16-11(25)6-13-15(18(16)27)10(24)5-12(30-13)8-1-3-9(23)4-2-8/h1-6,14,17,19-23,25-29H,7H2/t14-,17-,19+,20-,21+/m1/s1

InChI Key

MYXNWGACZJSMBT-VJXVFPJBSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 6-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C6 atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

6-O-methylated flavonoids

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

trihydroxyflavone (CHEBI:66103 )
dimethoxyflavone (CHEBI:66103 )
Flavones and Flavonols (LMPK12111235 )

Ontology

Role

Industrial application:

Pharmaceutical industry:

Antineoplastic agent:

Anticancer agent

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	0.37	ALOGPS
logP	-0.051	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	6.14	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	177.14 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	106.03 m³·mol⁻¹	ChemAxon
Polarizability	42.47 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Not Available

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 10V, positive	splash10-001i-0000900000-7e8773e6dffdca2e961c	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 20V, positive	splash10-02u0-0019300000-bf1e8c212114257bd52c	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 30V, positive	splash10-03e9-0039000000-cb3b3d5ff1fe66f3e8d0	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 40V, positive	splash10-03e9-0059000000-d7c269cffa08f1db2a33	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 50V, positive	splash10-01q9-0296000000-24d27898fce539d6c57f	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - NA , positive	splash10-01q9-0039300000-e763314082ae66e5e723	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 10V, positive	splash10-001i-0049400000-770c6ade47e7eee59445	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 30V, positive	splash10-01q9-0069000000-bc1f50fe4e8cd5052724	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 50V, positive	splash10-015a-0960000000-de27f2f6c53ef2b932c9	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 10V, negative	splash10-001i-0000900000-189d312716882cab2622	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 20V, negative	splash10-001i-0003900000-0b4998a725ea9d79085d	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 30V, negative	splash10-03dl-0009100000-7d9cb987c1ddb226ec9c	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 40V, negative	splash10-03e9-0059000000-82799a3d9dfe72bc9596	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 50V, negative	splash10-001i-0092000000-6949e8b972ab42b08ab2	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 30V, negative	splash10-03di-0009000000-28d0ea8ae44c76a430bf	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 43V, negative	splash10-03dl-0009000000-d44475245655ad4aedd7	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 14V, negative	splash10-001i-0001900000-9499ee7df6f0a4363047	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 16V, negative	splash10-001i-0003900000-111bf3302482cdf9765b	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 18V, negative	splash10-01q9-0007900000-7df52e75f6796aad4abc	2020-07-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00lr-0001900000-befc1cf568ed659e0e53	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-015a-4324900000-e6a94e47ae288eb8a27f	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-4294000000-b3f38a64e6c632a8265e	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-1011900000-bdbc26b4ba26fb0d7001	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-045c-9256700000-c131102de0dd7b21a5be	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05mp-9362000000-6d40ed50c23c875c82d1	2017-06-28	View Spectrum

NMR

Not Available

Pathways

Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Poly [ADP-ribose] polymerase 1	PARP1	1q41-q42	P09874	details
Mitogen-activated protein kinase 12	MAPK12	22q13.33	P53778	details
Mitogen-activated protein kinase 1	MAPK1	22q11.2\|22q11.21	P28482	details
Mitogen-activated protein kinase 7	MAPK7	17p11.2	Q13164	details
Mitogen-activated protein kinase 3	MAPK3	16p11.2	P27361	details
Mitogen-activated protein kinase 9	MAPK9	5q35	P45984	details
Mitogen-activated protein kinase 13	MAPK13	6p21.31	O15264	details
Mitogen-activated protein kinase 11	MAPK11	22q13.33	Q15759	details
Mitogen-activated protein kinase 4	MAPK4	18q21.2	P31152	details
Mitogen-activated protein kinase 6	MAPK6	15q21	Q16659	details
Mitogen-activated protein kinase 10	MAPK10	4q22.1-q23	P53779	details
Mitogen-activated protein kinase 8	MAPK8	10q11.22	P45983	details
Apoptosis regulator Bcl-2	BCL2	18q21.33\|18q21.3	P10415	details
Mitogen-activated protein kinase 15	MAPK15		Q8TD08	details

Transporters

Not Available

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
Poly [ADP-ribose] polymerase 1	PARP1	1q41-q42	P09874	details

Receptors

Protein Name	Gene Name	Locus	Uniprot ID	Details
Poly [ADP-ribose] polymerase 1	PARP1	1q41-q42	P09874	details
Mitogen-activated protein kinase 12	MAPK12	22q13.33	P53778	details
Mitogen-activated protein kinase 1	MAPK1	22q11.2\|22q11.21	P28482	details
Mitogen-activated protein kinase 7	MAPK7	17p11.2	Q13164	details
Mitogen-activated protein kinase 3	MAPK3	16p11.2	P27361	details
Mitogen-activated protein kinase 9	MAPK9	5q35	P45984	details
Mitogen-activated protein kinase 13	MAPK13	6p21.31	O15264	details
Mitogen-activated protein kinase 11	MAPK11	22q13.33	Q15759	details
Mitogen-activated protein kinase 4	MAPK4	18q21.2	P31152	details
Mitogen-activated protein kinase 6	MAPK6	15q21	Q16659	details
Mitogen-activated protein kinase 10	MAPK10	4q22.1-q23	P53779	details
Mitogen-activated protein kinase 8	MAPK8	10q11.22	P45983	details
Mitogen-activated protein kinase 15	MAPK15		Q8TD08	details
Apoptosis regulator BAX	BAX	19q13.33	Q07812	details

Transcriptional Factors

Protein Name	Gene Name	Locus	Uniprot ID	Details
Poly [ADP-ribose] polymerase 1	PARP1	1q41-q42	P09874	details
Apoptosis regulator BAX	BAX	19q13.33	Q07812	details

Concentrations Data

Not Available

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB000614

KNApSAcK ID

C00001059

Chemspider ID

Not Available

KEGG Compound ID

C01714

BioCyc ID

ISOVITEXIN

BiGG ID

Not Available

Wikipedia Link

Isovitexin

METLIN ID

Not Available

PubChem Compound

162350

PDB ID

Not Available

ChEBI ID

18330

References

General References

Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
He M, Min JW, Kong WL, He XH, Li JX, Peng BW: A review on the pharmacological effects of vitexin and isovitexin. Fitoterapia. 2016 Dec;115:74-85. doi: 10.1016/j.fitote.2016.09.011. Epub 2016 Sep 28. [PubMed:27693342 ]

Only showing the first 10 proteins. There are 31 proteins in total.

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Enzymes

Enzyme Details

1. Poly [ADP-ribose] polymerase 1

General function:: Involved in DNA binding
Specific function:: Involved in the base excision repair (BER) pathway, by catalyzing the poly(ADP-ribosyl)ation of a limited number of acceptor proteins involved in chromatin architecture and in DNA metabolism. This modification follows DNA damages and appears as an obligatory step in a detection/signaling pathway leading to the reparation of DNA strand breaks. Mediates the poly(ADP-ribosyl)ation of APLF and CHFR. Positively regulates the transcription of MTUS1 and negatively regulates the transcription of MTUS2/TIP150. With EEF1A1 and TXK, forms a complex that acts as a T-helper 1 (Th1) cell-specific transcription factor and binds the promoter of IFN-gamma to directly regulate its transcription, and is thus involved importantly in Th1 cytokine production.
Gene Name:: PARP1
Uniprot ID:: P09874
Molecular weight:: 113082.945

Enzyme Details

2. Mitogen-activated protein kinase 12

General function:: Involved in MAP kinase activity
Specific function:: Responds to activation by environmental stress and pro- inflammatory cytokines by phosphorylating downstream targets. Plays a role in myoblast differentiation and also in the down- regulation of cyclin D1 in response to hypoxia in adrenal cells suggesting MAPK12 may inhibit cell proliferation while promoting differentiation
Gene Name:: MAPK12
Uniprot ID:: P53778
Molecular weight:: 41939.8

Enzyme Details

3. Mitogen-activated protein kinase 1

General function:: Involved in MAP kinase activity
Specific function:: Acts as a transcriptional repressor. Binds to a [GC]AAA[GC] consensus sequence. Repress the expression of interferon gamma-induced genes. Seems to bind to the promoter of CCL5, DMP1, IFIH1, IFITM1, IRF7, IRF9, LAMP3, OAS1, OAS2, OAS3 and STAT1. Transcriptional activity is independent of kinase activity
Gene Name:: MAPK1
Uniprot ID:: P28482
Molecular weight:: 41389.3

Enzyme Details

4. Mitogen-activated protein kinase 7

General function:: Involved in MAP kinase activity
Specific function:: Plays a role in various cellular processes such as proliferation, differentiation and cell survival. The upstream activator of MAPK7 is the MAPK kinase MAP2K5. Upon activation, it translocates to the nucleus and phosphorylates various downstream targets including MEF2C. EGF activates MAPK7 through a Ras- independent and MAP2K5-dependent pathway. May have a role in muscle cell differentiation. May be important for endothelial function and maintenance of blood vessel integrity. MAP2K5 and MAPK7 interact specifically with one another and not with MEK1/ERK1 or MEK2/ERK2 pathways
Gene Name:: MAPK7
Uniprot ID:: Q13164
Molecular weight:: 88385.5

Enzyme Details

5. Mitogen-activated protein kinase 3

General function:: Involved in MAP kinase activity
Specific function:: Involved in both the initiation and regulation of meiosis, mitosis, and postmitotic functions in differentiated cells by phosphorylating a number of transcription factors such as ELK-1. Phosphorylates EIF4EBP1; required for initiation of translation. Phosphorylates microtubule-associated protein 2 (MAP2). Phosphorylates SPZ1. Phosphorylates heat shock factor protein 4 (HSF4)
Gene Name:: MAPK3
Uniprot ID:: P27361
Molecular weight:: 43135.2

Enzyme Details

6. Mitogen-activated protein kinase 9

General function:: Involved in MAP kinase activity
Specific function:: JNK2 isoforms display different binding patterns:alpha- 1 and alpha-2 preferentially bind to c-Jun, whereas beta-1 and beta-2 bind to ATF2. However, there is no correlation between binding and phosphorylation, which is achieved at about the same efficiency by all isoforms. JUNB is not a substrate for JNK2 alpha-2, and JUND binds only weakly to it
Gene Name:: MAPK9
Uniprot ID:: P45984
Molecular weight:: 48138.7

Enzyme Details

7. Mitogen-activated protein kinase 13

General function:: Involved in MAP kinase activity
Specific function:: Responds to activation by environmental stress and pro- inflammatory cytokines by phosphorylating downstream targets. Plays a role in the regulation of protein translation by phosphorylating and inactivating EEF2K
Gene Name:: MAPK13
Uniprot ID:: O15264
Molecular weight:: 42089.3

Enzyme Details

8. Mitogen-activated protein kinase 11

General function:: Involved in MAP kinase activity
Specific function:: Kinase involved in a signal transduction pathway that is activated by changes in the osmolarity of the extracellular environment, by cytokines, or by environmental stress. Phosphorylates preferentially transcription factor ATF2
Gene Name:: MAPK11
Uniprot ID:: Q15759
Molecular weight:: 41356.9

Enzyme Details

9. Mitogen-activated protein kinase 4

General function:: Involved in MAP kinase activity
Specific function:: Phosphorylates microtubule-associated protein 2 (MAP2). May promote entry in the cell cycle
Gene Name:: MAPK4
Uniprot ID:: P31152
Molecular weight:: 65921.0

Enzyme Details

10. Mitogen-activated protein kinase 6

General function:: Involved in MAP kinase activity
Specific function:: Phosphorylates microtubule-associated protein 2 (MAP2). May promote entry in the cell cycle
Gene Name:: MAPK6
Uniprot ID:: Q16659
Molecular weight:: 82680.1

Only showing the first 10 proteins. There are 31 proteins in total.

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Showing Compound Card for Isovitexin (CDB000739)

Structure for CDB000739 (Isovitexin)

Enzymes