Showing Compound Vitexin (FDB002501)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:24 UTC

Update date

2020-02-24 19:11:06 UTC

Primary ID

FDB002501

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Vitexin

Description

Vitexin is a member of the class of compounds known as flavonoid 8-c-glycosides. Flavonoid 8-c-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to 8-position of a 2-phenylchromen-4-one flavonoid backbone. Vitexin is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Vitexin can be found in a number of food items such as flaxseed, prairie turnip, mung bean, and tree fern, which makes vitexin a potential biomarker for the consumption of these food products. Vitexin is an apigenin flavone glucoside, a chemical compound found in the passion flower, Vitex agnus-castus (chaste tree or chasteberry), in the Phyllostachys nigra bamboo leaves, in the pearl millet (Pennisetum millet), and in Hawthorn .

CAS Number

3681-93-4

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
8-b-D-Glucopyranosyl-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one, 9CI	db_source
8-Glucopyranosyl-4',5,7-trihydroxyflavone	db_source
8-Glucopyranosylapigenin	db_source
8-Glucosylapigenin	db_source
Apigenin 8-C-glucoside	manual
Orientoside	db_source

Predicted Properties

Property	Value	Source
Water Solubility	1.73 g/L	ALOGPS
logP	0.36	ALOGPS
logP	-0.051	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	6.17	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	41.42 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

Chemical Formula

C21H20O10

IUPAC name

5,7-dihydroxy-2-(4-hydroxyphenyl)-8-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one

InChI Identifier

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

InChI Key

SGEWCQFRYRRZDC-UHFFFAOYSA-N

Isomeric SMILES

OCC1OC(C(O)C(O)C1O)C1=C(O)C=C(O)C2=C1OC(=CC2=O)C1=CC=C(O)C=C1

Average Molecular Weight

432.3775

Monoisotopic Molecular Weight

432.10564686

Classification

Description

Belongs to the class of organic compounds known as flavonoid 8-c-glycosides. Flavonoid 8-C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to 8-position of a 2-phenylchromen-4-one flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid 8-C-glycosides

Alternative Parents

Substituents

Flavonoid-8-c-glycoside
Hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavone
Phenolic glycoside
Hexose monosaccharide
Glycosyl compound
C-glycosyl compound
Chromone
1-benzopyran
Benzopyran
Pyranone
Phenol
1-hydroxy-2-unsubstituted benzenoid
Pyran
Monosaccharide
Monocyclic benzene moiety
Benzenoid
Oxane
Heteroaromatic compound
Vinylogous acid
Secondary alcohol
Ether
Dialkyl ether
Organoheterocyclic compound
Oxacycle
Polyol
Primary alcohol
Organic oxide
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Source:

Endogenous

Biological:

Plant

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 58.34%; H 4.66%; O 37.00%	DFC
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	[a]20D -14.5 (c, 2.79 in Py)	DFC
Spectroscopic UV Data	336 () (MeOH)	DFC
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Vitexin, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-003r-2500948000-9602b155e7528f818557	Spectrum
Predicted GC-MS	Vitexin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0089-6398600000-32d47907099e4eb77fde	Spectrum
Predicted GC-MS	Vitexin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Vitexin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Vitexin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Vitexin, TMS_3_19, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Vitexin, TMS_4_23, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Vitexin, TMS_4_25, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Vitexin, TMS_4_26, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Vitexin, TMS_5_17, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Vitexin, TMS_5_18, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Vitexin, TMS_5_19, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Vitexin, TMS_6_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Vitexin, TBDMS_3_19, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Vitexin, TBDMS_4_23, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Vitexin, TBDMS_4_26, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Vitexin, "5,7-dihydroxy-2-(4-hydroxyphenyl)-8-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one,3TMS,#19" TMS, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Vitexin, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Vitexin, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Vitexin, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Vitexin, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Vitexin, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Vitexin, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Vitexin, TMS_1_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Vitexin, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-001i-0003900000-c85af2e6067513ff7b2a	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-001i-0003900000-6f12d68683f1af09bc59	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-001i-0003900000-23a381746616792b88ef	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-014i-0910000000-97e820ce7cc99fd172be	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-01q9-0194000000-fa8b33fb7f7b3d780856	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-02ti-1930000000-677e3bacca878af047c7	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-014i-1920000000-347dc116011ee01fc920	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-01q9-0194000000-adc9deaf16dd2ff40843	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-01q9-0149500000-8286f532e21c42b6dd42	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-03e9-0049400000-3c2074cf667b2392d98a	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-01q9-0049500000-faac86d2153dcec7473a	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-01q9-0194000000-8f3030ecc51bfd13e8ed	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00lr-0001900000-958c99e5dd8f93cb7d84	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-015a-4324900000-09b1bdaa3f1336b36f0a	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000t-5194000000-bca39f308b9ddf54a00b	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-1011900000-a6689e1e349d5b719f2d	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-045c-9256700000-24a4b43d1cb46da46b7d	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05mp-9262000000-72d91a652228e0bd5d48	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0000900000-509ee28ef47ce2bd195a	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0000900000-509ee28ef47ce2bd195a	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0159-0609600000-594b0f20ae3ffca5241a	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0000900000-96b50b9840c4a64e416b	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0000900000-9eea965addbce350e503	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0bt9-0925200000-f5f9c91aef959bf58e00	2021-09-25	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

Not Available

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

262

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

CMC90-K:CMC90-K

EAFUS ID

Not Available

Dr. Duke ID

VITEXIN

BIGG ID

Not Available

KNApSAcK ID

C00001110

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
Angiotensin converting enzyme inhibitor	35457	An agent that blocks the conversion of angiotensin I to angiotensin II, reducing blood pressure and fluid retention. Therapeutically, it's used to treat hypertension, heart failure, and protect kidney function in diabetes, thereby reducing the risk of cardiovascular disease and stroke.	DUKE
Aldose reductase inhibitor	48550	An agent that blocks the activity of aldose reductase, an enzyme involved in glucose metabolism. It reduces oxidative stress and inflammation, commonly used in managing diabetic complications, such as neuropathy, nephropathy, and retinopathy.	DUKE
Anti-arrhythmic	38070	An agent that regulates heart rhythm, correcting irregular heartbeat patterns. Therapeutically, it restores normal cardiac function, commonly used to manage arrhythmias, prevent sudden cardiac death, and treat conditions like atrial fibrillation and ventricular tachycardia.	DUKE
Anti-bradiquinic		An agent that inhibits bradykinin, reducing inflammation and pain. Therapeutically, it's used to treat conditions like hereditary angioedema, and has potential applications in managing pain, inflammation, and allergic reactions.	DUKE
Anti dermatitic	50177	An agent that reduces skin inflammation and irritation, commonly used to treat dermatitis, eczema, and other skin disorders, providing relief from itching, redness, and swelling.	DUKE
Anti histaminic	37956	An agent that blocks histamine receptors, reducing allergic symptoms. Therapeutically, it alleviates itching, sneezing, and runny nose, commonly used in managing allergies, itching, and hives, as well as treating conditions like anaphylaxis and allergic rhinitis.	DUKE
Anti-inflammatory	35472	An agent that reduces inflammation, playing a biological role in suppressing immune responses and therapeutic applications in managing pain, swelling, and redness. Key medical uses include treating arthritis, allergies, and autoimmune disorders, as well as relieving symptoms of conditions such as asthma and dermatitis.	DUKE
Anti-oxidant	22586	An agent that neutralizes free radicals, reducing oxidative stress and cell damage. Its biological role involves protecting cells from harm, and it has therapeutic applications in managing chronic diseases, such as cancer, diabetes, and neurodegenerative disorders, with key medical uses including anti-aging, anti-inflammatory, and cardio protective effects.	DUKE
Anti-serotoninic	48278	An agent that blocks the activity of serotonin, a neurotransmitter involved in mood regulation. It reduces serotonin's effects, commonly used in managing schizophrenia, anxiety disorders, and nausea, as well as treating migraine headaches and irritable bowel syndrome.	DUKE
Anti-thyroid		An agent that inhibits thyroid hormone production, used to treat hyperthyroidism by reducing thyroid hormone levels, commonly applied in managing conditions like Graves' disease.	DUKE
Aphidifuge	25944	An agent that repels aphids, used in agriculture to protect plants. Biologically, it disrupts aphid feeding and reproduction. Therapeutically, it has been explored for its potential insecticidal and antiparasitic properties, with possible applications in managing insect-borne diseases and parasitic infections.	DUKE
cAMP-phosphodiesterase inhibitor	23924	An agent that blocks the breakdown of cyclic adenosine monophosphate (cAMP), increasing its levels and enhancing cellular signaling. Therapeutically, it is used to treat respiratory diseases such as asthma and chronic obstructive pulmonary disease (COPD), as well as certain cardiovascular conditions.	DUKE
Cancer preventive	35610	An agent that inhibits the development and progression of cancer, reducing tumor formation and growth. It plays a biological role in blocking carcinogenic pathways, and has therapeutic applications in chemoprevention. Key medical uses include reducing the risk of cancer in high-risk individuals and preventing cancer recurrence.	DUKE
Goitrogenic		A substance that interferes with thyroid hormone production by blocking iodine uptake, leading to increased TSH release and potential goiter formation, with therapeutic applications in managing hyperthyroidism and certain thyroid disorders.	DUKE
Hypotensive		An agent that lowers blood pressure, playing a biological role in regulating cardiovascular function. Therapeutically, it's used to manage hypertension, heart failure, and angina, with key medical applications in preventing stroke, kidney disease, and cardiac complications.	DUKE
Thyroid-peroxidase inhibitor	23924	An agent that blocks the activity of thyroid peroxidase, an enzyme crucial for thyroid hormone production. It reduces thyroid hormone synthesis, commonly used to treat hyperthyroidism, particularly in conditions like Graves' disease, and to manage thyroid storm.	DUKE
Platelet aggregation inhibitor	50427	An agent that prevents platelets from clumping, reducing blood clot formation. It plays a biological role in preventing thrombosis and is therapeutically used to manage cardiovascular diseases, such as myocardial infarction, stroke, and peripheral artery disease.	CHEBI