AFCDB: Vitexin 2''-rhamnoside (FDB021638)

Record Information

Version

1.0

Creation date

2011-03-17 23:25:19 UTC

Update date

2019-11-26 03:20:38 UTC

Primary ID

FDB021638

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Vitexin 2''-rhamnoside

Description

Vitexin 2''-rhamnoside 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 2''-rhamnoside is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Vitexin 2''-rhamnoside can be found in oat and soy bean, which makes vitexin 2''-rhamnoside a potential biomarker for the consumption of these food products.

CAS Number

64820-99-1

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	3.82 g/L	ALOGPS
logP	-0.1	ALOGPS
logP	-0.77	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	6.2	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	236.06 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	136.9 m³·mol⁻¹	ChemAxon
Polarizability	56.25 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	No	ChemAxon

Chemical Formula

C27H30O14

IUPAC name

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

InChI Identifier

InChI=1S/C27H30O14/c1-9-19(33)21(35)23(37)27(38-9)41-26-22(36)20(34)16(8-28)40-25(26)18-13(31)6-12(30)17-14(32)7-15(39-24(17)18)10-2-4-11(29)5-3-10/h2-7,9,16,19-23,25-31,33-37H,8H2,1H3

InChI Key

LYGPBZVKGHHTIE-UHFFFAOYSA-N

Isomeric SMILES

CC1OC(OC2C(O)C(O)C(CO)OC2C2=C3OC(=CC(=O)C3=C(O)C=C2O)C2=CC=C(O)C=C2)C(O)C(O)C1O

Average Molecular Weight

578.5187

Monoisotopic Molecular Weight

578.163555668

Classification

Description

Belongs to the class of organic compounds known as dimethoxybenzenes. These are organic aromatic compounds containing a monocyclic benzene moiety carrying exactly two methoxy groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Methoxybenzenes

Direct Parent

Dimethoxybenzenes

Alternative Parents

Substituents

Dimethoxybenzene
O-dimethoxybenzene
Phenethylamine
Anisole
Phenoxy compound
Phenol ether
Alkyl aryl ether
Fluorobenzene
Halobenzene
Aralkylamine
Piperidine
Aryl fluoride
Aryl halide
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Azacycle
Organoheterocyclic compound
Ether
Aromatic alcohol
Organofluoride
Organohalogen compound
Amine
Alcohol
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Organopnictogen compound
Organic nitrogen compound
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

No ontology term

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	solid
Physical Description	Yellow needles	DFC
Mass Composition	C 56.06%; H 5.23%; O 38.72%	DFC
Melting Point	Mp 213-215? (199-201?)	DFC
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	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Not Available

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - 6V, Negative	splash10-004i-0023190000-796862dfcf4c21af0ce2	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0006-0390000000-134fbd31cad19f47ce84	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0006-0091000000-6b9ccef35a90975b6482	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-004i-0000190000-b428fea920672d9ab217	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0006-0390000000-a15ab514b78dd6261b6a	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-004i-0000190000-6cd3d564ff8b2c9e569f	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-003r-1018920000-2770f9f9deaf21246a33	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0006-0091100000-75afa092c2ae676c22bc	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0000190000-8f9af0b4f3958f1509c9	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-003r-0000980000-48eaa0e05de3c34e333c	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-01r6-0091560000-e2af7b2e426c585504ce	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-01r6-0091550000-9cb990dbbe59fb2d1b7e	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0006-0091000000-6a556ef8e99f7fd03485	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-01r6-0091450000-801df522738531c95642	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0006-0490000000-df874afad6eb37bcb46d	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0001910000-c48ebaf0d779a69db984	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-004i-0000290000-a88959cb424ee4ec2be9	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-003r-1018920000-9aa301ce7ade3d8aa19f	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-02cr-0100970000-ea17dde6c25d4a80ad38	2019-02-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0159-0200910000-f3c0a7007e4680b20885	2019-02-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05nb-2296500000-1ace7d7801def82f7070	2019-02-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-2110690000-f655e8fb8df77a788cf7	2019-02-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-08gl-5514930000-13570e77ba8086e4073f	2019-02-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03dl-8928400000-307281dcc60eae96e09f	2019-02-23	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

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

CMC90-K:KRL99-F

EAFUS ID

Not Available

Dr. Duke ID

VITEXIN-2"-O-ALPHA-L-RHAMNOSIDE|VITEXIN-2"-RHAMNOSIDE|VITEXIN-2"-O-RHAMNOSIDE

BIGG ID

Not Available

KNApSAcK ID

Not Available

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
cancer preventive	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).

Vitexin 2''-rhamnoside (FDB021638)

Structure for FDB021638 (Vitexin 2''-rhamnoside)