Showing Compound 2-Feruloyl-1-sinapoylgentiobiose (FDB002177)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:16 UTC

Update date

2020-02-24 19:10:26 UTC

Primary ID

FDB002177

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

2-Feruloyl-1-sinapoylgentiobiose

Description

2-Feruloyl-1-sinapoylgentiobiose belongs to the class of organic compounds known as hydroxycinnamic acid glycosides. These are glycosylated hydoxycinnamic acids derivatives. 2-Feruloyl-1-sinapoylgentiobiose is found, on average, in the highest concentration within broccolis (Brassica oleracea var. italica). 2-Feruloyl-1-sinapoylgentiobiose has also been detected, but not quantified in, brassicas. This could make 2-feruloyl-1-sinapoylgentiobiose a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 2-Feruloyl-1-sinapoylgentiobiose.

CAS Number

Not Available

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
2-Feruloyl-1-sinapoylgentiobiose	db_source
4,5-Dihydroxy-3-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl (2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoic acid	HMDB

Showing 1 to 2 of 2 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.37 g/L	ALOGPS
logP	0.88	ALOGPS
logP	0.28	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	9.19	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	269.82 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	170.82 m³·mol⁻¹	ChemAxon
Polarizability	72.81 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Chemical Formula

C33H40O18

IUPAC name

4,5-dihydroxy-3-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl (2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate

InChI Identifier

InChI=1S/C33H40O18/c1-44-18-10-15(4-7-17(18)35)5-8-23(36)50-31-29(42)27(40)22(14-47-32-30(43)28(41)26(39)21(13-34)48-32)49-33(31)51-24(37)9-6-16-11-19(45-2)25(38)20(12-16)46-3/h4-12,21-22,26-35,38-43H,13-14H2,1-3H3/b8-5+,9-6+

InChI Key

QYKVHEQRAXPEEL-XVYDYJIPSA-N

Isomeric SMILES

COC1=CC(\C=C\C(=O)OC2OC(COC3OC(CO)C(O)C(O)C3O)C(O)C(O)C2OC(=O)\C=C\C2=CC(OC)=C(O)C=C2)=CC(OC)=C1O

Average Molecular Weight

724.6599

Monoisotopic Molecular Weight

724.221464476

Classification

Description

Belongs to the class of organic compounds known as hydroxycinnamic acid glycosides. These are glycosylated hydoxycinnamic acids derivatives.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Hydroxycinnamic acid glycosides

Alternative Parents

Substituents

Hydroxycinnamic acid glycoside
O-cinnamoyl glycoside
Cinnamic acid ester
Coumaric acid or derivatives
O-glycosyl compound
Glycosyl compound
Disaccharide
M-dimethoxybenzene
Dimethoxybenzene
Methoxyphenol
Phenol ether
Phenoxy compound
Methoxybenzene
Styrene
Anisole
Fatty acid ester
Alkyl aryl ether
Phenol
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Fatty acyl
Benzenoid
Oxane
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Carboxylic acid ester
Polyol
Organoheterocyclic compound
Ether
Oxacycle
Acetal
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Carbonyl group
Alcohol
Organooxygen compound
Organic oxygen compound
Primary alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant

Biological location:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	C 54.70%; H 5.56%; O 39.74%	DFC
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	2-Feruloyl-1-sinapoylgentiobiose, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0a4i-3940032300-258f6d833b48ddadcb57	Spectrum
Predicted GC-MS	2-Feruloyl-1-sinapoylgentiobiose, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2-Feruloyl-1-sinapoylgentiobiose, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2-Feruloyl-1-sinapoylgentiobiose, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2-Feruloyl-1-sinapoylgentiobiose, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2-Feruloyl-1-sinapoylgentiobiose, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2-Feruloyl-1-sinapoylgentiobiose, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2-Feruloyl-1-sinapoylgentiobiose, TMS_1_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2-Feruloyl-1-sinapoylgentiobiose, TMS_1_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2-Feruloyl-1-sinapoylgentiobiose, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2-Feruloyl-1-sinapoylgentiobiose, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2-Feruloyl-1-sinapoylgentiobiose, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2-Feruloyl-1-sinapoylgentiobiose, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2-Feruloyl-1-sinapoylgentiobiose, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2-Feruloyl-1-sinapoylgentiobiose, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2-Feruloyl-1-sinapoylgentiobiose, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2-Feruloyl-1-sinapoylgentiobiose, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2-Feruloyl-1-sinapoylgentiobiose, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2-Feruloyl-1-sinapoylgentiobiose, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2-Feruloyl-1-sinapoylgentiobiose, TMS_2_11, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2-Feruloyl-1-sinapoylgentiobiose, TMS_2_12, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2-Feruloyl-1-sinapoylgentiobiose, TMS_2_13, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2-Feruloyl-1-sinapoylgentiobiose, TMS_2_14, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2-Feruloyl-1-sinapoylgentiobiose, TMS_2_15, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2-Feruloyl-1-sinapoylgentiobiose, TMS_2_16, 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	splash10-056r-0491040300-146ab4f3a8a5fd83f528	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-056r-0892020000-af7ce0807f84d72071b4	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-056r-2956010100-bdd1713b2447fea04728	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0ab9-0490110100-00073d3729fe2dc32660	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-05bf-0941010100-af946ddf7b7874120542	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004l-1920000000-0d221c5a414136a3d50e	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0590120500-f7ea5bee50b8c088d512	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0pb9-2730269200-25e129d57b01ca8a96f8	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a5i-4520129100-ada21554306ce9f1f21c	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-056r-0731043900-6d3c3eedd1f15c71ce0b	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0910020000-1255266a9c2a126067e1	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-002b-2913154000-91d38a7eeae79f6edbaa	2021-09-24	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

510

DrugBank ID

Not Available

HMDB ID

HMDB30334

CRC / DFC (Dictionary of Food Compounds) ID

CPD88-P:CGO84-D

EAFUS ID

Not Available

Dr. Duke ID

Not Available

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

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Food	Content Range	Average	Reference

Broccoli	1.316 - 1.316 mg/100 g	1.316 mg/100 g	PHENOL EXPLORER, PHYTOHUB

Showing 1 to 1 of 1 entries

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

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

— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.

Showing Compound 2-Feruloyl-1-sinapoylgentiobiose (FDB002177)

Structure for FDB002177 (2-Feruloyl-1-sinapoylgentiobiose)