Showing Compound Narirutin 4'-glucoside (FDB016688)

Record Information

Version

1.0

Creation date

2010-04-08 22:12:35 UTC

Update date

2019-11-26 03:13:37 UTC

Primary ID

FDB016688

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Narirutin 4'-glucoside

Description

Narirutin 4'-glucoside belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. Narirutin 4'-glucoside is found, on average, in the highest concentration within grapefruit/pummelo hybrids (Citrus paradisi X Citrus maxima). Narirutin 4'-glucoside has also been detected, but not quantified in, citrus. This could make narirutin 4'-glucoside a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Narirutin 4'-glucoside.

CAS Number

17257-22-6

Structure

MOL SDF PDB SMILES InChI

Synonyms

Predicted Properties

Property	Value	Source
Water Solubility	5.04 g/L	ALOGPS
logP	-0.92	ALOGPS
logP	-2.4	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	8.64	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	19	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	304.21 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	166.45 m³·mol⁻¹	ChemAxon
Polarizability	72.86 Å³	ChemAxon
Number of Rings	6	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

C33H42O19

IUPAC name

5-hydroxy-2-(4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-7-[(3,4,5-trihydroxy-6-{[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]methyl}oxan-2-yl)oxy]-3,4-dihydro-2H-1-benzopyran-4-one

InChI Identifier

InChI=1S/C33H42O19/c1-11-22(37)25(40)28(43)31(47-11)46-10-20-24(39)27(42)30(45)33(52-20)49-14-6-15(35)21-16(36)8-17(50-18(21)7-14)12-2-4-13(5-3-12)48-32-29(44)26(41)23(38)19(9-34)51-32/h2-7,11,17,19-20,22-35,37-45H,8-10H2,1H3

InChI Key

KQUWJUNIYQVHCG-UHFFFAOYSA-N

Isomeric SMILES

CC1OC(OCC2OC(OC3=CC4=C(C(=O)CC(O4)C4=CC=C(OC5OC(CO)C(O)C(O)C5O)C=C4)C(O)=C3)C(O)C(O)C2O)C(O)C(O)C1O

Average Molecular Weight

742.68

Monoisotopic Molecular Weight

742.232029132

Classification

Description

Belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-7-O-glycosides

Alternative Parents

Substituents

Flavonoid-7-o-glycoside
5-hydroxyflavonoid
Flavanone
Hydroxyflavonoid
Flavan
Phenolic glycoside
Chromone
Disaccharide
Glycosyl compound
O-glycosyl compound
Chromane
Benzopyran
1-benzopyran
Phenoxy compound
Aryl alkyl ketone
Phenol ether
Aryl ketone
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Oxane
Monocyclic benzene moiety
Vinylogous acid
Secondary alcohol
Ketone
Ether
Acetal
Polyol
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Organooxygen compound
Primary alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Plant

Biological location:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Role

Biological role:

Nutrient

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 53.37%; H 5.70%; O 40.93%	DFC
Melting Point	Mp 189-200°	DFC
Optical Rotation	[a]D -62.6 (c, 0.92 in Py)	DFC

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Narirutin 4'-glucoside, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Narirutin 4'-glucoside, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Narirutin 4'-glucoside, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Narirutin 4'-glucoside, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Narirutin 4'-glucoside, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Narirutin 4'-glucoside, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Narirutin 4'-glucoside, TMS_1_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Narirutin 4'-glucoside, TMS_1_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Narirutin 4'-glucoside, TMS_1_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Narirutin 4'-glucoside, TMS_1_10, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Narirutin 4'-glucoside, TMS_1_11, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Narirutin 4'-glucoside, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Narirutin 4'-glucoside, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Narirutin 4'-glucoside, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Narirutin 4'-glucoside, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Narirutin 4'-glucoside, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Narirutin 4'-glucoside, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Narirutin 4'-glucoside, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Narirutin 4'-glucoside, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Narirutin 4'-glucoside, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Narirutin 4'-glucoside, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Narirutin 4'-glucoside, TMS_2_11, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Narirutin 4'-glucoside, TMS_2_12, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Narirutin 4'-glucoside, TMS_2_13, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Narirutin 4'-glucoside, TMS_2_14, 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	splash10-02dr-0250980700-f55e78ea75927a165536	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0490730000-12bbf6f4baf1cfafb18b	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-0890310100-35960c75e761ab4cc52c	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-4622660900-9418ef8dad17ab5b8d4f	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03l1-4942750400-9fdd745f59241e62e042	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0459-4493510000-582b88fc33391d45ffd3	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000l-0000890400-95f46f411e3bfb8bda76	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0100920000-d5a4c1041a6396d06c54	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f79-0800900000-e13e9d51567a0da3ad8b	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0000300900-1dde616d6423c5a1a5e8	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001l-0100900700-8a7a72ec9fe34b170bed	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0f89-0720900200-924722c091df4bd5acbf	2021-09-23	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

215

DrugBank ID

Not Available

HMDB ID

HMDB37584

CRC / DFC (Dictionary of Food Compounds) ID

BFM77-B:KSJ52-J

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

C00008386

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

Grapefruit/Pummelo hybrid	1.233 - 1.233 mg/100 g	1.233 mg/100 g	PHENOL EXPLORER

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 Narirutin 4'-glucoside (FDB016688)

Structure for FDB016688 (Narirutin 4'-glucoside)