Human Metabolome Database: Showing metabocard for Naringenin 4'-O-glucuronide (HMDB0041759)

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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

4.0

Status

Detected but not Quantified

Creation Date

2012-09-12 03:40:58 UTC

Update Date

2020-11-09 23:21:12 UTC

HMDB ID

HMDB0041759

Secondary Accession Numbers

HMDB0029208
HMDB29208
HMDB41759

Metabolite Identification

Common Name

Naringenin 4'-O-glucuronide

Description

Naringenin 4'-O-glucuronide belongs to the class of organic compounds known as flavonoid o-glucuronides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid. Naringenin 4'-O-glucuronide is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2S,3S,4S,5R,6S)-6-[4-(5,7-Dihydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-2-yl)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylate	Generator

Chemical Formula

C₂₁H₂₀O₁₁

Average Molecular Weight

448.3769

Monoisotopic Molecular Weight

448.100561482

IUPAC Name

(2S,3S,4S,5R,6S)-6-[4-(5,7-dihydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-2-yl)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

Traditional Name

(2S,3S,4S,5R,6S)-6-[4-(5,7-dihydroxy-4-oxo-2,3-dihydro-1-benzopyran-2-yl)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

CAS Registry Number

158196-35-1

SMILES

O[C@@H]1[C@@H](O)[C@H](OC2=CC=C(C=C2)C2CC(=O)C3=C(O2)C=C(O)C=C3O)O[C@@H]([C@H]1O)C(O)=O

InChI Identifier

InChI=1S/C21H20O11/c22-9-5-11(23)15-12(24)7-13(31-14(15)6-9)8-1-3-10(4-2-8)30-21-18(27)16(25)17(26)19(32-21)20(28)29/h1-6,13,16-19,21-23,25-27H,7H2,(H,28,29)/t13?,16-,17-,18+,19-,21+/m0/s1

InChI Key

DFIUUCDSSKATFP-DNPGXZAYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as flavonoid o-glucuronides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid O-glucuronides

Alternative Parents

Substituents

Flavonoid-4p-o-glucuronide
Flavanone
5-hydroxyflavonoid
7-hydroxyflavonoid
Hydroxyflavonoid
Flavan
Phenolic glycoside
1-o-glucuronide
O-glucuronide
Glucuronic acid or derivatives
Hexose monosaccharide
Glycosyl compound
Chromone
O-glycosyl compound
Chromane
1-benzopyran
Benzopyran
Phenol ether
Aryl ketone
Phenoxy compound
Aryl alkyl ketone
1-hydroxy-2-unsubstituted benzenoid
Beta-hydroxy acid
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Pyran
Oxane
Benzenoid
Hydroxy acid
Monosaccharide
Monocyclic benzene moiety
Vinylogous acid
Secondary alcohol
Ketone
Acetal
Oxacycle
Organoheterocyclic compound
Polyol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Ether
Alcohol
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Source:

Biological:

Plant

Biological location:

Organ and components:

Biofluid and excreta:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Role

Biological role:

Physical Properties

State

Not Available

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
Water Solubility	1.48 g/L	ALOGPS
logP	0.73	ALOGPS
logP	0.89	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	3.21	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	183.21 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	103.3 m³·mol⁻¹	ChemAxon
Polarizability	42.53 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a59-9127300000-c6835872bfd70e22889b	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-0uka-3062159000-c2aec4f11cbaea5cef50	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00ea-0290700000-5f5ea6b829455c17d870	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05fr-0490000000-4c70573c04a73fd85083	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0kmi-1930000000-008fa0b3097795aaf03a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0fdk-1251900000-16bbf6f0839e8d3fc4c8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-2391200000-e011276b61a2b2625c86	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-5590000000-4a1cbbb1494a41016d74	Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	20853910	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	21736852	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	21736852	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	26269369	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 796	20100371	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 796	18710603	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 796	16810646	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 796	19007165	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029929

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

91312540

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Neveu V, Perez-Jimenez J, Vos F, Crespy V, du Chaffaut L, Mennen L, Knox C, Eisner R, Cruz J, Wishart D, Scalbert A: Phenol-Explorer: an online comprehensive database on polyphenol contents in foods. Database (Oxford). 2010;2010:bap024. doi: 10.1093/database/bap024. Epub 2010 Jan 8. [PubMed:20428313 ]

Showing metabocard for Naringenin 4'-O-glucuronide (HMDB0041759)

Structure for HMDB0041759 (Naringenin 4'-O-glucuronide)