Livestock Metabolome Database: Showing metabocard for Naringenin (LMDB00406)

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

Record Information

Version

1.0

Creation Date

2016-07-13 19:49:08 UTC

Update Date

2016-09-23 18:45:22 UTC

Lmdb

LMDB00406

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Naringenin

Description

Naringenin (not to be confused with naringin) is a flavanone that is considered to have a bioactive effect on animal health as antioxidant, free radical scavenger, antiinflammatory, carbohydrate metabolism promoter, immunity system modulater. This substance has also been shown to repair DNA. Scientists exposed cells to 80 micomoles of naringenin per liter, for 24 hours, and found that the amount of hydroxyl damage to the DNA was reduced by 24 percent in that very short period of time. Unfortunately, this bioflavonoid is difficult to absorb on oral ingestion. Only 15% of ingested naringenin will get absorbed, in the animal gastrointestinal tract, in the best case scenario. A full glass of orange juice will supply about enough naringenin to achieve a concentration of about 0.5 micromoles per liter. But, one has to wonder, if given more time than 24 hours, would lower concentrations have similar effects. Wikipedia.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(-)-(2S)-Naringenin	ChEBI
(2S)-Naringenin	ChEBI
(S)-2,3-Dihydo-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one	ChEBI
4',5,7-Trihydroxyflavanone	ChEBI
Naringetol	ChEBI
Pelargidanon	ChEBI
Salipurpol	ChEBI
(-)-Naringenin	HMDB
Asahina	HMDB
Naringenine	HMDB
Salipurol	HMDB
(2S)-2,3-Dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one	PhytoBank
(2S)-4',5,7-Trihydroxyflavanone	PhytoBank
(2S)-4’,5,7-Trihydroxyflavanone	PhytoBank
(S)-Naringenin	PhytoBank
S-Dihydrogenistein	PhytoBank
5,7,4'-Trihydroxyflavanone	PhytoBank
5,7,4’-Trihydroxyflavanone	PhytoBank

Chemical Formula

C₁₅H₁₂O₅

Average Molecular Weight

272.2528

Monoisotopic Molecular Weight

272.068473494

IUPAC Name

(2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

naringenin

CAS Registry Number

480-41-1

SMILES

[H][C@]1(CC(=O)C2=C(O1)C=C(O)C=C2O)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C15H12O5/c16-9-3-1-8(2-4-9)13-7-12(19)15-11(18)5-10(17)6-14(15)20-13/h1-6,13,16-18H,7H2/t13-/m0/s1

InChI Key

FTVWIRXFELQLPI-ZDUSSCGKSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as flavanones. Flavanones are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

Flavanones

Alternative Parents

Substituents

Flavanone
Hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Chromone
Benzopyran
Chromane
1-benzopyran
Aryl alkyl ketone
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
Phenol
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Ketone
Organoheterocyclic compound
Oxacycle
Ether
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

naringenin (CHEBI:17846 )
flavanones (C00509 )
Flavanones (LMPK12140001 )

Ontology

Status

Detected but not Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

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
logP	2.47	ALOGPS
logP	2.84	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	7.86	ChemAxon
pKa (Strongest Basic)	-5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	71.29 m³·mol⁻¹	ChemAxon
Polarizability	27.31 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-00fs-1951400000-0e93ea96a72cb2a5a868	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0a4r-2961300000-725a9d843a4286e86b06	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00fs-1951400000-0e93ea96a72cb2a5a868	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4r-2961300000-725a9d843a4286e86b06	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00fs-1951400000-44c9c035aeffcacf4e8c	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-004l-1931100000-ec4d00bbd2895d4d5f9c	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4r-2961300000-6cd5d798a9dad326f771	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-1290000000-3182db290eb43c661919	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-01b9-2531900000-0583af94457df8aad759	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-00di-0190000000-ba73aef4d7cf20a2777d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-066r-3900000000-98ba56d82461a2dc7f6f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-02t9-9600000000-005d5eb55c1f6f3b893d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 5V, Positive	splash10-00di-0090000000-87dba9fe511299bf27e8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 5V, Positive	splash10-00di-0090000000-52282430f89f3cfd51ff	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0g4i-1960000000-74e384d175dd4f05938c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-014i-1900000000-702ce5f0315e56bb08a0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0udi-2900000000-aeb81b324d8162537df3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0fk9-1960000000-b4a541e5476f88624522	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-000i-0090000000-cfa015b97699d9b8d3a9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 25V, Negative	splash10-0gb9-0900000000-5295f7ce31d20a80235c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-0gb9-0900000000-5295f7ce31d20a80235c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 40V, Negative	splash10-0gb9-0900000000-5295f7ce31d20a80235c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-0gb9-0900000000-5295f7ce31d20a80235c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-0gb9-0900000000-5295f7ce31d20a80235c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-0gb9-0900000000-5295f7ce31d20a80235c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-00di-0090000000-dae76236c5699dabc079	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 25V, Negative	splash10-0gb9-0900000000-5295f7ce31d20a80235c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-00di-0090010000-5e9a02398f13b71eccfb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0290000000-32844ab19a143b70951b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0fk9-0980000000-93073e4c39e23c3099c5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0uki-4900000000-8d2daa4eb7a40b866718	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0090000000-b29e35ecf9be0aa440c2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-1390000000-e9112df7c7b29664a011	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014l-6920000000-3b7e4e282dc4008e8c8e	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum