ContaminantDB: 6-Prenylnaringenin

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-26 02:09:53 UTC

Update Date

2016-11-09 01:19:08 UTC

Accession Number

CHEM030786

Identification

Common Name

6-Prenylnaringenin

Class

Small Molecule

Description

(S)-4',5,7-Trihydroxy-6-prenylflavanone is found in alcoholic beverages. (S)-4',5,7-Trihydroxy-6-prenylflavanone is isolated from Humulus lupulus (hops).

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
5,7,4'-Trihydroxy-6-prenylflavanone	HMDB
6-Prenylnaringenin	HMDB

Chemical Formula

C₂₀H₂₀O₅

Average Molecular Mass

340.375 g/mol

Monoisotopic Mass

340.131 g/mol

CAS Registry Number

68236-13-5

IUPAC Name

5,7-dihydroxy-2-(4-hydroxyphenyl)-6-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

5,7-dihydroxy-2-(4-hydroxyphenyl)-6-(3-methylbut-2-en-1-yl)-2,3-dihydro-1-benzopyran-4-one

SMILES

CC(C)=CCC1=C(O)C=C2OC(CC(=O)C2=C1O)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C20H20O5/c1-11(2)3-8-14-15(22)9-18-19(20(14)24)16(23)10-17(25-18)12-4-6-13(21)7-5-12/h3-7,9,17,21-22,24H,8,10H2,1-2H3

InChI Key

YHWNASRGLKJRJJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as 6-prenylated flavanones. These are flavanones that features a C5-isoprenoid substituent at the 6-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

6-prenylated flavanones

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.015 g/L	ALOGPS
logP	3.17	ALOGPS
logP	4.56	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	7.67	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	3	ChemAxon
Refractivity	95.53 m³·mol⁻¹	ChemAxon
Polarizability	37.07 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	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	splash10-052f-6479000000-7143fd1ee1bd6f9ca765	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-0006-2400390000-e18b12bc837f90493ce9	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-014i-0940000000-459e8582c8b8f7edd4a9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-000i-0009000000-164e1d0d81349264196b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 40V, Negative	splash10-014i-0900000000-a7f2d42e86f57a481e66	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-014i-0900000000-a7f2d42e86f57a481e66	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-014i-0900000000-a7f2d42e86f57a481e66	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-014i-0940000000-459e8582c8b8f7edd4a9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-000i-0009000000-164e1d0d81349264196b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 40V, Negative	splash10-014i-0900000000-a7f2d42e86f57a481e66	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-000i-0009000000-d427874324ff6ac1c315	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-000i-0029000000-ed90adba71a1bcafaf85	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-014i-0900000000-ecdbdf82de7403141b5d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0009000000-d427874324ff6ac1c315	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-014i-0900000000-a7f2d42e86f57a481e66	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0029000000-ed90adba71a1bcafaf85	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-014i-0940000000-459e8582c8b8f7edd4a9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0249000000-f35282abc190a737aeee	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0600-3694000000-a18b08342b4ff2dfa539	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01b9-3910000000-2e418a09263b237d0baf	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0109000000-f10cfcdb427b712c6047	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-1659000000-b1af31efddfeec198d50	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05xu-2910000000-5a86f4180b10108c31cd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0009000000-b61a6a678d9c858cdfb2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00kr-0179000000-807cf21cbecaa7e175a3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-0900000000-adecca100d2cd8208a8b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0009000000-dd4479d6058cdf87ccc7	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0037247

FooDB ID

FDB016258

Phenol Explorer ID

Not Available

KNApSAcK ID

C00000997

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

2759246

ChEBI ID

Not Available

PubChem Compound ID

3519901

Kegg Compound ID

C09832

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.

6-Prenylnaringenin (CHEM030786)

Structure for CHEM030786: 6-Prenylnaringenin