PhytoHub: Showing entry for 8-Prenylnaringenin

8-Prenylnaringenin

Identification

PhytoHub ID

PHUB000373

Name

8-Prenylnaringenin

Systematic Name

Not Available

Synonyms

5,7,4'-Trihydroxy-8-prenylflavanone
Isobavachin

CAS Number

Not Available

Average Mass

340.375

Monoisotopic Mass

340.131073744

Chemical Formula

C₂₀H₂₀O₅

IUPAC Name

(2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-4-one

InChI Key

LPEPZZAVFJPLNZ-SFHVURJKSA-N

InChI Identifier

InChI=1S/C20H20O5/c1-11(2)3-8-14-15(22)9-16(23)19-17(24)10-18(25-20(14)19)12-4-6-13(21)7-5-12/h3-7,9,18,21-23H,8,10H2,1-2H3/t18-/m0/s1

SMILES

CC(C)=CCC1=C2O[C@@H](CC(=O)C2=C(O)C=C1O)C1=CC=C(O)C=C1

Structure

Similar Structures

Calculated Properties

Solubility (ALOGPS): 1.55e-02 g/l
LogS (ALOGPS): -4.34
LogP (ALOGPS): 3.23
Hydrogen Acceptors: 5
Hydrogen Donors: 3
Rotatable Bond Count: 3
Polar Surface Area: 86.99000000000001
Refractivity: 95.53260000000002
Polarizability: 35.073102711338265
Formal Charge: 0
Physiological Charge: 0
pKa (strongest basic): -4.960717116113241
pKa (strongest acidic): 7.690620154617847
Number of Rings: 3
Rule of Five: Yes
Bioavailability: Yes
Ghose Filter: Yes
Veber's Rule: No
MDDR-like Rule: No

External Links

PubChem: 509245
Chemistry Dashboard: DTXSID00333502
Phenol-Explorer: 221
FooDB (Compounds): FDB012291

Taxonomy as Food Phytochemical

Family: Polyphenols
Class: Flavonoids
Sub-class: Miscellaneous flavonoids

Taxonomy as Metabolite

Metabolite Family: (Poly)phenol metabolites
Metabolite Class: Flavonoid metabolites
Metabolite Sub-class: Not Available

Taxonomy of its Food Phytochemical Precursor(s)

Food Phytochemical	Family	Class	Sub-class
Xanthohumol	Polyphenols	Miscellaneous polyphenols	Not Available	Show Food Phytochemical
Isoxanthohumol	Polyphenols	Flavonoids	Miscellaneous flavonoids	Show Food Phytochemical

Classyfire Taxonomy

Kingdom Name: Organic compounds
Class: Flavonoids
Super-class: Phenylpropanoids and polyketides
Sub-class: Flavans
Direct Parent Name: 8-prenylated flavanones
Alternative Parent Names: ["1-hydroxy-2-unsubstituted benzenoids", "4'-hydroxyflavonoids", "5-hydroxyflavonoids", "7-hydroxyflavonoids", "Alkyl aryl ethers", "Aryl alkyl ketones", "Benzene and substituted derivatives", "Chromones", "Flavanones", "Hydrocarbon derivatives", "Organic oxides", "Oxacyclic compounds", "Vinylogous acids"]
External Descriptor Annotations: ["flavanones", "trihydroxyflavanone"]
Substituent Names: ["1-benzopyran", "1-hydroxy-2-unsubstituted benzenoid", "4'-hydroxyflavonoid", "5-hydroxyflavonoid", "7-hydroxyflavonoid", "8-prenylated flavanone", "Alkyl aryl ether", "Aromatic heteropolycyclic compound", "Aryl alkyl ketone", "Aryl ketone", "Benzenoid", "Benzopyran", "Chromane", "Chromone", "Ether", "Flavanone", "Hydrocarbon derivative", "Hydroxyflavonoid", "Ketone", "Monocyclic benzene moiety", "Organic oxide", "Organic oxygen compound", "Organoheterocyclic compound", "Organooxygen compound", "Oxacycle", "Phenol", "Vinylogous acid"]

Spectra from Online Resources

No spectra information available

Food Sources

	Name	Group
	Beer	Beverages, Alcoholic	Publications	Show

Food Sources of its Food Phytochemical(s)

	Food Phytochemical	Food Source	Food Source Group
	Xanthohumol	Beer	Beverages, Alcoholic	Publications	Show
	Isoxanthohumol	Beer	Beverages, Alcoholic	Publications	Show

Role as Biomarker of intake

No roles as Biomarker of intake found

Metabolism

	Food Phytochemical		Metabolite	Species	Biofluids	Origin	TMax	CMax	Urinary Excretion	Formula	Monoisotopic mass
	Xanthohumol		8-Prenylnaringenin	human	plasma	host-gut microbiota co-metabolite	Not Available	Not Available	Not Available	C₂₀H₂₀O₅	340.131073744		Publications
	Isoxanthohumol		8-Prenylnaringenin	rat	plasma, urine	Not Available	Not Available	Not Available	Not Available	C₂₀H₂₀O₅	340.131073744		Publications

Inter-Individual Variations in Metabolism

	Food Phytochemical		Metabolite	Effect	Value

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Showing entry for 8-Prenylnaringenin