ChemFOnt: Showing chemical card for (S)-4',5,7-Trihydroxy-8-prenylflavanone (CFc000335610)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:28:16 UTC

Chemfont ID

CFc000335610

Molecule Identification

Common Name

(S)-4',5,7-Trihydroxy-8-prenylflavanone

Definition

(s)-4',5,7-trihydroxy-8-prenylflavanone is a member of the class of compounds known as 8-prenylated flavanones. 8-prenylated flavanones are flavanones that features a C5-isoprenoid substituent at the 8-position. Thus, (s)-4',5,7-trihydroxy-8-prenylflavanone is considered to be a flavonoid lipid molecule (s)-4',5,7-trihydroxy-8-prenylflavanone is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). (s)-4',5,7-trihydroxy-8-prenylflavanone can be found in beer, which makes (s)-4',5,7-trihydroxy-8-prenylflavanone a potential biomarker for the consumption of this food product.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₂₀H₂₀O₅

Average Molecular Weight

340.375

Monoisotopic Molecular Weight

340.131073744

IUPAC Name

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

Traditional Name

sophoraflavanone B

CAS Registry Number

53846-50-7

SMILES

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

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

InChI Key

LPEPZZAVFJPLNZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 8-prenylated flavanones. These are flavanones that features a C5-isoprenoid substituent at the 8-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

8-prenylated flavanones

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavanones (LMPK12140279 )

Functional Ontology

Not Available

Exogenous (FooDB: )

Food

Beverage

Fermented beverage

Beer (FooDB: FOOD00268)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.016 g/L	ALOGPS
logP	3.23	ALOGPS
logP	4.56	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	7.69	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	36.38 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0247465

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB012291

KNApSAcK ID

Not Available

Chemspider ID

444597

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

509245

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for (S)-4',5,7-Trihydroxy-8-prenylflavanone (CFc000335610)

MOL for CFc000335610 ((S)-4',5,7-Trihydroxy-8-prenylflavanone)

3D MOL for CFc000335610 ((S)-4',5,7-Trihydroxy-8-prenylflavanone)

3D SDF for CFc000335610 ((S)-4',5,7-Trihydroxy-8-prenylflavanone)

3D-SDF for CFc000335610 ((S)-4',5,7-Trihydroxy-8-prenylflavanone)

PDB for CFc000335610 ((S)-4',5,7-Trihydroxy-8-prenylflavanone)

3D PDB for CFc000335610 ((S)-4',5,7-Trihydroxy-8-prenylflavanone)

SMILES for CFc000335610 ((S)-4',5,7-Trihydroxy-8-prenylflavanone)

INCHI for CFc000335610 ((S)-4',5,7-Trihydroxy-8-prenylflavanone)

Structure for CFc000335610 ((S)-4',5,7-Trihydroxy-8-prenylflavanone)

3D Structure for CFc000335610 ((S)-4',5,7-Trihydroxy-8-prenylflavanone)