ChemFOnt: Showing chemical card for (+)-Dehydrovomifoliol (CFc000282338)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:34:35 UTC

Chemfont ID

CFc000282338

Molecule Identification

Common Name

(+)-Dehydrovomifoliol

Definition

(+)-dehydrovomifoliol, also known as (6s)-6-hydroxy-3-oxo-alpha-ionone, is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units. Thus, (+)-dehydrovomifoliol is considered to be an isoprenoid lipid molecule (+)-dehydrovomifoliol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). (+)-dehydrovomifoliol can be found in rice, which makes (+)-dehydrovomifoliol a potential biomarker for the consumption of this food product.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(4S)-4-Hydroxy-3,5,5-trimethyl-4-[(1E)-3-oxobut-1-enyl]cyclohex-2-en-1-one	ChEBI
(6R)-6-Hydroxy-3-oxo-alpha-ionone	ChEBI
(6S)-6-Hydroxy-3-oxo-alpha-ionone	ChEBI
Dehydrovomifoliol	ChEBI
(6R)-6-Hydroxy-3-oxo-a-ionone	Generator
(6R)-6-Hydroxy-3-oxo-α-ionone	Generator
(6S)-6-Hydroxy-3-oxo-a-ionone	Generator
(6S)-6-Hydroxy-3-oxo-α-ionone	Generator

Chemical Formula

C₁₃H₁₈O₃

Average Molecular Weight

222.284

Monoisotopic Molecular Weight

222.12559444

IUPAC Name

(4S)-4-hydroxy-3,5,5-trimethyl-4-[(1E)-3-oxobut-1-en-1-yl]cyclohex-2-en-1-one

Traditional Name

dehydrovomifoliol

CAS Registry Number

15764-81-5

SMILES

[H]\C(=C(\[H])[C@@]1(O)C(C)=CC(=O)CC1(C)C)C(C)=O

InChI Identifier

InChI=1S/C13H18O3/c1-9-7-11(15)8-12(3,4)13(9,16)6-5-10(2)14/h5-7,16H,8H2,1-4H3/b6-5+/t13-/m1/s1

InChI Key

JJRYPZMXNLLZFH-URWSZGRFSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Megastigmane sesquiterpenoid
Cyclofarsesane sesquiterpenoid
Ionone derivative
Cyclohexenone
Acryloyl-group
Enone
Alpha,beta-unsaturated ketone
Tertiary alcohol
Ketone
Cyclic ketone
Organic oxide
Organic oxygen compound
Organooxygen compound
Alcohol
Hydrocarbon derivative
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

dehydrovomifoliol (CHEBI:4372 )
Cyclofarnesane sesquiterpenoids (C02533 )
Cyclofarnesane sesquiterpenoids (LMPR0103050009 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0302822)

Food

Cereal and cereal product

Cereal

Rice (FooDB: FOOD00125)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.55 g/L	ALOGPS
logP	1.41	ALOGPS
logP	1.65	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	13.37	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	63.93 m³·mol⁻¹	ChemAxon
Polarizability	24.15 Å³	ChemAxon
Number of Rings	1	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

HMDB0302822

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB006379

KNApSAcK ID

Not Available

Chemspider ID

599941

KEGG Compound ID

C02533

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

688492

PDB ID

Not Available

ChEBI ID

4372

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for (+)-Dehydrovomifoliol (CFc000282338)

MOL for CFc000282338 ((+)-Dehydrovomifoliol)

3D MOL for CFc000282338 ((+)-Dehydrovomifoliol)

3D SDF for CFc000282338 ((+)-Dehydrovomifoliol)

3D-SDF for CFc000282338 ((+)-Dehydrovomifoliol)

PDB for CFc000282338 ((+)-Dehydrovomifoliol)

3D PDB for CFc000282338 ((+)-Dehydrovomifoliol)

SMILES for CFc000282338 ((+)-Dehydrovomifoliol)

INCHI for CFc000282338 ((+)-Dehydrovomifoliol)

Structure for CFc000282338 ((+)-Dehydrovomifoliol)

3D Structure for CFc000282338 ((+)-Dehydrovomifoliol)