Showing Compound 5,6-Epoxy-7-megastigmen-9-one (FDB013585)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:48 UTC

Update date

2019-11-26 03:08:40 UTC

Primary ID

FDB013585

Secondary Accession Numbers

FDB013586

Chemical Information

FooDB Name

5,6-Epoxy-7-megastigmen-9-one

Description

(5r,6s)-5,6-epoxy-7-megastigmen-9-one, also known as 5,6-epoxy-beta-ionone, is a member of the class of compounds known as oxepanes. Oxepanes are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms (5r,6s)-5,6-epoxy-7-megastigmen-9-one is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). (5r,6s)-5,6-epoxy-7-megastigmen-9-one can be found in garden tomato and root vegetables, which makes (5r,6s)-5,6-epoxy-7-megastigmen-9-one a potential biomarker for the consumption of these food products.

CAS Number

23267-57-4

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Showing 1 to 3 of 3 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.048 g/L	ALOGPS
logP	3.2	ALOGPS
logP	2.8	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	19.83	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	29.6 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	60.55 m³·mol⁻¹	ChemAxon
Polarizability	23.95 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C13H20O2

IUPAC name

(3E)-4-{2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}but-3-en-2-one

InChI Identifier

InChI=1S/C13H20O2/c1-10(14)6-9-13-11(2,3)7-5-8-12(13,4)15-13/h6,9H,5,7-8H2,1-4H3/b9-6+

InChI Key

ZTJZJYUGOJYHCU-RMKNXTFCSA-N

Isomeric SMILES

CC(=O)\C=C\C12OC1(C)CCCC2(C)C

Average Molecular Weight

208.2967

Monoisotopic Molecular Weight

208.146329884

Classification

Description

Belongs to the class of organic compounds known as oxepanes. Oxepanes are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Oxepanes

Sub Class

Not Available

Direct Parent

Oxepanes

Alternative Parents

Substituents

Oxepane
Alpha,beta-unsaturated ketone
Enone
Acryloyl-group
Ketone
Oxacycle
Ether
Oxirane
Dialkyl ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant

Biological location:

Cell and elements:

Extracellular

Subcellular:

Process

Naturally occurring process:

Biological process:

Cellular process:

Cell signaling

Role

Industrial application:

Biological role:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	C 74.96%; H 9.68%; O 15.36%	DFC
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	5,6-Epoxy-7-megastigmen-9-one, non-derivatized, GC-MS Spectrum	splash10-00di-3900000000-642601a39cf4828a95cc	Spectrum
GC-MS	5,6-Epoxy-7-megastigmen-9-one, non-derivatized, GC-MS Spectrum	splash10-00di-3900000000-642601a39cf4828a95cc	Spectrum
Predicted GC-MS	5,6-Epoxy-7-megastigmen-9-one, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00kf-9800000000-13d41ca061e64c920db9	Spectrum
Predicted GC-MS	5,6-Epoxy-7-megastigmen-9-one, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4l-1980000000-ab9ee34d0704e1203f75	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052f-6930000000-677e48043052ae8aa6eb	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05nf-9100000000-c9569a9bf6b01df749fb	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0390000000-25629cabf4557eb256b5	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-1980000000-3ff703712ae234f70567	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0080-3900000000-d31c654648f4308ec251	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-066r-0980000000-30ceab1651a7cfac80dc	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0920000000-c6d7089ea87e89a6ca35	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05g0-0910000000-a61bfd0db05ab7db837b	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-052f-0940000000-3fbf6630fa03ee051c9a	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4l-1970000000-c4f484b79f9008b6e759	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-009f-9300000000-a4b084ffa5ef5aab4e26	2021-09-23	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

Not Available

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

JFM41-W:JFM41-W

EAFUS ID

1808

Dr. Duke ID

BETA-IONONE-EPOXIDE

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

23267-57-4

GoodScent ID

rw1378141

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

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Flavor	Citations
berry	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
fruit	Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
fruity	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
orris	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
powdery	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sweet	Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0 The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
violet	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
wood	Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
woody	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.