Showing Compound (3R,8E)-3-Hydroxy-5,8-megastigmadien-7-one (FDB021865)

Record Information

Version

1.0

Creation date

2011-07-19 19:40:38 UTC

Update date

2019-11-26 03:20:59 UTC

Primary ID

FDB021865

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

(3R,8E)-3-Hydroxy-5,8-megastigmadien-7-one

Description

(3R,8E)-3-Hydroxy-5,8-megastigmadien-7-one belongs to the class of organic compounds known as enones. Enones are compounds containing the enone functional group, with the structure RC(=O)CR' (3R,8E)-3-Hydroxy-5,8-megastigmadien-7-one has been detected, but not quantified in, a few different foods, such as blackberries (Rubus), common grapes (Vitis vinifera), and evergreen blackberries (Rubus laciniatus). This could make (3R,8E)-3-hydroxy-5,8-megastigmadien-7-one a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (3R,8E)-3-Hydroxy-5,8-megastigmadien-7-one.

CAS Number

35734-61-3

Structure

MOL SDF PDB SMILES InChI

Synonyms

Predicted Properties

Property	Value	Source
Water Solubility	1.25 g/L	ALOGPS
logP	2.48	ALOGPS
logP	2.66	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	18.91	ChemAxon
pKa (Strongest Basic)	-1.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	63.57 m³·mol⁻¹	ChemAxon
Polarizability	24.3 Å³	ChemAxon
Number of Rings	1	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

(2E)-1-(4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)but-2-en-1-one

InChI Identifier

InChI=1S/C13H20O2/c1-5-6-11(15)12-9(2)7-10(14)8-13(12,3)4/h5-6,10,14H,7-8H2,1-4H3/b6-5+

InChI Key

UPRXEFYRIACHQZ-AATRIKPKSA-N

Isomeric SMILES

C\C=C\C(=O)C1=C(C)CC(O)CC1(C)C

Average Molecular Weight

208.2967

Monoisotopic Molecular Weight

208.146329884

Classification

Description

Belongs to the class of organic compounds known as enones. Enones are compounds containing the enone functional group, with the structure RC(=O)CR'.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Enones

Alternative Parents

Substituents

Enone
Acryloyl-group
Secondary alcohol
Ketone
Organic oxide
Hydrocarbon derivative
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Plant

Biological location:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Role

Industrial application:

Biological role:

Nutrient

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%	CCD
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
Predicted GC-MS	(3R,8E)-3-Hydroxy-5,8-megastigmadien-7-one, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-2900000000-0d1f34f7024058f99a27	Spectrum
Predicted GC-MS	(3R,8E)-3-Hydroxy-5,8-megastigmadien-7-one, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-030c-9570000000-1aadcd929d1bc0b29e24	Spectrum
Predicted GC-MS	(3R,8E)-3-Hydroxy-5,8-megastigmadien-7-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	splash10-052f-0950000000-b2ef7c9cf805d700ec04	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05mo-3910000000-f295865a5316eec3c949	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0abm-9500000000-8f7771c27fbfd854750a	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0390000000-1db45c4005186b8c80f3	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4r-3890000000-5bfd4f84a6ebb1a87a2e	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00ku-5900000000-5c8586f406b0a71d33a2	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0910000000-078d5cb174ea069c9920	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0079-0900000000-36b234393d19ff97cbbb	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-3900000000-f9dbc65df8ba744ea602	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a5i-0930000000-7bec05bbc6d148e2873e	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05ai-3910000000-da814e683647d74b1026	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-4900000000-b8bbbbccaf4ba2c64d97	2021-09-25	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

4926545

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

6420999

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB41636

CRC / DFC (Dictionary of Food Compounds) ID

KHN29-C:KHN30-W

EAFUS ID

Not Available

Dr. Duke ID

3-HYDROXY-BETA-DAMASCONE

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

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

Blackberry	Expected but not quantified	Not Available	Hans-Ulrich Humpf and Peter Schreier. Bound aroma compounds from the fruit and the leaves of blackberry (Rubus laciniata L.) J. Agrie. FoodChem. 1991, 39. 1830-1832 https://pubs.acs.org/doi/pdf/10.1021/jf00010a028
Common grape	Expected but not quantified	Not Available	DUKE