Showing Compound Germacrone (FDB005347)

Record Information

Version

1.0

Creation date

2010-04-08 22:06:39 UTC

Update date

2019-11-26 03:00:31 UTC

Primary ID

FDB005347

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Germacrone

Description

Germacrone is a member of the class of compounds known as germacrane sesquiterpenoids. Germacrane sesquiterpenoids are sesquiterpenoids having the germacrane skeleton, with a structure characterized by a cyclodecane ring substituted with an isopropyl and two methyl groups. Germacrone is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Germacrone can be found in common thyme and turmeric, which makes germacrone a potential biomarker for the consumption of these food products. Germacrone is an antiviral isolate of Geranium macrorrhizum .

CAS Number

6902-91-6

Structure

MOL SDF PDB SMILES InChI

Synonyms

Predicted Properties

Property	Value	Source
Water Solubility	0.13 g/L	ALOGPS
logP	4.61	ALOGPS
logP	4.11	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	16.77	ChemAxon
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	71.78 m³·mol⁻¹	ChemAxon
Polarizability	25.79 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

C15H22O

IUPAC name

(3E,7E)-3,7-dimethyl-10-(propan-2-ylidene)cyclodeca-3,7-dien-1-one

InChI Identifier

InChI=1S/C15H22O/c1-11(2)14-9-8-12(3)6-5-7-13(4)10-15(14)16/h7-8H,5-6,9-10H2,1-4H3/b12-8+,13-7+

InChI Key

CAULGCQHVOVVRN-SWZPTJTJSA-N

Isomeric SMILES

CC(C)=C1C\C=C(C)\CC\C=C(C)\CC1=O

Average Molecular Weight

218.3346

Monoisotopic Molecular Weight

218.167065326

Classification

Description

Belongs to the class of organic compounds known as germacrane sesquiterpenoids. These are sesquiterpenoids having the germacrane skeleton, with a structure characterized by a cyclodecane ring substituted with an isopropyl and two methyl groups.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Germacrane sesquiterpenoids

Alternative Parents

Substituents

Germacrane sesquiterpenoid
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

No ontology term

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	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Not Available

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0290000000-8ed425ff66adc44e9c6c	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00or-3950000000-f547ccacc1215fbe1a52	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0uxr-9710000000-3bc7bdc6ded24d82632f	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0090000000-24e95fa890525afefe8a	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0390000000-f19cd4784f99d57ea0c8	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0f7c-2910000000-f683e557dedf1065dec4	2016-08-03	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

C16966

Pubchem Compound ID

6436348

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

Not Available

EAFUS ID

Not Available

Dr. Duke ID

GERMACRONE

BIGG ID

Not Available

KNApSAcK ID

C00011728

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

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

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Descriptor	ID	Definition	Reference
analgesic	35480	An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.	DUKE
anti edemic			DUKE
anti inflammatory	35472	A substance that reduces or suppresses inflammation.	DUKE
anti stress	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti tussive	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti ulcer	49201	One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract.	DUKE
hypothermic			DUKE