Showing Compound (E,E)-Trichostachine (FDB000444)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:34 UTC

Update date

2020-02-24 19:10:07 UTC

Primary ID

FDB000444

Secondary Accession Numbers

FDB006600
FDB011991

Chemical Information

FooDB Name

(E,E)-Trichostachine

Description

(E,E)-Trichostachine, also known as 1-piperoylpyrrolidine, belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms (E,E)-Trichostachine has been detected, but not quantified in, herbs and spices and pepper (spice). This could make (e,e)-trichostachine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (E,E)-Trichostachine.

CAS Number

25924-78-1

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
Trichostachine	Kegg
(2E,4E)-5-(1,3-Benzodioxol-5-yl)-1-(1-pyrrolidinyl)-2,4-pentadien-1-one	MeSH
1-Piperoylpyrrolidine	MeSH
1-Piperoyl-(e,e)-pyrrolidine	HMDB
Pyrrolidine, 1-piperoyl-, (E,E)-	biospider

Predicted Properties

Property	Value	Source
Water Solubility	0.44 g/L	ALOGPS
logP	3.01	ALOGPS
logP	2.33	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Basic)	2.07	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	38.77 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	78.3 m³·mol⁻¹	ChemAxon
Polarizability	29.96 Å³	ChemAxon
Number of Rings	3	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

C16H17NO3

IUPAC name

(2E,4E)-5-(2H-1,3-benzodioxol-5-yl)-1-(pyrrolidin-1-yl)penta-2,4-dien-1-one

InChI Identifier

InChI=1S/C16H17NO3/c18-16(17-9-3-4-10-17)6-2-1-5-13-7-8-14-15(11-13)20-12-19-14/h1-2,5-8,11H,3-4,9-10,12H2/b5-1+,6-2+

InChI Key

GQIJYUMTOUBHSH-IJIVKGSJSA-N

Isomeric SMILES

O=C(\C=C\C=C\C1=CC=C2OCOC2=C1)N1CCCC1

Average Molecular Weight

271.3111

Monoisotopic Molecular Weight

271.120843415

Classification

Description

Belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzodioxoles

Sub Class

Not Available

Direct Parent

Benzodioxoles

Alternative Parents

Substituents

Benzodioxole
N-acylpyrrolidine
Styrene
Benzenoid
Pyrrolidine
Tertiary carboxylic acid amide
Carboxamide group
Acetal
Carboxylic acid derivative
Oxacycle
Azacycle
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organic nitrogen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

benzodioxoles (CHEBI:9691 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Plant

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 70.83%; H 6.32%; N 5.16%; O 17.69%	DFC
Melting Point	Mp 143-145°	DFC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	(E,E)-Trichostachine, non-derivatized, GC-MS Spectrum	splash10-0fk9-0290000000-e92fc9516c43a7ad9514	Spectrum
GC-MS	(E,E)-Trichostachine, non-derivatized, GC-MS Spectrum	splash10-0fk9-0290000000-e92fc9516c43a7ad9514	Spectrum
Predicted GC-MS	(E,E)-Trichostachine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0fkc-5390000000-7bfda9369e555bb06d54	Spectrum
Predicted GC-MS	(E,E)-Trichostachine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-0udi-0950000000-9f2d88b978f2237a85eb	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-0udi-0950000000-9f2d88b978f2237a85eb	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-2290000000-76c18ea5a1e2c576a5c6	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-7970000000-51fe56f246b2ec5bcfd4	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00dl-9400000000-afe354c3cddf61b9ca10	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0090000000-f50f2646b634026f3fce	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-7390000000-37c90a22e5a28a53acdc	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-9200000000-f330d100a34c7f7d5f46	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0090000000-0ebdc69de0cc3f27706a	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-1490000000-41beceda8fe1f339c740	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00dr-6920000000-1c0a5bf853f9d1356bb8	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0090000000-19dbfadd3d4c17868278	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0290000000-6470a49610102798f868	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014m-0590000000-1f0196154dc55f844b03	2021-09-22	View Spectrum