ContaminantDB: (S)-Homostachydrine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-25 23:52:40 UTC

Update Date

2016-11-09 01:18:30 UTC

Accession Number

CHEM027641

Identification

Common Name

(S)-Homostachydrine

Class

Small Molecule

Description

(S)-Homostachydrine (also known as pipecolic acid betaine or homostachydrine) can be found in green coffee beans of Robusta and Arabica species (PMID: 27006213). (S)-Homostachydrine content is unaffected by coffee bean roasting treatment because of its remarkable heat stability. This makes it a good candidate marker for determining the content of Robusta and Arabica species in roasted coffee blends. (S)-Homostachydrine is also a potential marker of coffee consumption as it can be found in both human serum and human urine. It is also found in alfalfa seeds and leaves. More specifically, (S)-homostachydrine can be isolated from the seeds of Medicago sativa (alfalfa) as well as from Achillea millefolium (yarrow). (S)-Homostachydrine is also found in the fruits, seeds, and leaves of orange, lemon, and bergamot (PMID: 22208890).

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical Structure

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

Synonyms

Value	Source
Homostachydrine	HMDB
Pipecolic acid betaine	HMDB
S-Homostachydrine	HMDB
(2S)-1,1-Dimethylpiperidin-1-ium-2-carboxylic acid	Generator

Chemical Formula

C₈H₁₅NO₂

Average Molecular Mass

157.210 g/mol

Monoisotopic Mass

157.110 g/mol

CAS Registry Number

472-22-0

IUPAC Name

(2S)-1,1-dimethylpiperidin-1-ium-2-carboxylate

Traditional Name

homostachydrine

SMILES

C[N+]1(C)CCCC[C@H]1C([O-])=O

InChI Identifier

InChI=1S/C8H15NO2/c1-9(2)6-4-3-5-7(9)8(10)11/h7H,3-6H2,1-2H3/t7-/m0/s1

InChI Key

XULZWQRXYTVUTE-ZETCQYMHSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

L-alpha-amino acids

Alternative Parents

Substituents

L-alpha-amino acid
Piperidinecarboxylic acid
Piperidine
Quaternary ammonium salt
Tetraalkylammonium salt
Carboxylic acid salt
Carboxylic acid
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Azacycle
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Amine
Organic salt
Carbonyl group
Organic nitrogen compound
Hydrocarbon derivative
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Pyrrolidine alkaloids (C08283 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.14 g/L	ALOGPS
logP	-2	ALOGPS
logP	-3.4	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	2.39	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	40.13 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	64.71 m³·mol⁻¹	ChemAxon
Polarizability	16.92 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-08fr-9400000000-687b9b09f0e9c65ca3a9	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0900000000-6d4634868b41a48837ea	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0bt9-2900000000-886043a617d75e47c1c5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0596-9100000000-0617d15a8a0a14a1f151	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-391842ea1e278385a6f1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0900000000-55f9328a9190c2232707	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0ar0-9000000000-6605fc93bf304ad99e07	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0900000000-7b2fe40c81420a678777	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-5900000000-231bcfa989f73c026f39	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9100000000-9e558dde2f341c252059	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-0f7129c598f6efd38657	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0900000000-0f7129c598f6efd38657	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9600000000-5f2a3091897e5f0660cc	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0033433

FooDB ID

FDB011471

Phenol Explorer ID

Not Available

KNApSAcK ID

C00001367

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

390180

ChEBI ID

Not Available

PubChem Compound ID

441447

Kegg Compound ID

C08283

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. Servillo L, Giovane A, Casale R, Cautela D, D'Onofrio N, Balestrieri ML, Castaldo D: Homostachydrine (pipecolic acid betaine) as authentication marker of roasted blends of Coffea arabica and Coffea canephora (Robusta) beans. Food Chem. 2016 Aug 15;205:52-7. doi: 10.1016/j.foodchem.2016.02.154. Epub 2016 Mar 3.

2. Servillo L, Giovane A, Balestrieri ML, Ferrari G, Cautela D, Castaldo D: Occurrence of pipecolic acid and pipecolic acid betaine (homostachydrine) in Citrus genus plants. J Agric Food Chem. 2012 Jan 11;60(1):315-21. doi: 10.1021/jf204286r. Epub 2011 Dec 29.

3. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.

(S)-Homostachydrine (CHEM027641)

Structure for CHEM027641: (S)-Homostachydrine