ContaminantDB: L-Gizzerosine

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

Record Information

Version

1.0

Creation Date

2016-05-26 03:26:08 UTC

Update Date

2016-11-09 01:20:44 UTC

Accession Number

CHEM032493

Identification

Common Name

L-Gizzerosine

Class

Small Molecule

Description

L-Gizzerosine is isolated from mackerel meal. L-Gizzerosine is produced as a contaminant during fish meal manufacturing by reaction between histidine and protein in the fish meat. Causes gizzard erosion ("black vomit") in chicks.

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-amino-9-(4-Imidazolyl)-7-azanonanoic acid	HMDB
Gizzerosine	HMDB
N6-(2-(1H-Imidazol-4-yl)ethyl)-L-lysine	HMDB
2-Amino-6-{[2-(1H-imidazol-5-yl)ethyl]amino}hexanoate	Generator

Chemical Formula

C₁₁H₂₀N₄O₂

Average Molecular Mass

240.302 g/mol

Monoisotopic Mass

240.159 g/mol

CAS Registry Number

89238-78-8

IUPAC Name

2-amino-6-{[2-(1H-imidazol-5-yl)ethyl]amino}hexanoic acid

Traditional Name

2-amino-6-{[2-(3H-imidazol-4-yl)ethyl]amino}hexanoic acid

SMILES

NC(CCCCNCCC1=CN=CN1)C(O)=O

InChI Identifier

InChI=1S/C11H20N4O2/c12-10(11(16)17)3-1-2-5-13-6-4-9-7-14-8-15-9/h7-8,10,13H,1-6,12H2,(H,14,15)(H,16,17)

InChI Key

LFNFNJYYTXESHV-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids

Alternative Parents

Substituents

Alpha-amino acid
Imidazolyl carboxylic acid derivative
Medium-chain fatty acid
Amino fatty acid
Heterocyclic fatty acid
Aralkylamine
Fatty acyl
Fatty acid
Azole
Imidazole
Heteroaromatic compound
Amino acid
Carboxylic acid
Secondary aliphatic amine
Azacycle
Monocarboxylic acid or derivatives
Secondary amine
Organoheterocyclic compound
Primary aliphatic amine
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Amine
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Primary amine
Organopnictogen compound
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

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	2.08 g/L	ALOGPS
logP	-2.2	ALOGPS
logP	-3.3	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	2.68	ChemAxon
pKa (Strongest Basic)	10.2	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	104.03 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	64.89 m³·mol⁻¹	ChemAxon
Polarizability	26.87 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	splash10-008d-9500000000-006ba1f557b7a3656e2a	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0002-4900000000-a37fb3537f0b9595a115	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	splash10-006w-2980000000-16c895e55be26c5cb917	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-8910000000-8a4cdcda3c906353ed23	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000t-9100000000-f2e4e0bd3c9b26b0ac21	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0290000000-a6cfe2c0b6ce8b6ad9dc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00ds-4980000000-7a0670266de9906a0a5f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0fft-9300000000-9f6e0f1cb9f001421484	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0090000000-2953c2a18f55f838dfe4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-1890000000-cd12d6e99f9485c8d3ad	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9300000000-f530830df96b48e3d647	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0190000000-151b3ffe1e5ce4ce7056	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001j-9220000000-dd127995904f4d3ddcee	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000t-9100000000-916452e3944be8bd5147	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
1D NMR	13C 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

HMDB0039160

FooDB ID

FDB018684

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

8552449

ChEBI ID

169532

PubChem Compound ID

10377006

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

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

L-Gizzerosine (CHEM032493)

Structure for CHEM032493: L-Gizzerosine