ContaminantDB: Tenuazonic acid

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

Record Information

Version

1.0

Creation Date

2014-08-29 04:56:30 UTC

Update Date

2026-05-20 22:47:58 UTC

Accession Number

CHEM003006

Identification

Common Name

Tenuazonic acid

Class

Small Molecule

Description

Tenuazonic acid is a toxic secondary metabolite, produced by Alternaria (e. g. Alternaria alternata or Alternaria tenuis) and Phoma species. It inhibits the protein synthesis machinery. Tenuazonic acid belongs to the family of Beta-Amino Ketones. These are organic compounds containing a carboxylic acid, and an amine group attached to the C2 carbon atom.

Contaminant Sources

FooDB Chemicals
T3DB toxins

Contaminant Type

Food Toxin
Fungal Toxin
Metabolite
Mycotoxin
Natural Compound
Organic Compound
PFAS

Chemical Structure

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

Synonyms

Value	Source
Tenuazonate	Generator
Acid, tenuazonic	MeSH
3-Acetyl-1,5-dihydro-4-hydroxy-5-(1-methylpropyl)-2H-pyrrol-2-one, 9ci	HMDB
3-Acetyl-5-sec-butyl-4-hydroxy-L-3-pyrrolin-2-one	HMDB
3-Acetyl-5-sec-butyl-pyrrole-2,4-diol	HMDB
3-Acetyl-5-sec-butyltetramic acid	HMDB
L-Tenuazonic acid	HMDB
Vivotoxin	HMDB
Tenuazonic acid	MeSH

Chemical Formula

C₁₀H₁₅NO₃

Average Molecular Mass

197.231 g/mol

Monoisotopic Mass

197.105 g/mol

CAS Registry Number

610-88-8

IUPAC Name

Not Available

Traditional Name

3-acetyl-4-hydroxy-5-(sec-butyl)-1,5-dihydropyrrol-2-one

SMILES

CCC(C)C1NC(=O)C(C(C)=O)=C1O

InChI Identifier

InChI=1S/C10H15NO3/c1-4-5(2)8-9(13)7(6(3)12)10(14)11-8/h5,8,13H,4H2,1-3H3,(H,11,14)

InChI Key

CEIZFXOZIQNICU-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as pyrrolines. Pyrrolines are compounds containing a pyrroline ring, which is a five-member unsaturated aliphatic ring with one nitrogen atom and four carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrrolines

Sub Class

Not Available

Direct Parent

Pyrrolines

Alternative Parents

Substituents

Pyrroline
Vinylogous acid
Carboxamide group
Ketone
Lactam
Secondary carboxylic acid amide
Carboxylic acid derivative
Enol
Azacycle
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Organic oxide
Hydrocarbon derivative
Organic nitrogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular

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

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	74 - 75.5°C
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	7.6 g/L	ALOGPS
logP	0.17	ALOGPS
logP	0.57	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	2.81	ChemAxon
pKa (Strongest Basic)	-0.55	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.4 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	52.73 m³·mol⁻¹	ChemAxon
Polarizability	20.61 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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	splash10-0006-9800000000-bcfb00cf6a866cab84f3	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0ffx-9220000000-3efe8522a8334eb2c562	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
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-19a6160a2f4eb732a5c6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0900000000-cb450a2563e6af57c58b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-03di-0900000000-b84d2936dae91e688ba7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0900000000-c05c5e4cffa5cbca5423	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000w-2900000000-347b74f895c5fbe86394	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-066r-9100000000-9235d19135d7b87978cf	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0f6t-0900000000-e4443634dd422a7ba52c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-2900000000-896a08a45cd2007229ce	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000x-9100000000-5051d66e608a659ec7f3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-dc55dda2e38219c36c8f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0900000000-f949413f6412b576dcf8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9300000000-1bb6bae63d8eac08d4e5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0900000000-cc94bcc041f6d746620e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0005-2900000000-04182e6f71ae7ad3c846	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9100000000-d840225406cdc8dbb01a	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)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Tenuazonic acid is a toxic secondary metabolite, produced by Alternaria (e. g. Alternaria alternata or Alternaria tenuis) and Phoma species.

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

HMDB0036074

FooDB ID

FDB014906

Phenol Explorer ID

Not Available

KNApSAcK ID

C00001554

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Tenuazonic acid

Chemspider ID

10633644

ChEBI ID

Not Available

PubChem Compound ID

54678599

Kegg Compound ID

C08511

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.

Tenuazonic acid (CHEM003006)

Structure for CHEM003006: Tenuazonic acid