ChemFOnt: Showing chemical card for Tenuazonic acid (CFc000017061)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:06:53 UTC

Chemfont ID

CFc000017061

Molecule Identification

Common Name

Tenuazonic acid

Definition

Tenuazonic acid is produced by Aspergillus species Causes rice leaf rot Tenuazonic acid is a mycotoxin. It is a toxic secondary metabolite, produced by Alternaria (e. g. Alternaria alternata or Alternaria tenuis) and Phoma species. It inhibits the protein synthesis machinery

Structure

MOL SDF PDB SMILES InChI

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 Weight

197.231

Monoisotopic Molecular Weight

197.105193351

IUPAC Name

3-acetyl-5-(butan-2-yl)-4-hydroxy-2,5-dihydro-1H-pyrrol-2-one

Traditional Name

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

CAS Registry Number

610-88-8

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

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0036074)
Cytoplasm (HMDB: HMDB0036074)

Source

Exogenous

Exogenous (HMDB: HMDB0036074)

Food

Food (HMDB: HMDB0036074)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0036074)

Physical Properties

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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon