PENICILLIC ACID

Details

Stereochemistry	ACHIRAL
Molecular Formula	C8H10O4
Molecular Weight	170.1626
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CO\C(=C\C(O)=O)C(=O)C(C)=C

InChI

InChIKey=VOUGEZYPVGAPBB-GQCTYLIASA-N

InChI=1S/C8H10O4/c1-5(2)8(11)6(12-3)4-7(9)10/h4H,1H2,2-3H3,(H,9,10)/b6-4+

HIDE SMILES / InChI

Molecular Formula	C8H10O4
Molecular Weight	170.1626
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3100345 | https://www.ncbi.nlm.nih.gov/pubmed/580698 | https://www.ncbi.nlm.nih.gov/pubmed/6472435

Penicillic acid (PA) is a polyketide mycotoxin produced by several species of Aspergillus and Penicillium species showed antibacterial activity against various plant pathogenic bacteria and can be as a lead molecule for the development of synthetic agrochemicals to control plant bacterial diseases. In addition, PA induces single-strand DNA breaks and inhibits DNA synthesis, demonstrating mutagenic and cytotoxic effects. Penicillic acid irreversibly inhibits GDP-mannose dehydrogenase (DMG), an alginate synthesis enzyme, interrupting the committed step in alginate biosynthesis.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
GDP-mannose 6-dehydrogenase 1 Target ID: P11759 Gene ID: 879004.0 Gene Symbol: algD Target Organism: Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG\|\|\|12228) Sources: https://www.ncbi.nlm.nih.gov/pubmed/16111644	Inhibitor 8297
Glutathione S-transferase P 1 Target ID: P04906 Gene ID: 24426.0 Gene Symbol: Gstp1 Target Organism: Rattus norvegicus (Rat) Sources: https://www.ncbi.nlm.nih.gov/pubmed/6472435	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Acute toxicity of penicillic acid and rubratoxin B in dogs.	1977	580698
Interaction of the mycotoxin penicillic acid with glutathione and rat liver glutathione S-transferases.	1984 Jun 30	6472435
Toxicity of penicillic acid for rat alveolar macrophages in vitro.	1986 Dec	2430790
Inactivation of GDP-mannose dehydrogenase from Pseudomonas aeruginosa by penicillic acid identifies a critical active site loop.	2005 Sep 15	16111644

Patents

Sample Use Guides

In Vivo Use Guide

toxicity of penicillic acid in dogs: 20 mg/kg

Route of Administration: Oral

In Vitro Use Guide

Penicillic acid is toxic to rat alveolar macrophages in vitro. The cytotoxicity of penicillic acid was studied in rat alveolar macrophages (AM) in vitro. The effects of penicillic acid on membrane integrity were studied by measuring cell volume changes and 51Cr release. There was significant 51Cr release after 2 hr exposure to 1.0 mM penicillic acid, but not after 1 hr exposure. There was a significant decrease in adenosine triphosphate (ATP) in cell cultures exposed to 1.0 mM penicillic acid for 4 hr. Inhibition of the incorporation of [3H]leucine into protein was both dose- and time-dependent and protein synthesis was inhibited significantly after 2 hr exposure to greater than or equal to 0.1 mM penicillic acid

Substance Class	Chemical Created by `admin` on `Fri Dec 15 18:30:29 GMT 2023` Edited by `admin` on `Fri Dec 15 18:30:29 GMT 2023`
Record UNII	ONL14K3AFD
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PENICILLIC ACID

Systematic Name

English

PENICILLIC ACID [IARC]

Common Name

English

PENICILLIC ACID [MI]

Common Name

English

3-METHOXY-5-METHYL-4-OXO-2,5-HEXADIENOIC ACID

Systematic Name

English

PENICILLIC ACID [HSDB]

Common Name

English

Code System Code Type Description

EPA CompTox

DTXSID1074830