ASPERLIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C10H12O5
Molecular Weight	212.1993
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@H]1O[C@@H]1[C@@H]2OC(=O)C=C[C@@H]2OC(C)=O

InChI

InChIKey=SPKNARKFCOPTSY-XWPZMVOTSA-N

InChI=1S/C10H12O5/c1-5-9(13-5)10-7(14-6(2)11)3-4-8(12)15-10/h3-5,7,9-10H,1-2H3/t5-,7+,9+,10-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C10H12O5
Molecular Weight	212.1993
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/29135917 | https://www.ncbi.nlm.nih.gov/pubmed/21600879

Asperlin (also known as U-13,933), a fungal natural product that was isolated from marine-derived fungus Aspergillus sp. SF-5044 and exhibits antifungal and anti-inflammatory properties in vitro. Experiments in vivo have shown that this compound can prevent atherosclerosis through suppressing inflammation rather than ameliorating dyslipidemia. In addition, asperlin can be developed as a potential anti-cancer therapeutics. It shows anti-cancer properties through ROS generation and ATM pathway in human cervical carcinoma cells.

Originator

Approval Year

PubMed

Title	Date	PubMed
Biological properties of a new antibiotic, U-13,933.	1965	5883501
Isolation and characterization of a new antibiotic, U-13,933.	1965	5883500

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:40:12 GMT 2025` Edited by `admin` on `Mon Mar 31 18:40:12 GMT 2025`
Record UNII	8KOW0SA4L3
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NSC-93158

Preferred Name

English

ASPERLIN

Official Name

English

U 13,933

Code

English

ASPERLIN [USAN]

Common Name

English

U-13933

Code

English

U 13933

Code

English

U-13,933

Code

English

((2R,3S)-2-((2S,3R)-3-METHYLOXIRAN-2-YL)-6-OXO-2,3-DIHYDROPYRAN-3-YL) ACETATE

Systematic Name

English

2H-PYRAN-2-ONE, 5-(ACETYLOXY)-5,6-DIHYDRO-6-(3-METHYLOXIRANYL)-

Systematic Name

English

IBIOTIC PRODUCED BY ASPERGILLUS NIDULANS. (1) 2H-PYRAN-2-ONE, 5-(ACETYLOXY)-5,6-DIHYDRO-6-(3-METHYLOXIRANYL)-

Common Name

English

6,7-EPOXY-4,5-DIHYDROXY-2-OCTENOIC ACID .DELTA.-LACTONE ACETATE

Common Name

English

6-(1,2-Epoxypropyl)-5,6-dihydro-5-hydroxy-2H-pyran-2-one acetate

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C258