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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 of ASPERLIN

SMILES

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

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

Unknown
139594
PubMed

PubMed

TitleDatePubMed
Biological properties of a new antibiotic, U-13,933.
1965
Isolation and characterization of a new antibiotic, U-13,933.
1965
Substance Class Chemical
Created
by admin
on Fri Dec 15 17:05:24 GMT 2023
Edited
by admin
on Fri Dec 15 17:05:24 GMT 2023
Record UNII
8KOW0SA4L3
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ASPERLIN
USAN  
USAN  
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
NSC-93158
Code 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
Created by admin on Fri Dec 15 17:05:24 GMT 2023 , Edited by admin on Fri Dec 15 17:05:24 GMT 2023
Code System Code Type Description
NSC
93158
Created by admin on Fri Dec 15 17:05:24 GMT 2023 , Edited by admin on Fri Dec 15 17:05:24 GMT 2023
PRIMARY
MESH
C560220
Created by admin on Fri Dec 15 17:05:24 GMT 2023 , Edited by admin on Fri Dec 15 17:05:24 GMT 2023
PRIMARY
ChEMBL
CHEMBL2103782
Created by admin on Fri Dec 15 17:05:24 GMT 2023 , Edited by admin on Fri Dec 15 17:05:24 GMT 2023
PRIMARY
CAS
30387-51-0
Created by admin on Fri Dec 15 17:05:24 GMT 2023 , Edited by admin on Fri Dec 15 17:05:24 GMT 2023
PRIMARY
NCI_THESAURUS
C90674
Created by admin on Fri Dec 15 17:05:24 GMT 2023 , Edited by admin on Fri Dec 15 17:05:24 GMT 2023
PRIMARY
EPA CompTox
DTXSID501037425
Created by admin on Fri Dec 15 17:05:24 GMT 2023 , Edited by admin on Fri Dec 15 17:05:24 GMT 2023
PRIMARY
FDA UNII
8KOW0SA4L3
Created by admin on Fri Dec 15 17:05:24 GMT 2023 , Edited by admin on Fri Dec 15 17:05:24 GMT 2023
PRIMARY
PUBCHEM
9859172
Created by admin on Fri Dec 15 17:05:24 GMT 2023 , Edited by admin on Fri Dec 15 17:05:24 GMT 2023
PRIMARY
NIH
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