U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry EPIMERIC
Molecular Formula C28H38O7
Molecular Weight 486.5971
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Andrastin A

SMILES

[H][C@]12CC[C@@]3(C)[C@@]([H])(C=C(C)[C@@]4(C)C(=O)C(C)C(=O)[C@@]34C(=O)OC)[C@@]1(CC[C@H](OC(C)=O)C2(C)C)C=O

InChI

InChIKey=GRBXNADBNJGZRK-GJEDHNSHSA-N
InChI=1S/C28H38O7/c1-15-13-19-25(6,28(23(33)34-8)22(32)16(2)21(31)26(15,28)7)11-9-18-24(4,5)20(35-17(3)30)10-12-27(18,19)14-29/h13-14,16,18-20H,9-12H2,1-8H3/t16?,18-,19-,20+,25+,26+,27+,28-/m1/s1

HIDE SMILES / InChI

Molecular Formula C28H38O7
Molecular Weight 486.5971
Charge 0
Count
Stereochemistry EPIMERIC
Additional Stereochemistry No
Defined Stereocenters 7 / 8
E/Z Centers 0
Optical Activity UNSPECIFIED

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
24.9 µM [IC50]
PubMed

PubMed

TitleDatePubMed
Andrastins A-C, new protein farnesyltransferase inhibitors produced by Penicillium sp. FO-3929. I. Producing strain, fermentation, isolation, and biological activities.
1996 May
Comparison of secondary metabolite production by Penicillium crustosum strains, isolated from Arctic and other various ecological niches.
2005 Jun 1
Mycotoxins and other secondary metabolites produced in vitro by Penicillium paneum Frisvad and Penicillium roqueforti Thom isolated from baled grass silage in Ireland.
2006 Nov 29
Genetic variation among Penicillium crustosum isolates from arctic and other ecological niches.
2007 Aug
Proteolytic activity, mycotoxins and andrastin A in Penicillium roqueforti strains isolated from Cabrales, Valdeón and Bejes-Tresviso local varieties of blue-veined cheeses.
2009 Nov 30
Multi-mycotoxin analysis of maize silage by LC-MS/MS.
2010 May
In vitro cytotoxicity of fungi spoiling maize silage.
2011 Jan
Penicillium araracuarense sp. nov., Penicillium elleniae sp. nov., Penicillium penarojense sp. nov., Penicillium vanderhammenii sp. nov. and Penicillium wotroi sp. nov., isolated from leaf litter.
2011 Jun
Atlantinone A, a Meroterpenoid Produced by Penicillium ribeum and Several Cheese Associated Penicillium Species.
2012 Feb 23
Mass spectrometry-based chemotaxonomic classification of Penicillium species (P. echinulatum, P. expansum, P. solitum, and P. oxalicum) and its correlation with antioxidant activity.
2012 Sep
Occurrence of pre- and post-harvest mycotoxins and other secondary metabolites in Danish maize silage.
2014 Jul 31
Secondary metabolites from Penicillium corylophilum isolated from damp buildings.
2014 Jul-Aug
Penicillium excelsum sp. nov from the Brazil Nut Tree Ecosystem in the Amazon Basin'.
2015
Fungal and bacterial metabolites associated with natural contamination of locally processed rice (Oryza sativa L.) in Nigeria.
2015
Metabolomic and Transcriptomic Comparison of Solid-State and Submerged Fermentation of Penicillium expansum KACC 40815.
2016
Validation and application of a liquid chromatography-tandem mass spectrometry based method for the assessment of the co-occurrence of mycotoxins in maize silages from dairy farms in NW Spain.
2016 Dec
Cytochrome P450 for Citreohybridonol Synthesis: Oxidative Derivatization of the Andrastin Scaffold.
2016 Jan 15
Role of sfk1 Gene in the Filamentous Fungus Penicillium roqueforti.
2017
The Biosynthetic Gene Cluster for Andrastin A in Penicillium roqueforti.
2017
Silencing of a second dimethylallyltryptophan synthase of Penicillium roqueforti reveals a novel clavine alkaloid gene cluster.
2017 Aug
Enniatin B and beauvericin are common in Danish cereals and show high hepatotoxicity on a high-content imaging platform.
2017 May
Inflammation-associated gene expression in RAW 264.7 macrophages induced by toxins from fungi common on damp building materials.
2017 Sep
The developmental regulator Pcz1 affects the production of secondary metabolites in the filamentous fungus Penicillium roqueforti.
2018 Jul-Aug
Tyrosine Induced Metabolome Alterations of Penicillium roqueforti and Quantitation of Secondary Key Metabolites in Blue-Mold Cheese.
2019 Aug 7
Substance Class Chemical
Created
by admin
on Sat Dec 16 12:49:31 GMT 2023
Edited
by admin
on Sat Dec 16 12:49:31 GMT 2023
Record UNII
VL8DJU4GFD
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
Andrastin A
Common Name English
Andrastin A, Aspergillus fumigatus
Common Name English
METHYL 3-(ACETYLOXY)-4,4,8,12,16-PENTAMETHYL-15,17,19-TRIOXOANDROST-11-ENE-14-CARBOXYLATE
Systematic Name English
NSC-697452
Code English
Code System Code Type Description
EPA CompTox
DTXSID70938482
Created by admin on Sat Dec 16 12:49:31 GMT 2023 , Edited by admin on Sat Dec 16 12:49:31 GMT 2023
PRIMARY
CAS
174232-42-9
Created by admin on Sat Dec 16 12:49:31 GMT 2023 , Edited by admin on Sat Dec 16 12:49:31 GMT 2023
PRIMARY
NSC
697452
Created by admin on Sat Dec 16 12:49:31 GMT 2023 , Edited by admin on Sat Dec 16 12:49:31 GMT 2023
PRIMARY
PUBCHEM
496693
Created by admin on Sat Dec 16 12:49:31 GMT 2023 , Edited by admin on Sat Dec 16 12:49:31 GMT 2023
PRIMARY
WIKIPEDIA
Andrastin A
Created by admin on Sat Dec 16 12:49:31 GMT 2023 , Edited by admin on Sat Dec 16 12:49:31 GMT 2023
PRIMARY
FDA UNII
VL8DJU4GFD
Created by admin on Sat Dec 16 12:49:31 GMT 2023 , Edited by admin on Sat Dec 16 12:49:31 GMT 2023
PRIMARY