Andrastin A

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 Search

SMILES

COC(=O)[C@@]12C(=O)C(C)C(=O)[C@]1(C)C(C)=C[C@@H]3[C@]2(C)CC[C@@H]4C(C)(C)[C@H](CC[C@@]34C=O)OC(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

Primary Target	Pharmacology	Condition	Potency
Protein farnesyltransferase 13 Target ID: CHEMBL2094108 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8682716	Inhibitor 8504		24.9 µM [IC50]
P-glycoprotein 1 54 Target ID: CHEMBL4302 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9531989	Inhibitor 8504

PubMed

Title	Date	PubMed
Tyrosine Induced Metabolome Alterations of Penicillium roqueforti and Quantitation of Secondary Key Metabolites in Blue-Mold Cheese.	2019-08-07	31298534
The developmental regulator Pcz1 affects the production of secondary metabolites in the filamentous fungus Penicillium roqueforti.	2018-01-05	29853169
Inflammation-associated gene expression in RAW 264.7 macrophages induced by toxins from fungi common on damp building materials.	2017-09	28535995
Silencing of a second dimethylallyltryptophan synthase of Penicillium roqueforti reveals a novel clavine alkaloid gene cluster.	2017-08	28620689
Enniatin B and beauvericin are common in Danish cereals and show high hepatotoxicity on a high-content imaging platform.	2017-05	27628925
Role of sfk1 Gene in the Filamentous Fungus Penicillium roqueforti.	2017	29270163
The Biosynthetic Gene Cluster for Andrastin A in Penicillium roqueforti.	2017	28529508
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.	2016-12	27707355
Cytochrome P450 for Citreohybridonol Synthesis: Oxidative Derivatization of the Andrastin Scaffold.	2016-01-15	26731665
Metabolomic and Transcriptomic Comparison of Solid-State and Submerged Fermentation of Penicillium expansum KACC 40815.	2016	26863302
Penicillium excelsum sp. nov from the Brazil Nut Tree Ecosystem in the Amazon Basin'.	2015	26717519
Fungal and bacterial metabolites associated with natural contamination of locally processed rice (Oryza sativa L.) in Nigeria.	2015	25767914
Occurrence of pre- and post-harvest mycotoxins and other secondary metabolites in Danish maize silage.	2014-07-31	25089350
Secondary metabolites from Penicillium corylophilum isolated from damp buildings.	2014-06-04	24891425
Mass spectrometry-based chemotaxonomic classification of Penicillium species (P. echinulatum, P. expansum, P. solitum, and P. oxalicum) and its correlation with antioxidant activity.	2012-09	22732319
Atlantinone A, a Meroterpenoid Produced by Penicillium ribeum and Several Cheese Associated Penicillium Species.	2012-02-23	24957375
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.	2011-06	20639229
In vitro cytotoxicity of fungi spoiling maize silage.	2011-01	20837087
Multi-mycotoxin analysis of maize silage by LC-MS/MS.	2010-05	20213172
Proteolytic activity, mycotoxins and andrastin A in Penicillium roqueforti strains isolated from Cabrales, Valdeón and Bejes-Tresviso local varieties of blue-veined cheeses.	2009-11-30	19837474
Genetic variation among Penicillium crustosum isolates from arctic and other ecological niches.	2007-08	17345131
Mycotoxins and other secondary metabolites produced in vitro by Penicillium paneum Frisvad and Penicillium roqueforti Thom isolated from baled grass silage in Ireland.	2006-11-29	17117820
Comparison of secondary metabolite production by Penicillium crustosum strains, isolated from Arctic and other various ecological niches.	2005-06-01	16329929
Andrastins A-C, new protein farnesyltransferase inhibitors produced by Penicillium sp. FO-3929. I. Producing strain, fermentation, isolation, and biological activities.	1996-05	8682716

Substance Class	Chemical Created by `admin` on `Tue Apr 01 19:50:05 GMT 2025` Edited by `admin` on `Tue Apr 01 19:50:05 GMT 2025`
Record UNII	VL8DJU4GFD
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

Andrastin A

Common Name

English

NSC-697452

Preferred 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

Code System Code Type Description

EPA CompTox

DTXSID70938482