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Merck
CN

SML2385

Andrastin A

≥95% (HPLC)

Synonym(s):

(3β,5β,8α,9β,10α,13α)-3β-(acetyloxy)-4,4,8,12,16-pentamethyl-15,17,19-trioxoandrost-11-ene-14-carboxylic acid methyl ester

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About This Item

Empirical Formula (Hill Notation):
C28H38O7
CAS Number:
174232-42-9
Molecular Weight:
486.60
UNSPSC Code:
12352200
MDL number:
MFCD28898503
NACRES:
NA.21

Key Documents

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SMILES string

O(C1C(C2[C@@]([C@@H]3C(C4([C@](C(=C3)C)(C(=O)C(C4=O)C)C)C(=O)OC)(CC2)C)(CC1)C=O)(C)C)C(=O)C

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?/m0/s1

InChI key

GRBXNADBNJGZRK-BCMOVVIDSA-N

assay

≥95% (HPLC)

form

powder

color

white to beige

storage temp.

−20°C

Related Categories

Biochem/physiol Actions

Andrastin A is a meroterpenoid protein farnesyltransferase inhibitor with anticancer activity. It has been shown to inhibit the farnesyltransferase activity of the oncogenic Ras proteins and inhibit the efflux of anticancer drugs from multidrug-resistant cancer cells.
Farnesyltransferase inhibitor with anticancer activity; mycotoxin

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000055821
0000044450

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Juan F Rojas-Aedo et al.
Frontiers in microbiology, 8, 813-813 (2017-05-23)
Penicillium roqueforti is a filamentous fungus involved in the ripening of several kinds of blue cheeses. In addition, this fungus produces several secondary metabolites, including the meroterpenoid compound andrastin A, a promising antitumoral compound. However, to date the genomic cluster
Kristian Fog Nielsen et al.
Journal of agricultural and food chemistry, 53(8), 2908-2913 (2005-04-14)
This is the first finding of andrastins in blue cheese as well as any other sample type. Here, they were produced by the secondary starter culture Penicillium roqueforti. After purification by normal-phase chromatography followed by combined reverse-phase ion-exchange chromatography, the
Mytre Koul et al.
Anti-cancer drugs, 28(1), 11-30 (2016-08-24)
Secondary metabolites from fungal endophytes have become an interesting, attractive, and alternative source for novel pharmaceuticals. Several novel compounds with diversified chemical structures have been isolated from endophytic fungi. The genus Penicillium has been exploited worldwide for its biosynthetic potential

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