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27689

Sigma-Aldrich

Concanamycin A

from Streptomyces sp., ≥80% (HPLC)

Synonym(s):

Folimycin

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About This Item

Empirical Formula (Hill Notation):
C46H75NO14
CAS Number:
80890-47-7
Molecular Weight:
866.09
Beilstein/REAXYS Number:
3560277
MDL number:
MFCD00210037
UNSPSC Code:
12352200
PubChem Substance ID:
329753012
NACRES:
NA.25

biological source

Streptomyces sp.

Quality Level

100

assay

≥80% (HPLC)

form

solid

antibiotic activity spectrum

viruses

mode of action

enzyme | inhibits

storage temp.

−20°C

SMILES string

CCC1C(O)C(C)C\C(C)=C\C=C\C(OC)C(OC(=O)\C(OC)=C\C(C)=C\C(C)C1O)C(C)C(O)C(C)[C@]2(O)C[C@@H](O[C@H]3C[C@@H](O)[C@H](OC(N)=O)[C@@H](C)O3)[C@H](C)C(O2)\C=C\C

InChI

1S/C46H75NO14/c1-13-16-34-28(7)37(58-38-22-33(48)43(31(10)57-38)60-45(47)53)23-46(54,61-34)30(9)41(51)29(8)42-35(55-11)18-15-17-24(3)19-26(5)39(49)32(14-2)40(50)27(6)20-25(4)21-36(56-12)44(52)59-42/h13,15-18,20-21,26-35,37-43,48-51,54H,14,19,22-23H2,1-12H3,(H2,47,53)/b16-13+,18-15+,24-17+,25-20+,36-21-/t26?,27?,28-,29?,30?,31-,32?,33-,34?,35?,37-,38+,39?,40?,41?,42?,43-,46+/m1/s1

InChI key

DJZCTUVALDDONK-LWLXYWDNSA-N

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General description

Chemical structure: macrolide

Application

Concanamycin A has been used as an inhibitor of the perforin pathway.[1]

Other Notes

Characterization of concanamycins A, B and C;[2] Selective inhibitor of the vacuolar proton-ATPase.[3][4][5]

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 1 Inhalation - Acute Tox. 2 Dermal - Acute Tox. 2 Oral - Eye Irrit. 2

Storage Class

6.1B - Non-combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
BCCG2615
BCCF5240
BCCB6236
BCBV8057
BCBZ4846

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Cytotoxic mechanisms in different forms of T-cell-mediated drug allergies
P. C. Kuechler
Allergy (2004)
Concanamycin A, the specific inhibitor of V-ATPases, binds to the V(o) subunit c.
Huss M
The Journal of Biological Chemistry, 277(43), 40544-40548 (2002)
R Guinea et al.
FEBS letters, 349(3), 327-330 (1994-08-08)
The selective inhibitor of the vacuolar proton-ATPase, concanamycin A, powerfully blocks influenza virus entry into cells, if present during the initial times of virus infection. Attachment of virus particles to cells is not prevented by concanamycin A, rather the exit
H. Kinashi et al.
The Journal of Antibiotics, 38, 1333-1333 (1984)
Wucheng Tao et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 33(9), 3738-3743 (2013-03-01)
Ambient GABA in the brain tonically activates extrasynaptic GABA(A) receptors, and activity-dependent changes in ambient GABA concentration can also activate GABA(B) receptors. To investigate an interaction between postsynaptic GABA(B) and GABA(A) receptors, we recorded GABA(A) currents elicited by exogenous GABA
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