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I2141

Sigma-Aldrich

Iberiotoxin

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About This Item

Empirical Formula (Hill Notation):
C179H274N50O55S7
CAS Number:
129203-60-7
Molecular Weight:
4230.85
MDL number:
MFCD00131365
UNSPSC Code:
12352200
PubChem Substance ID:
24895960

assay

≥85% (HPLC)

solubility

H2O: 1 mg/mL, clear, colorless

storage temp.

−20°C

SMILES string

CSCCC(NC(=O)C1CSSCC(NC(=O)C(NC(=O)C(CO)NC(=O)C(Cc2c[nH]c3ccccc23)NC(=O)C4CSSCC(NC(=O)C(CC(O)=O)NC(=O)C(NC(=O)C(CC(O)=O)NC(=O)C(NC(=O)C(Cc5ccccc5)NC(=O)C6CCC(=O)N6)C(C)O)C(C)C)C(=O)NC(CO)C(=O)NC(C(C)C)C(=O)NC(CO)C(=O)NC(CCCCN)C(=O)NC(CCC(O)=O)C(=O)N4)C(C)C)C(=O)NC(CCCCN)C(=O)NC(CC(O)=O)C(=O)NC(CC(C)C)C(=O)NC(Cc7ccccc7)C(=O)NCC(=O)NC(C(C)C)C(=O)NC(CC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CCCCN)C(=O)N1)C(=O)NCC(=O)NC(CCCCN)C(=O)NC(CCCCN)C(=O)NC8CSSCC(NC(=O)C(CCCNC(N)=N)NC8=O)C(=O)NC(Cc9ccc(O)cc9)C(=O)NC(CCC(N)=O)C(O)=O

InChI

1S/C179H274N50O55S7/c1-87(2)65-111-155(261)208-112(66-93-33-15-13-16-34-93)146(252)195-77-133(239)225-139(88(3)4)172(278)213-117(71-136(244)245)158(264)199-100(44-31-62-190-178(186)187)144(250)193-75-131(237)198-102(40-22-27-58-181)148(254)219-124(167(273)205-109(56-64-285-12)145(251)194-76-132(238)197-101(39-21-26-57-180)147(253)200-105(43-25-30-61-184)151(257)220-123-81-286-288-83-125(221-152(258)106(203-166(123)272)45-32-63-191-179(188)189)169(275)210-113(68-95-46-48-97(234)49-47-95)156(262)206-110(177(283)284)50-53-129(185)235)82-287-291-86-128(168(274)202-104(42-24-29-60-183)150(256)212-116(70-135(242)243)159(265)207-111)224-175(281)142(91(9)10)228-164(270)121(79-231)216-157(263)115(69-96-74-192-99-38-20-19-37-98(96)99)211-170(276)126-84-289-290-85-127(171(277)217-122(80-232)165(271)227-141(90(7)8)174(280)218-120(78-230)163(269)201-103(41-23-28-59-182)149(255)204-108(154(260)222-126)52-55-134(240)241)223-160(266)118(72-137(246)247)214-173(279)140(89(5)6)226-162(268)119(73-138(248)249)215-176(282)143(92(11)233)229-161(267)114(67-94-35-17-14-18-36-94)209-153(259)107-51-54-130(236)196-107/h13-20,33-38,46-49,74,87-92,100-128,139-143,192,230-234H,21-32,39-45,50-73,75-86,180-184H2,1-12H3,(H2,185,235)(H,193,250)(H,194,251)(H,195,252)(H,196,236)(H,197,238)(H,198,237)(H,199,264)(H,200,253)(H,201,269)(H,202,274)(H,203,272)(H,204,255)(H,205,273)(H,206,262)(H,207,265)(H,208,261)(H,209,259)(H,210,275)(H,211,276)(H,212,256)(H,213,278)(H,214,279)(H,215,282)(H,216,263)(H,217,277)(H,218,280)(H,219,254)(H,220,257)(H,221,258)(H,222,260)(H,223,266)(H,224,281)(H,225,239)(H,226,268)(H,227,271)(H,228,270)(H,229,267)(H,240,241)(H,242,243)(H,244,245)(H,246,247)(H,248,249)(H,283,284)(H4,186,187,190)(H4,188,189,191)

InChI key

VDNVVLOBNHIMQA-UHFFFAOYSA-N

Gene Information

human ... KCNMA1(3778)
mouse ... KCNMA1(16531)
rat ... KCNMA1(83731)

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Amino Acid Sequence

pGlu-Phe-Thr-Asp-Val-Asp-Cys-Ser-Val-Ser-Lys-Glu-Cys-Trp-Ser-Val-Cys-Lys-Asp-Leu-Phe-Gly-Val-Asp-Arg-Gly-Lys-Cys-Met-Gly-Lys-Lys-Cys-Arg-Cys-Tyr-Gln [Disulfide Bridges: 7−28; 13−33; 17−35]

Biochem/physiol Actions

Selective and reversible inhibitor of high-conductance calcium-activated potassium channel.

Other Notes

Originally isolated from Heteropoda venatoria

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

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

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk_germany

WGK 3

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
119K8711
041K1355
068K8715
115K11081
075K14832

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Kenichi Goto et al.
Hypertension research : official journal of the Japanese Society of Hypertension, 35(8), 849-854 (2012-04-06)
This study was designed to determine whether a high-salt diet would alter endothelial function and, if so, the relative contributions of endothelium-derived hyperpolarizing factor (EDHF) and nitric oxide (NO) to any changes in vasomotor responses. Male Dahl salt-sensitive (DS) rats
Olav Schjørring et al.
The journal of sexual medicine, 9(7), 1789-1800 (2012-05-03)
Endothelium-derived relaxing factors such as nitric oxide (NO), prostanoids, and endothelium-derived hyperpolarizing factor (EDHF) are thought to play an important role in vasodilation of penile arteries. The present study investigated the mechanisms involved in flow- and acetylcholine-induced vasodilation in penile
Hui Ye et al.
Neurobiology of disease, 47(2), 225-236 (2012-04-27)
Spinal cord injury (SCI) causes neuronal death, demyelination of surviving axons, and altered ion channel functioning, resulting in impaired axonal conduction. The large-conductance, voltage and Ca(2+)-activated K(+) (BK or Maxi K(+)) channels contribute to the repolarization phase of action potentials.
Roland S Wu et al.
The Journal of general physiology, 141(1), 105-117 (2013-01-02)
Large-conductance voltage- and Ca(2+)-gated K(+) channels are negative-feedback regulators of excitability in many cell types. They are complexes of α subunits and of one of four types of modulatory β subunits. These have intracellular N- and C-terminal tails and two
Kristi A Kohlmeier et al.
Neuropharmacology, 66, 99-113 (2012-03-03)
Cholinergic neurons of the pontine laterodorsal tegmentum (LDT) are importantly involved in neurobiological mechanisms governing states of arousal such as sleep and wakefulness as well as other appetitive behaviors, such as drug-seeking. Accordingly, mechanisms controlling their excitability are important to
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