2-(2-{[10-(6-amino-2-{6-amino-2-[2-(2-{[7,34-bis(4-aminobutyl)-37-{2-[2-(2-{[10-(4-aminobutyl)-22-(3-carboxy-2-{2-[3-carboxy-2-(3-hydroxy-2-{2-[(5-oxopyrrolidin-2-yl)formamido]-3-phenylpropanamido}butanamido)propanamido]-3-methylbutanamido}propanamido)-7-(2-carboxyethyl)-13,19-bis(hydroxymethyl)-6,9,12,15,18,21-hexaoxo-16-(propan-2-yl)-1,2-dithia-5,8,11,14,17,20-hexaazacyclotricosan-4-yl]formamido}-3-(1H-indol-3-yl)propanamido)-3-hydroxypropanamido]-3-methylbutanamido}-25-benzyl-13-(3-carbamimidamidopropyl)-16,31-bis(carboxymethyl)-28-(2-methylpropyl)-6,9,12,15,18,21,24,27,30,33,36-undecaoxo-19-(propan-2-yl)-1,2-dithia-5,8,11,14,17,20,23,26,29,32,35-undecaazacyclooctatriacontan-4-yl]formamido}-4-(methylsulfanyl)butanamido)acetamido]hexanamido}hexanamido)-7-(3-carbamimidamidopropyl)-6,9-dioxo-1,2-dithia-5,8-diazacycloundecan-4-yl]formamido}-3-(4-hydroxyphenyl)propanamido)-4-carbamoylbutanoic acid

• ChemBase ID: 132146
• Molecular Formular: C179H274N50O55S7
• Molecular Mass: 4230.84786
• Monoisotopic Mass: 4227.82256012
• SMILES: CC(C)CC1C(=O)NC(C(=O)NCC(=O)NC(C(=O)NC(C(=O)NC(C(=O)NCC(=O)NC(C(=O)NC(CSSCC(C(=O)NC(C(=O)NC(C(=O)N1)CC(=O)O)CCCCN)NC(=O)C(C(C)C)NC(=O)C(CO)NC(=O)C(Cc1c[nH]c2c1cccc2)NC(=O)C1CSSCC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N1)CCC(=O)O)CCCCN)CO)C(C)C)CO)NC(=O)C(CC(=O)O)NC(=O)C(C(C)C)NC(=O)C(CC(=O)O)NC(=O)C(C(C)O)NC(=O)C(Cc1ccccc1)NC(=O)C1CCC(=O)N1)C(=O)NC(CCSC)C(=O)NCC(=O)NC(CCCCN)C(=O)NC(CCCCN)C(=O)NC1CSSCC(NC(=O)C(NC1=O)CCCNC(=N)N)C(=O)NC(Cc1ccc(cc1)O)C(=O)NC(CCC(=O)N)C(=O)O)CCCCN)CCCNC(=N)N)CC(=O)O)C(C)C)Cc1ccccc1
• Canonical SMILES: NCCCCC1NC(=O)C(CSSCC(NC(=O)C(CCCCN)NC(=O)CNC(=O)C(CCCNC(=N)N)NC(=O)C(NC(=O)C(NC(=O)CNC(=O)C(NC(=O)C(NC(=O)C(NC1=O)CC(=O)O)CC(C)C)Cc1ccccc1)C(C)C)CC(=O)O)C(=O)NC(C(=O)NCC(=O)NC(C(=O)NC(C(=O)NC1CSSCC(NC(=O)C(NC1=O)CCCNC(=N)N)C(=O)NC(C(=O)NC(C(=O)O)CCC(=O)N)Cc1ccc(cc1)O)CCCCN)CCCCN)CCSC)NC(=O)C(C(C)C)NC(=O)C(NC(=O)C(Cc1c[nH]c2c1cccc2)NC(=O)C1CSSCC(NC(=O)C(NC(=O)C(C(C)C)NC(=O)C(NC(=O)C(C(O)C)NC(=O)C(NC(=O)C2CCC(=O)N2)Cc2ccccc2)CC(=O)O)CC(=O)O)C(=O)NC(CO)C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N1)CCC(=O)O)CCCCN)CO)C(C)C)CO
• InChI: 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)
• InChIKey: VDNVVLOBNHIMQA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(2-{[10-(6-amino-2-{6-amino-2-[2-(2-{[7,34-bis(4-aminobutyl)-37-{2-[2-(2-{[10-(4-aminobutyl)-22-(3-carboxy-2-{2-[3-carboxy-2-(3-hydroxy-2-{2-[(5-oxopyrrolidin-2-yl)formamido]-3-phenylpropanamido}butanamido)propanamido]-3-methylbutanamido}propanamido)-7-(2-carboxyethyl)-13,19-bis(hydroxymethyl)-6,9,12,15,18,21-hexaoxo-16-(propan-2-yl)-1,2-dithia-5,8,11,14,17,20-hexaazacyclotricosan-4-yl]formamido}-3-(1H-indol-3-yl)propanamido)-3-hydroxypropanamido]-3-methylbutanamido}-25-benzyl-13-(3-carbamimidamidopropyl)-16,31-bis(carboxymethyl)-28-(2-methylpropyl)-6,9,12,15,18,21,24,27,30,33,36-undecaoxo-19-(propan-2-yl)-1,2-dithia-5,8,11,14,17,20,23,26,29,32,35-undecaazacyclooctatriacontan-4-yl]formamido}-4-(methylsulfanyl)butanamido)acetamido]hexanamido}hexanamido)-7-(3-carbamimidamidopropyl)-6,9-dioxo-1,2-dithia-5,8-diazacycloundecan-4-yl]formamido}-3-(4-hydroxyphenyl)propanamido)-4-carbamoylbutanoic acid
• IUPAC Traditional name: 2-(2-{[10-(6-amino-2-{6-amino-2-[2-(2-{[7,34-bis(4-aminobutyl)-37-{2-[2-(2-{[10-(4-aminobutyl)-22-(3-carboxy-2-{2-[3-carboxy-2-(3-hydroxy-2-{2-[(5-oxopyrrolidin-2-yl)formamido]-3-phenylpropanamido}butanamido)propanamido]-3-methylbutanamido}propanamido)-7-(2-carboxyethyl)-13,19-bis(hydroxymethyl)-16-isopropyl-6,9,12,15,18,21-hexaoxo-1,2-dithia-5,8,11,14,17,20-hexaazacyclotricosan-4-yl]formamido}-3-(1H-indol-3-yl)propanamido)-3-hydroxypropanamido]-3-methylbutanamido}-25-benzyl-13-(3-carbamimidamidopropyl)-16,31-bis(carboxymethyl)-19-isopropyl-28-(2-methylpropyl)-6,9,12,15,18,21,24,27,30,33,36-undecaoxo-1,2-dithia-5,8,11,14,17,20,23,26,29,32,35-undecaazacyclooctatriacontan-4-yl]formamido}-4-(methylsulfanyl)butanamido)acetamido]hexanamido}hexanamido)-7-(3-carbamimidamidopropyl)-6,9-dioxo-1,2-dithia-5,8-diazacycloundecan-4-yl]formamido}-3-(4-hydroxyphenyl)propanamido)-4-carbamoylbutanoic acid
• Synonyms: Iberiotoxin

Database IDs

• CAS Number: 129203-60-7
• MDL Number: MFCD00131365
• PubChem SID: 162226423; 24895960
• PubChem CID: 16132435

CALCULATED PROPERTIES

• H Acceptors: 66
• H Donor: 61
• LogD (pH = 5.5): -30.795197
• LogD (pH = 7.4): -37.315395
• Log P: -24.76212
• Molar Refractivity: 1068.783 cm^3
• Polarizability: 412.05682 Å^3
• Polar Surface Area: 1714.43 Å^2
• Rotatable Bonds: 98
• Lipinski's Rule of Five: false
• Acid pKa: 2.7470853

PROPERTIES

Physical Property

• Solubility: H2O: soluble1 mg/mL, clear, colorless

Safety Information

• European Hazard Symbols: Highly toxic (T+)
• UN Number: 3462
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2
• Risk Statements: 26/27/28
• Safety Statements: 28-36/37-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300-H310-H330
• GHS Precautionary statements: P260-P264-P280-P284-P301 + P310-P302 + P350
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 3462 6.1/PG 2
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... KCNMA1(3778)mouse ... KCNMA1(16531)rat ... KCNMA1(83731)

Product Information

• Purity: ≥85% (HPLC)
• Biological Source: from Buthus tamulus
• Empirical Formula (Hill Notation): C179H274N50O55S7

DETAILS

Sigma Aldrich - I2141

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

Sigma Aldrich - 56718

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.