(4S)-4-{[(1R)-1-{[(1S)-1-{[(1S)-5-amino-1-{[(1S)-1-carbamoyl-2-(1H-imidazol-4-yl)ethyl]carbamoyl}pentyl]carbamoyl}-2-methylpropyl]carbamoyl}-2-sulfanylethyl]carbamoyl}-4-[(2R)-2-[(2S)-6-amino-2-[(2S)-2-{2-[(2S,3S)-2-[(2R)-2-[(2S)-6-amino-2-{2-[(2S)-2-[(2S)-2-{2-[(2S)-2-[(2S)-2-[(2S)-2-[(2R)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2R)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2R)-2-[(2S)-2-[(2S)-2-aminopropanamido]-3-phenylpropanamido]-3-sulfanylpropanamido]-3-carbamoylpropanamido]-4-methylpentanamido]-5-carbamimidamidopentanamido]-4-(methylsulfanyl)butanamido]-3-sulfanylpropanamido]-4-carbamoylbutanamido]-4-methylpentanamido]-3-hydroxypropanamido]-3-sulfanylpropanamido]-5-carbamimidamidopentanamido]-3-hydroxypropanamido]-4-methylpentanamido]acetamido}-4-methylpentanamido]-4-methylpentanamido]acetamido}hexanamido]-3-sulfanylpropanamido]-3-methylpentanamido]acetamido}-3-carboxypropanamido]hexanamido]-3-sulfanylpropanamido]butanoic acid

• ChemBase ID: 153925
• Molecular Formular: C142H243N45O39S7
• Molecular Mass: 3429.18192
• Monoisotopic Mass: 3426.64598018
• SMILES: CC[C@H](C)[C@@H](C(=O)NCC(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CS)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CS)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](Cc1c[nH]cn1)C(=O)N)NC(=O)[C@H](CS)NC(=O)[C@H](CCCCN)NC(=O)CNC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)CNC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CS)NC(=O)[C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(=O)N)NC(=O)[C@H](CS)NC(=O)[C@H](CCSC)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(=O)N)NC(=O)[C@H](CS)NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](C)N
• Canonical SMILES: NCCCC[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)NCC(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N)Cc1nc[nH]c1)CCCCN)C(C)C)CS)CCC(=O)O)CS)CCCCN)CC(=O)O)[C@H](CC)C)CS)NC(=O)CNC(=O)[C@@H](NC(=O)[C@@H](NC(=O)CNC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](N)C)Cc1ccccc1)CS)CC(=O)N)CC(C)C)CCCNC(=N)N)CCSC)CS)CCC(=O)N)CC(C)C)CO)CS)CCCNC(=N)N)CO)CC(C)C)CC(C)C)CC(C)C
• InChI: InChI=1S/C142H243N45O39S7/c1-17-75(14)112(139(225)159-59-108(194)163-95(55-110(197)198)130(216)164-80(32-22-25-42-144)121(207)180-98(62-227)135(221)168-85(37-39-109(195)196)123(209)183-102(66-231)137(223)186-111(74(12)13)140(226)170-81(33-23-26-43-145)119(205)171-87(113(149)199)53-78-56-154-68-160-78)187-138(224)103(67-232)182-117(203)79(31-21-24-41-143)161-106(192)57-157-115(201)88(47-69(2)3)173-125(211)90(49-71(6)7)162-107(193)58-158-116(202)89(48-70(4)5)174-131(217)96(60-188)178-120(206)83(35-28-45-156-142(152)153)166-133(219)100(64-229)185-132(218)97(61-189)179-127(213)92(51-73(10)11)175-122(208)84(36-38-104(147)190)167-134(220)99(63-228)181-124(210)86(40-46-233-16)169-118(204)82(34-27-44-155-141(150)151)165-126(212)91(50-72(8)9)176-129(215)94(54-105(148)191)177-136(222)101(65-230)184-128(214)93(172-114(200)76(15)146)52-77-29-19-18-20-30-77/h18-20,29-30,56,68-76,79-103,111-112,188-189,227-232H,17,21-28,31-55,57-67,143-146H2,1-16H3,(H2,147,190)(H2,148,191)(H2,149,199)(H,154,160)(H,157,201)(H,158,202)(H,159,225)(H,161,192)(H,162,193)(H,163,194)(H,164,216)(H,165,212)(H,166,219)(H,167,220)(H,168,221)(H,169,204)(H,170,226)(H,171,205)(H,172,200)(H,173,211)(H,174,217)(H,175,208)(H,176,215)(H,177,222)(H,178,206)(H,179,213)(H,180,207)(H,181,210)(H,182,203)(H,183,209)(H,184,214)(H,185,218)(H,186,223)(H,187,224)(H,195,196)(H,197,198)(H4,150,151,155)(H4,152,153,156)/t75-,76-,79-,80-,81-,82-,83-,84-,85-,86-,87-,88-,89-,90-,91-,92-,93-,94-,95-,96-,97-,98-,99-,100-,101-,102-,103-,111-,112-/m0/s1
• InChIKey: MXWDLLUGULWYIQ-BFRWRHKQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-{[(1R)-1-{[(1S)-1-{[(1S)-5-amino-1-{[(1S)-1-carbamoyl-2-(1H-imidazol-4-yl)ethyl]carbamoyl}pentyl]carbamoyl}-2-methylpropyl]carbamoyl}-2-sulfanylethyl]carbamoyl}-4-[(2R)-2-[(2S)-6-amino-2-[(2S)-2-{2-[(2S,3S)-2-[(2R)-2-[(2S)-6-amino-2-{2-[(2S)-2-[(2S)-2-{2-[(2S)-2-[(2S)-2-[(2S)-2-[(2R)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2R)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2R)-2-[(2S)-2-[(2S)-2-aminopropanamido]-3-phenylpropanamido]-3-sulfanylpropanamido]-3-carbamoylpropanamido]-4-methylpentanamido]-5-carbamimidamidopentanamido]-4-(methylsulfanyl)butanamido]-3-sulfanylpropanamido]-4-carbamoylbutanamido]-4-methylpentanamido]-3-hydroxypropanamido]-3-sulfanylpropanamido]-5-carbamimidamidopentanamido]-3-hydroxypropanamido]-4-methylpentanamido]acetamido}-4-methylpentanamido]-4-methylpentanamido]acetamido}hexanamido]-3-sulfanylpropanamido]-3-methylpentanamido]acetamido}-3-carboxypropanamido]hexanamido]-3-sulfanylpropanamido]butanoic acid
• IUPAC Traditional name: (4S)-4-{[(1R)-1-{[(1S)-1-{[(1S)-5-amino-1-{[(1S)-1-carbamoyl-2-(1H-imidazol-4-yl)ethyl]carbamoyl}pentyl]carbamoyl}-2-methylpropyl]carbamoyl}-2-sulfanylethyl]carbamoyl}-4-[(2R)-2-[(2S)-6-amino-2-[(2S)-2-{2-[(2S,3S)-2-[(2R)-2-[(2S)-6-amino-2-{2-[(2S)-2-[(2S)-2-{2-[(2S)-2-[(2S)-2-[(2S)-2-[(2R)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2R)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2R)-2-[(2S)-2-[(2S)-2-aminopropanamido]-3-phenylpropanamido]-3-sulfanylpropanamido]-3-carbamoylpropanamido]-4-methylpentanamido]-5-carbamimidamidopentanamido]-4-(methylsulfanyl)butanamido]-3-sulfanylpropanamido]-4-carbamoylbutanamido]-4-methylpentanamido]-3-hydroxypropanamido]-3-sulfanylpropanamido]-5-carbamimidamidopentanamido]-3-hydroxypropanamido]-4-methylpentanamido]acetamido}-4-methylpentanamido]-4-methylpentanamido]acetamido}hexanamido]-3-sulfanylpropanamido]-3-methylpentanamido]acetamido}-3-carboxypropanamido]hexanamido]-3-sulfanylpropanamido]butanoic acid
• Synonyms: LeTx I scorpion toxin; Leiurotoxin I; Scyllatoxin

Database IDs

• CAS Number: 116235-63-3
• MDL Number: MFCD00671413
• PubChem SID: 162248064
• PubChem CID: 71311759

CALCULATED PROPERTIES

• Acid pKa: 3.2737904
• H Acceptors: 50
• H Donor: 54
• LogD (pH = 5.5): -31.270533
• LogD (pH = 7.4): -28.30815
• Log P: -20.023613
• Molar Refractivity: 882.9531 cm^3
• Polarizability: 338.4892 Å^3
• Polar Surface Area: 1373.89 Å^2
• Rotatable Bonds: 119
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: lyophilized powder

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥95% (HPLC)
• Shipped in: wet ice
• Recombinant: expressed in E. coli

DETAILS

Sigma Aldrich - S2321

Amino Acid Sequence
Ala-Phe-Cys-Asn-Leu-Arg-Met-Cys-Gln-Leu-Ser-Cys-Arg-Ser-Leu-Gly-Leu-Leu-Gly-Lys-Cys-Ile-Gly-Asp-Lys-Cys-Glu-Cys-Val-Lys-His-NH2
Reconstitution
Stock solution of 1 μm can be obtained by adding 0.292 mL of any conventional buffer per μg of protein.
Biochem/physiol Actions
Recombinant peptide of scyllatoxin, a 31 amino acid long toxin, originally isolated from the venom of the scorpion Leiurus quinquestriatus hebraeus; selective blocker of apamin-sensitive small-conductance Ca2+-activated K+ channels (SK channels) with highest affinity towards Kca2.2.