3-[(1R,4S,7S,13S,16S,19S,22S,25S,28R,31S,34S,37S,40R,47S,50R)-50-amino-4-(4-aminobutyl)-34,37-bis(3-carbamimidamidopropyl)-40-{[(1S)-3-carbamoyl-1-{[(1S)-3-carbamoyl-1-{[(1S)-1-carbamoyl-2-(1H-imidazol-5-yl)ethyl]carbamoyl}propyl]carbamoyl}propyl]carbamoyl}-47-(carbamoylmethyl)-19-[(1R)-1-hydroxyethyl]-7,22,31-trimethyl-25-(2-methylpropyl)-2,5,8,14,17,20,23,26,29,32,35,38,46,49-tetradecaoxo-42,43,52,53-tetrathia-3,6,9,15,18,21,24,27,30,33,36,39,45,48-tetradecaazatricyclo[26.16.10.09,13]tetrapentacontan-16-yl]propanoic acid

• ChemBase ID: 155183
• Molecular Formular: C79H131N31O24S4
• Molecular Mass: 2027.33874
• Monoisotopic Mass: 2025.88660823
• SMILES: C[C@H]1C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](CSSC[C@H]2C(=O)N[C@H](C(=O)N[C@H](C(=O)N3CCC[C@H]3C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@@H](CSSC[C@@H](C(=O)N[C@H](C(=O)N2)CC(=O)N)N)C(=O)N1)CC(C)C)C)[C@@H](C)O)CCC(=O)O)C)CCCCN)C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](Cc1cnc[nH]1)C(=O)N)CCCNC(=N)N)CCCNC(=N)N
• Canonical SMILES: NCCCC[C@@H]1NC(=O)[C@@H]2CSSC[C@H](NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](NC(=O)[C@H](CSSC[C@@H](C(=O)N[C@H](C(=O)N2)CC(=O)N)N)NC(=O)[C@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](NC(=O)[C@H]2N(C(=O)[C@@H](NC1=O)C)CCC2)CCC(=O)O)[C@H](O)C)C)CC(C)C)C)C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N)Cc1cnc[nH]1)CCC(=O)N)CCC(=O)N
• InChI: InChI=1S/C79H131N31O24S4/c1-35(2)26-49-70(127)107-51-31-136-135-30-41(81)63(120)105-50(28-57(84)114)71(128)108-53(73(130)99-42(12-7-8-22-80)64(121)96-38(5)77(134)110-25-11-15-54(110)75(132)102-47(18-21-58(115)116)69(126)109-59(39(6)111)76(133)95-37(4)62(119)104-49)33-138-137-32-52(106-66(123)44(14-10-24-92-79(88)89)98-65(122)43(13-9-23-91-78(86)87)97-61(118)36(3)94-72(51)129)74(131)101-45(16-19-55(82)112)67(124)100-46(17-20-56(83)113)68(125)103-48(60(85)117)27-40-29-90-34-93-40/h29,34-39,41-54,59,111H,7-28,30-33,80-81H2,1-6H3,(H2,82,112)(H2,83,113)(H2,84,114)(H2,85,117)(H,90,93)(H,94,129)(H,95,133)(H,96,121)(H,97,118)(H,98,122)(H,99,130)(H,100,124)(H,101,131)(H,102,132)(H,103,125)(H,104,119)(H,105,120)(H,106,123)(H,107,127)(H,108,128)(H,109,126)(H,115,116)(H4,86,87,91)(H4,88,89,92)/t36?,37-,38-,39+,41-,42-,43-,44?,45-,46-,47-,48-,49-,50-,51-,52-,53-,54-,59-/m0/s1
• InChIKey: YVIIHEKJCKCXOB-MLWYPRIZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[(1R,4S,7S,13S,16S,19S,22S,25S,28R,31S,34S,37S,40R,47S,50R)-50-amino-4-(4-aminobutyl)-34,37-bis(3-carbamimidamidopropyl)-40-{[(1S)-3-carbamoyl-1-{[(1S)-3-carbamoyl-1-{[(1S)-1-carbamoyl-2-(1H-imidazol-5-yl)ethyl]carbamoyl}propyl]carbamoyl}propyl]carbamoyl}-47-(carbamoylmethyl)-19-[(1R)-1-hydroxyethyl]-7,22,31-trimethyl-25-(2-methylpropyl)-2,5,8,14,17,20,23,26,29,32,35,38,46,49-tetradecaoxo-42,43,52,53-tetrathia-3,6,9,15,18,21,24,27,30,33,36,39,45,48-tetradecaazatricyclo[26.16.10.0^9,^1^3]tetrapentacontan-16-yl]propanoic acid
• IUPAC Traditional name: 3-[(1R,4S,7S,13S,16S,19S,22S,25S,28R,31S,34S,37S,40R,47S,50R)-50-amino-4-(4-aminobutyl)-34,37-bis(3-carbamimidamidopropyl)-40-{[(1S)-3-carbamoyl-1-{[(1S)-3-carbamoyl-1-{[(1S)-1-carbamoyl-2-(3H-imidazol-4-yl)ethyl]carbamoyl}propyl]carbamoyl}propyl]carbamoyl}-47-(carbamoylmethyl)-19-[(1R)-1-hydroxyethyl]-7,22,31-trimethyl-25-(2-methylpropyl)-2,5,8,14,17,20,23,26,29,32,35,38,46,49-tetradecaoxo-42,43,52,53-tetrathia-3,6,9,15,18,21,24,27,30,33,36,39,45,48-tetradecaazatricyclo[26.16.10.0^9,^1^3]tetrapentacontan-16-yl]propanoic acid
• Synonyms: Apamin

Database IDs

• CAS Number: 24345-16-2
• EC Number: 246-182-7
• MDL Number: MFCD00167944
• PubChem SID: 162249321; 24891455; 24890526
• PubChem CID: 16218850

CALCULATED PROPERTIES

• Acid pKa: 3.6373796
• H Acceptors: 33
• H Donor: 31
• LogD (pH = 5.5): -26.611021
• LogD (pH = 7.4): -24.055582
• Log P: -18.840696
• Molar Refractivity: 517.0536 cm^3
• Polarizability: 193.83539 Å^3
• Polar Surface Area: 920.32 Å^2
• Rotatable Bonds: 35
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: 0.05 M acetic acid: soluble5 mg/mL, clear, colorless to faintly yellow

Safety Information

• RTECS: CD6899900
• German water hazard class: 3
• Safety Statements: 22-24/25
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: rat ... Kcnn1(54261)

Product Information

• Purity: ≥80% peptide basis; ≥95% (HPLC); ≥97% (HPLC)
• Biological Source: from bee venom; synthetic
• Empirical Formula (Hill Notation): C79H131N31O24S4

DETAILS

Sigma Aldrich - A9459

Amino Acid Sequence
Cys-Asn-Cys-Lys-Ala-Pro-Glu-Thr-Ala-Leu-Cys-Ala-Arg-Arg-Cys-Gln-Gln-His-NH2 [Disulfide Bridges: 1-11, 3-15]
Biochem/physiol Actions
The only polypeptide neurotoxin that is known to pass the blood-brain barrier. Blocks ATP-type Ca+2-activated K+ channels.

Sigma Aldrich - A1289

Amino Acid Sequence
Cys-Asn-Cys-Lys-Ala-Pro-Glu-Thr-Ala-Leu-Cys-Ala-Arg-Arg-Cys-Gln-Gln-His-NH2 [Disulfide Bridges: 1-11, 3-15]
Biochem/physiol Actions
The only polypeptide neurotoxin that is known to pass the blood-brain barrier. Blocks ATP-type Ca+2-activated K+ channels.

Sigma Aldrich - 10796

Amino Acid Sequence
Cys-Asn-Cys-Lys-Ala-Pro-Glu-Thr-Ala-Leu-Cys-Ala-Arg-Arg-Cys-Gln-Gln-His-NH2 [Disulfide Bridges: 1-11, 3-15]
Biochem/physiol Actions
The only polypeptide neurotoxin that is known to pass the blood-brain barrier. Blocks ATP-type Ca+2-activated K+ channels.
Other Notes
A neurotoxin which blocks a class of Ca2+-activated K+ channels1; Biochemistry and pharmacology of2