3-[50-amino-4-(4-aminobutyl)-34,37-bis(3-carbamimidamidopropyl)-40-({3-carbamoyl-1-[(3-carbamoyl-1-{[1-carbamoyl-2-(1H-imidazol-4-yl)ethyl]carbamoyl}propyl)carbamoyl]propyl}carbamoyl)-47-(carbamoylmethyl)-19-(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^{9,13}]tetrapentacontan-16-yl]propanoic acid

• ChemBase ID: 105417
• Molecular Formular: C79H131N31O24S4
• Molecular Mass: 2027.33874
• Monoisotopic Mass: 2025.88660823
• SMILES: CC(C)CC1NC(=O)C(C)NC(=O)C(NC(=O)C(CCC(=O)O)NC(=O)C2CCCN2C(=O)C(C)NC(=O)C(CCCCN)NC(=O)C2CSSCC(NC(=O)C(CCCNC(=N)N)NC(=O)C(CCCNC(=N)N)NC(=O)C(C)NC(=O)C(CSSCC(N)C(=O)NC(CC(=O)N)C(=O)N2)NC1=O)C(=O)NC(CCC(=O)N)C(=O)NC(CCC(=O)N)C(=O)NC(Cc1c[nH]cn1)C(=O)N)C(C)O
• Canonical SMILES: NCCCCC1NC(=O)C2CSSCC(NC(=O)C(CCCNC(=N)N)NC(=O)C(CCCNC(=N)N)NC(=O)C(NC(=O)C(CSSCC(C(=O)NC(C(=O)N2)CC(=O)N)N)NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C2N(C(=O)C(NC1=O)C)CCC2)CCC(=O)O)C(O)C)C)CC(C)C)C)C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N)Cc1c[nH]cn1)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)
• InChIKey: YVIIHEKJCKCXOB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[50-amino-4-(4-aminobutyl)-34,37-bis(3-carbamimidamidopropyl)-40-({3-carbamoyl-1-[(3-carbamoyl-1-{[1-carbamoyl-2-(1H-imidazol-4-yl)ethyl]carbamoyl}propyl)carbamoyl]propyl}carbamoyl)-47-(carbamoylmethyl)-19-(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^{9,13}]tetrapentacontan-16-yl]propanoic acid; 3-[50-amino-4-(4-aminobutyl)-34,37-bis(3-carbamimidamidopropyl)-40-({3-carbamoyl-1-[(3-carbamoyl-1-{[1-carbamoyl-2-(1H-imidazol-5-yl)ethyl]carbamoyl}propyl)carbamoyl]propyl}carbamoyl)-47-(carbamoylmethyl)-19-(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-[50-amino-4-(4-aminobutyl)-34,37-bis(3-carbamimidamidopropyl)-40-({3-carbamoyl-1-[(3-carbamoyl-1-{[1-carbamoyl-2-(1H-imidazol-4-yl)ethyl]carbamoyl}propyl)carbamoyl]propyl}carbamoyl)-47-(carbamoylmethyl)-19-(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^{9,13}]tetrapentacontan-16-yl]propanoic acid; apamin
• Synonyms: APAMIN

Database IDs

• CAS Number: 24345-16-2
• EC Number: 246-182-7
• PubChem SID: 162093606
• PubChem CID: 16129677; 44134548
• CHEMBL: 525408
• Chemspider ID: 23975893
• Wikipedia Title: Apamin

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

Safety Information

• Storage Condition: -20°C
• RTECS: CD6899900
• European Hazard Symbols: Harmful (Xn)
• Risk Statements: R:20
• Safety Statements: S:22-24-26-45-36/37/39

Product Information

• Grade: REAGENT

DETAILS

MP Biomedicals - 02190153

Bee Venom
Reagent Grade
Cys-Asn-Cys-Lys-Ala-Pro-Glu-Thr-Ala-Leu-Cys-Ala-Arg-Cys-Gln-Gln-His-NH₂ . S-S bridge between Cys₁ -Cys_{1 1} and Cys₃ -Cys_{1 7} .

REFERENCES

• Habermann, E., Science , 177 : 314-22 (1972).
• Gauldie, J., et al., Eur. J. Biochem. , 61 : 369-76 (1976).