(2S)-2-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-6-amino-2-[(2S,3S)-2-[(2S)-2-[(2S)-2-[(2S,3S)-2-[(2S)-2-[(2S)-2-{[(2S)-1-[(2S)-2-{2-[(2S,3R)-2-[(2S,3R)-2-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-[(2S)-2-{2-[(2S,3S)-2-(2-aminoacetamido)-3-methylpentanamido]acetamido}propanamido]-3-methylbutanamido]-4-methylpentanamido]hexanamido]-3-methylbutanamido]-4-methylpentanamido]-3-hydroxybutanamido]-3-hydroxybutanamido]acetamido}-4-methylpentanoyl]pyrrolidin-2-yl]formamido}propanamido]-4-methylpentanamido]-3-methylpentanamido]-3-hydroxypropanamido]-3-(1H-indol-3-yl)propanamido]-3-methylpentanamido]hexanamido]-5-carbamimidamidopentanamido]hexanamido]-5-carbamimidamidopentanamido]-4-carbamoylbutanamido]pentanediamide

• ChemBase ID: 106604
• Molecular Formular: C131H229N39O31
• Molecular Mass: 2846.46266
• Monoisotopic Mass: 2844.75417174
• SMILES: CC[C@H](C)[C@H](NC(=O)CN)C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N1CCC[C@H]1C(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@@H](Cc1c[nH]c2c1cccc2)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](CCC(=O)N)C(=O)N
• Canonical SMILES: NCCCC[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)NCC(=O)N[C@H](C(=O)N1CCC[C@H]1C(=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[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N)CCC(=O)N)CCC(=O)N)CCCNC(=N)N)CCCCN)CCCNC(=N)N)CCCCN)[C@H](CC)C)Cc1c[nH]c2c1cccc2)CO)[C@H](CC)C)CC(C)C)C)CC(C)C)[C@H](O)C)[C@H](O)C)CC(C)C)C(C)C)NC(=O)[C@@H](NC(=O)[C@H](C(C)C)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H]([C@H](CC)C)NC(=O)CN)C)CC(C)C
• InChI: InChI=1S/C131H229N39O31/c1-23-71(16)102(163-97(176)60-135)122(194)146-62-98(177)148-74(19)109(181)164-100(69(12)13)124(196)160-88(55-65(4)5)116(188)155-84(41-30-33-51-134)115(187)165-101(70(14)15)125(197)161-90(57-67(8)9)118(190)168-106(77(22)173)128(200)169-105(76(21)172)123(195)147-63-99(178)150-92(58-68(10)11)129(201)170-54-36-44-94(170)121(193)149-75(20)108(180)158-89(56-66(6)7)117(189)166-104(73(18)25-3)127(199)162-93(64-171)120(192)159-91(59-78-61-145-80-38-27-26-37-79(78)80)119(191)167-103(72(17)24-2)126(198)157-83(40-29-32-50-133)111(183)154-85(42-34-52-143-130(139)140)112(184)152-82(39-28-31-49-132)110(182)153-86(43-35-53-144-131(141)142)113(185)156-87(46-48-96(137)175)114(186)151-81(107(138)179)45-47-95(136)174/h26-27,37-38,61,65-77,81-94,100-106,145,171-173H,23-25,28-36,39-60,62-64,132-135H2,1-22H3,(H2,136,174)(H2,137,175)(H2,138,179)(H,146,194)(H,147,195)(H,148,177)(H,149,193)(H,150,178)(H,151,186)(H,152,184)(H,153,182)(H,154,183)(H,155,188)(H,156,185)(H,157,198)(H,158,180)(H,159,192)(H,160,196)(H,161,197)(H,162,199)(H,163,176)(H,164,181)(H,165,187)(H,166,189)(H,167,191)(H,168,190)(H,169,200)(H4,139,140,143)(H4,141,142,144)/t71-,72-,73-,74-,75-,76+,77+,81-,82-,83-,84-,85-,86-,87-,88-,89-,90-,91-,92-,93-,94-,100-,101-,102-,103-,104-,105-,106-/m0/s1
• InChIKey: VDXZNPDIRNWWCW-JFTDCZMZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-6-amino-2-[(2S,3S)-2-[(2S)-2-[(2S)-2-[(2S,3S)-2-[(2S)-2-[(2S)-2-{[(2S)-1-[(2S)-2-{2-[(2S,3R)-2-[(2S,3R)-2-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-[(2S)-2-{2-[(2S,3S)-2-(2-aminoacetamido)-3-methylpentanamido]acetamido}propanamido]-3-methylbutanamido]-4-methylpentanamido]hexanamido]-3-methylbutanamido]-4-methylpentanamido]-3-hydroxybutanamido]-3-hydroxybutanamido]acetamido}-4-methylpentanoyl]pyrrolidin-2-yl]formamido}propanamido]-4-methylpentanamido]-3-methylpentanamido]-3-hydroxypropanamido]-3-(1H-indol-3-yl)propanamido]-3-methylpentanamido]hexanamido]-5-carbamimidamidopentanamido]hexanamido]-5-carbamimidamidopentanamido]-4-carbamoylbutanamido]pentanediamide
• IUPAC Traditional name: (2S)-2-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-6-amino-2-[(2S,3S)-2-[(2S)-2-[(2S)-2-[(2S,3S)-2-[(2S)-2-[(2S)-2-{[(2S)-1-[(2S)-2-{2-[(2S,3R)-2-[(2S,3R)-2-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-[(2S)-2-{2-[(2S,3S)-2-(2-aminoacetamido)-3-methylpentanamido]acetamido}propanamido]-3-methylbutanamido]-4-methylpentanamido]hexanamido]-3-methylbutanamido]-4-methylpentanamido]-3-hydroxybutanamido]-3-hydroxybutanamido]acetamido}-4-methylpentanoyl]pyrrolidin-2-yl]formamido}propanamido]-4-methylpentanamido]-3-methylpentanamido]-3-hydroxypropanamido]-3-(1H-indol-3-yl)propanamido]-3-methylpentanamido]hexanamido]-5-carbamimidamidopentanamido]hexanamido]-5-carbamimidamidopentanamido]-4-carbamoylbutanamido]pentanediamide
• Synonyms: GIGAVLKVLTTGLPALISWIKRKRQQ-NH2; GIGAVLKVLTTGLPALISWIKRKRQQ-NH2 MELITTIN; Melittin; Melittin from honey bee venom; Melittin

Database IDs

• CAS Number: 20449-79-0; 37231-28-0
• EC Number: 253-417-7
• MDL Number: MFCD00076868
• PubChem SID: 162087302; 24896718; 24896910
• PubChem CID: 16133648
• CHEMBL: 412927
• Chemspider ID: 17290230
• MeSH Name: Melitten
• Wikipedia Title: Melittin

CALCULATED PROPERTIES

• H Acceptors: 41
• H Donor: 41
• LogD (pH = 5.5): -26.697006
• LogD (pH = 7.4): -23.742332
• Log P: -10.533494
• Molar Refractivity: 755.6249 cm^3
• Polarizability: 289.77097 Å^3
• Polar Surface Area: 1152.34 Å^2
• Rotatable Bonds: 97
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Flash Point: 112 °C; 233.6 °F

Safety Information

• RTECS: OS3960000; OS3965000
• European Hazard Symbols: Toxic (T); Harmful (Xn)
• UN Number: 3462
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 1
• Risk Statements: 21/22; 23/24/25
• Safety Statements: 36; 36/37/39-45
• GHS Pictograms: GHS06; GHS07
• GHS Signal Word: Danger; Warning
• GHS Hazard statements: H301-H311-H331; H302-H312
• GHS Precautionary statements: P261-P280-P301 + P310-P311; P280
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves; Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 3462 6.1/PG 1
• Storage Temperature: -20°C; 2-8°C

Pharmacology Properties

• Gene Information: human ... ATP1A1(476), CALM1(801)mouse ... ATP1A1(11928), CALM1(12313)rat ... ATP1A1(24211), CALM1(24242)

Product Information

• Purity: ~70% (HPLC); ≥85% (HPLC); ≥90% (HPLC); ≥97% (HPLC); 65-85% (HPLC)
• Packaging: vial of 100 μg
• Foreign Activity: Phospholipase A2 ≤0.5%; Phospholipase A2 ≤2%
• Empirical Formula (Hill Notation): C131H229N39O31

DETAILS

MP Biomedicals - 03PKS043

MELITTIN

Sigma Aldrich - M2272

Amino Acid Sequence
Gly-Ile-Gly-Ala-Val-Leu-Lys-Val-Leu-Thr-Thr-Gly-Leu-Pro-Ala-Leu-Ile-Ser-Trp-Ile-Lys-Arg-Lys-Arg-Gln-Gln-NH2
Biochem/physiol Actions
Binds calmodulin in a Ca2+-dependent manner; inhibits Na+-K+-ATPase.
Other Notes
The principle hemolytic component of honeybee venom.

Sigma Aldrich - M4171

Amino Acid Sequence
Gly-Ile-Gly-Ala-Val-Leu-Lys-Val-Leu-Thr-Thr-Gly-Leu-Pro-Ala-Leu-Ile-Ser-Trp-Ile-Lys-Arg-Lys-Arg-Gln-Gln-NH2
Biochem/physiol Actions
Binds calmodulin in a Ca2+-dependent manner; inhibits Na+-K+-ATPase.
Other Notes
The principle hemolytic component of honeybee venom.

Sigma Aldrich - M1407

Amino Acid Sequence
Gly-Ile-Gly-Ala-Val-Leu-Lys-Val-Leu-Thr-Thr-Gly-Leu-Pro-Ala-Leu-Ile-Ser-Trp-Ile-Lys-Arg-Lys-Arg-Gln-Gln-NH2
Biochem/physiol Actions
Binds calmodulin in a Ca2+-dependent manner; inhibits Na+-K+-ATPase.
Other Notes
The principle hemolytic component of honeybee venom.
Preparation Note
HPLC-purified and use tested as a protease substrate.

Sigma Aldrich - M7391

Amino Acid Sequence
Gly-Ile-Gly-Ala-Val-Leu-Lys-Val-Leu-Thr-Thr-Gly-Leu-Pro-Ala-Leu-Ile-Ser-Trp-Ile-Lys-Arg-Lys-Arg-Gln-Gln-NH2
Biochem/physiol Actions
Binds calmodulin in a Ca2+-dependent manner; inhibits Na+-K+-ATPase.
Other Notes
The principle hemolytic component of honeybee venom.

Sigma Aldrich - 63650

Amino Acid Sequence
Gly-Ile-Gly-Ala-Val-Leu-Lys-Val-Leu-Thr-Thr-Gly-Leu-Pro-Ala-Leu-Ile-Ser-Trp-Ile-Lys-Arg-Lys-Arg-Gln-Gln-NH2
Biochem/physiol Actions
Binds calmodulin in a Ca2+-dependent manner; inhibits Na+-K+-ATPase.
Other Notes
The principle hemolytic component of honeybee venom.
Main component of the honeybee venom. It is a basic hydrophobic peptide which alters membrane permeability1; Interference with enzymes2; Interaction with calmodulin3; Used in the affinity chromatographic purification of calmodulin4