(2S)-N-[(1S)-1-{[(1S)-5-amino-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-5-amino-1-{[(1S)-5-amino-1-{[(1S,2S)-1-{[(1S)-1-carbamoyl-3-methylbutyl]carbamoyl}-2-methylbutyl]carbamoyl}pentyl]carbamoyl}pentyl]carbamoyl}ethyl]carbamoyl}-3-methylbutyl]carbamoyl}ethyl]carbamoyl}ethyl]carbamoyl}-3-methylbutyl]carbamoyl}ethyl]carbamoyl}pentyl]carbamoyl}-3-methylbutyl]-2-[(2S,3S)-2-amino-3-methylpentanamido]butanediamide

• ChemBase ID: 133762
• Molecular Formular: C70H131N19O15
• Molecular Mass: 1478.90744
• Monoisotopic Mass: 1478.00720459
• SMILES: CC[C@H](C)[C@@H](C(=O)N[C@@H](CC(=O)N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC(C)C)C(=O)N)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)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)CC(C)C)[C@H](CC)C)CCCCN)CCCCN)C)CC(C)C)C)C)CC(C)C)C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H]([C@H](CC)C)N)CC(=O)N)CC(C)C
• InChI: InChI=1S/C70H131N19O15/c1-17-40(11)55(75)69(103)88-53(35-54(74)90)68(102)87-52(34-39(9)10)67(101)83-46(25-19-22-28-71)62(96)78-45(16)61(95)86-50(32-37(5)6)65(99)79-42(13)58(92)77-43(14)60(94)85-51(33-38(7)8)66(100)80-44(15)59(93)81-47(26-20-23-29-72)63(97)82-48(27-21-24-30-73)64(98)89-56(41(12)18-2)70(104)84-49(57(76)91)31-36(3)4/h36-53,55-56H,17-35,71-73,75H2,1-16H3,(H2,74,90)(H2,76,91)(H,77,92)(H,78,96)(H,79,99)(H,80,100)(H,81,93)(H,82,97)(H,83,101)(H,84,104)(H,85,94)(H,86,95)(H,87,102)(H,88,103)(H,89,98)/t40-,41-,42-,43-,44-,45-,46-,47-,48-,49-,50-,51-,52-,53-,55-,56-/m0/s1
• InChIKey: MASXKPLGZRMBJF-MVSGICTGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-N-[(1S)-1-{[(1S)-5-amino-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-5-amino-1-{[(1S)-5-amino-1-{[(1S,2S)-1-{[(1S)-1-carbamoyl-3-methylbutyl]carbamoyl}-2-methylbutyl]carbamoyl}pentyl]carbamoyl}pentyl]carbamoyl}ethyl]carbamoyl}-3-methylbutyl]carbamoyl}ethyl]carbamoyl}ethyl]carbamoyl}-3-methylbutyl]carbamoyl}ethyl]carbamoyl}pentyl]carbamoyl}-3-methylbutyl]-2-[(2S,3S)-2-amino-3-methylpentanamido]butanediamide
• IUPAC Traditional name: (2S)-N-[(1S)-1-{[(1S)-5-amino-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-5-amino-1-{[(1S)-5-amino-1-{[(1S,2S)-1-{[(1S)-1-carbamoyl-3-methylbutyl]carbamoyl}-2-methylbutyl]carbamoyl}pentyl]carbamoyl}pentyl]carbamoyl}ethyl]carbamoyl}-3-methylbutyl]carbamoyl}ethyl]carbamoyl}ethyl]carbamoyl}-3-methylbutyl]carbamoyl}ethyl]carbamoyl}pentyl]carbamoyl}-3-methylbutyl]-2-[(2S,3S)-2-amino-3-methylpentanamido]butanediamide
• Synonyms: Mastoparan, Vespula lewisii

Database IDs

• CAS Number: 72093-21-1
• MDL Number: MFCD00076865
• Beilstein Number: 5491949
• PubChem SID: 162228039
• PubChem CID: 6324633

CALCULATED PROPERTIES

• Acid pKa: 11.774585
• H Acceptors: 19
• H Donor: 19
• LogD (pH = 5.5): -14.1353245
• LogD (pH = 7.4): -11.201008
• Log P: -2.5242891
• Molar Refractivity: 388.8675 cm^3
• Polarizability: 154.11646 Å^3
• Polar Surface Area: 568.56 Å^2
• Rotatable Bonds: 53
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

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

Pharmacology Properties

• Gene Information: human ... CALM1(801), PLA2R1(22925)mouse ... CALM1(12313), PLA2R1(18779)rat ... CALM1(24242), PLA2R1(295631)

Product Information

• Purity: ≥70% peptide basis; ≥96.0% (HPLC); ≥97% (HPLC)
• Biological Source: synthetic
• Empirical Formula (Hill Notation): C70H131N19O15

DETAILS

Sigma Aldrich - M5280

Amino Acid Sequence
Ile-Asn-Leu-Lys-Ala-Leu-Ala-Ala-Leu-Ala-Lys-Lys-Ile-Leu-NH2
Biochem/physiol Actions
Mast cell degranulating peptide. Activates phospholipase A2; inhibits calmodulin. Cell permeable; stimulates exocytosis and phosphoinositide breakdown.

Sigma Aldrich - 63589

Amino Acid Sequence
Ile-Asn-Leu-Lys-Ala-Leu-Ala-Ala-Leu-Ala-Lys-Lys-Ile-Leu-NH2
Biochem/physiol Actions
Mast cell degranulating peptide. Activates phospholipase A2; inhibits calmodulin. Cell permeable; stimulates exocytosis and phosphoinositide breakdown.
Other Notes
A peptide toxin from wasp venom - a non-specific secretagogue. Mastoparan-stimulated G-protein function1