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

• ChemBase ID: 132083
• Molecular Formular: C67H124N18O15
• Molecular Mass: 1421.81306
• Monoisotopic Mass: 1420.94935536
• SMILES: CCCC[C@@H](C(=O)N)NC(=O)[C@H](CCCC)NC(=O)[C@H](C)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@H](CCCC)NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CCCC)NC(=O)[C@H](C)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCCC)NC(=O)[C@H](CC(=O)N)NC(=O)[C@H]([C@@H](C)CC)N
• Canonical SMILES: CCCC[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)CCCC)CCCC)C)CCCCN)C)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]([C@H](CC)C)N)CC(=O)N)CCCC)CCCCN)C)CCCC)C)C
• InChI: InChI=1S/C67H124N18O15/c1-13-19-28-44(54(72)87)78-64(97)47(31-22-16-4)81-58(91)42(11)76-62(95)49(33-24-26-35-68)82-59(92)43(12)75-61(94)46(30-21-15-3)79-56(89)40(9)73-55(88)39(8)74-60(93)45(29-20-14-2)80-57(90)41(10)77-63(96)50(34-25-27-36-69)83-65(98)48(32-23-17-5)84-66(99)51(37-52(70)86)85-67(100)53(71)38(7)18-6/h38-51,53H,13-37,68-69,71H2,1-12H3,(H2,70,86)(H2,72,87)(H,73,88)(H,74,93)(H,75,94)(H,76,95)(H,77,96)(H,78,97)(H,79,89)(H,80,90)(H,81,91)(H,82,92)(H,83,98)(H,84,99)(H,85,100)/t38-,39-,40-,41-,42-,43-,44-,45-,46-,47-,48-,49-,50-,51-,53-/m0/s1
• InChIKey: FTHYLJMZIHSPNX-FGRXCANLSA-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)-1-{[(1S)-1-{[(1S)-1-carbamoylpentyl]carbamoyl}pentyl]carbamoyl}ethyl]carbamoyl}pentyl]carbamoyl}ethyl]carbamoyl}pentyl]carbamoyl}ethyl]carbamoyl}ethyl]carbamoyl}pentyl]carbamoyl}ethyl]carbamoyl}pentyl]carbamoyl}pentyl]-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)-1-{[(1S)-1-{[(1S)-1-carbamoylpentyl]carbamoyl}pentyl]carbamoyl}ethyl]carbamoyl}pentyl]carbamoyl}ethyl]carbamoyl}pentyl]carbamoyl}ethyl]carbamoyl}ethyl]carbamoyl}pentyl]carbamoyl}ethyl]carbamoyl}pentyl]carbamoyl}pentyl]-2-[(2S,3S)-2-amino-3-methylpentanamido]butanediamide
• Synonyms: Mastoparan from Polistes jadwagae

Database IDs

• CAS Number: 145854-59-7
• PubChem SID: 162226360
• PubChem CID: 71308515

CALCULATED PROPERTIES

• Acid pKa: 11.7073965
• H Acceptors: 18
• H Donor: 18
• LogD (pH = 5.5): -10.269633
• LogD (pH = 7.4): -7.7551765
• Log P: -1.6825943
• Molar Refractivity: 371.8943 cm^3
• Polarizability: 147.0909 Å^3
• Polar Surface Area: 542.54 Å^2
• Rotatable Bonds: 54
• Lipinski's Rule of Five: false

PROPERTIES

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: ≥97% (HPLC)

DETAILS

Sigma Aldrich - M3545

Biochem/physiol Actions
Mast cell degranulating peptide. Activates phospholipase A2; inhibits calmodulin. Cell permeable; stimulates exocytosis and phosphoinositide breakdown.