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

• ChemBase ID: 155572
• Molecular Formular: C70H132N20O15
• Molecular Mass: 1493.92208
• Monoisotopic Mass: 1493.01810362
• 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](CCCCN)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](CC(C)C)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)CC(C)C)CC(C)C)CCCCN)CCCCN)C)CC(C)C)C)C)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)CC(C)C)CCCCN)C
• InChI: InChI=1S/C70H132N20O15/c1-15-41(10)56(76)70(105)90-54(36-55(75)91)69(104)89-52(34-39(6)7)67(102)85-47(25-17-21-29-72)63(98)80-44(13)59(94)82-46(24-16-20-28-71)62(97)79-42(11)58(93)78-43(12)61(96)87-51(33-38(4)5)66(101)81-45(14)60(95)83-48(26-18-22-30-73)64(99)84-49(27-19-23-31-74)65(100)88-53(35-40(8)9)68(103)86-50(57(77)92)32-37(2)3/h37-54,56H,15-36,71-74,76H2,1-14H3,(H2,75,91)(H2,77,92)(H,78,93)(H,79,97)(H,80,98)(H,81,101)(H,82,94)(H,83,95)(H,84,99)(H,85,102)(H,86,103)(H,87,96)(H,88,100)(H,89,104)(H,90,105)/t41-,42-,43-,44-,45-,46-,47-,48-,49-,50-,51-,52-,53-,54-,56-/m0/s1
• InChIKey: TUCDQOGRFHOSKG-ZWFWRLIFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-N-[(1S)-1-{[(1S)-5-amino-1-{[(1S)-1-{[(1S)-5-amino-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-5-amino-1-{[(1S)-5-amino-1-{[(1S)-1-{[(1S)-1-carbamoyl-3-methylbutyl]carbamoyl}-3-methylbutyl]carbamoyl}pentyl]carbamoyl}pentyl]carbamoyl}ethyl]carbamoyl}-3-methylbutyl]carbamoyl}ethyl]carbamoyl}ethyl]carbamoyl}pentyl]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)-5-amino-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-5-amino-1-{[(1S)-5-amino-1-{[(1S)-1-{[(1S)-1-carbamoyl-3-methylbutyl]carbamoyl}-3-methylbutyl]carbamoyl}pentyl]carbamoyl}pentyl]carbamoyl}ethyl]carbamoyl}-3-methylbutyl]carbamoyl}ethyl]carbamoyl}ethyl]carbamoyl}pentyl]carbamoyl}ethyl]carbamoyl}pentyl]carbamoyl}-3-methylbutyl]-2-[(2S,3S)-2-amino-3-methylpentanamido]butanediamide
• Synonyms: Mas 17; Mastoparan 17

Database IDs

• CAS Number: 145854-61-1
• MDL Number: MFCD00144725
• PubChem SID: 162249710
• PubChem CID: 71312157

CALCULATED PROPERTIES

• Acid pKa: 11.908604
• H Acceptors: 20
• H Donor: 20
• LogD (pH = 5.5): -18.62329
• LogD (pH = 7.4): -15.269431
• Log P: -3.9882536
• Molar Refractivity: 392.5831 cm^3
• Polarizability: 155.64595 Å^3
• Polar Surface Area: 594.58 Å^2
• Rotatable Bonds: 55
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: lyophilized 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

Product Information

• Purity: ≥96.5%
• Empirical Formula (Hill Notation): C70H132N20O15

DETAILS

Sigma Aldrich - M213

Amino Acid Sequence
Ile-Asn-Leu-Lys-Ala-Lys-Ala-Ala-Leu-Ala-Lys-Lys-Leu-Leu-NH2
Biochem/physiol Actions
Inactive analog of mastoparan; useful as negative control.
Caution
Hygroscopic