(2S)-2-[(2S)-2-{[(2S)-1-[(2S)-2-{[(2S)-1-{2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-amino-4-(methylsulfanyl)butanamido]hexanamido]-5-carbamimidamidopentanamido]-3-hydroxypropanamido]-5-carbamimidamidopentanamido]acetyl}pyrrolidin-2-yl]formamido}-3-hydroxypropanoyl]pyrrolidin-2-yl]formamido}-5-carbamimidamidopentanamido]-5-carbamimidamidopentanoic acid

• ChemBase ID: 133502
• Molecular Formular: C53H98N24O14S
• Molecular Mass: 1327.56262
• Monoisotopic Mass: 1326.74150494
• SMILES: CSCC[C@@H](C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCNC(=N)N)C(=O)NCC(=O)N1CCC[C@H]1C(=O)N[C@@H](CO)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CCCNC(=N)N)C(=O)O)N
• Canonical SMILES: NCCCC[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)NCC(=O)N1CCC[C@H]1C(=O)N[C@H](C(=O)N1CCC[C@H]1C(=O)N[C@H](C(=O)N[C@H](C(=O)O)CCCNC(=N)N)CCCNC(=N)N)CO)CCCNC(=N)N)CO)CCCNC(=N)N)NC(=O)[C@H](CCSC)N
• InChI: InChI=1S/C53H98N24O14S/c1-92-25-17-29(55)40(81)69-31(10-2-3-18-54)42(83)71-32(12-5-20-65-51(58)59)44(85)74-35(27-78)45(86)70-30(11-4-19-64-50(56)57)41(82)68-26-39(80)76-23-8-15-37(76)46(87)75-36(28-79)48(89)77-24-9-16-38(77)47(88)72-33(13-6-21-66-52(60)61)43(84)73-34(49(90)91)14-7-22-67-53(62)63/h29-38,78-79H,2-28,54-55H2,1H3,(H,68,82)(H,69,81)(H,70,86)(H,71,83)(H,72,88)(H,73,84)(H,74,85)(H,75,87)(H,90,91)(H4,56,57,64)(H4,58,59,65)(H4,60,61,66)(H4,62,63,67)/t29-,30-,31-,32-,33-,34-,35-,36-,37-,38-/m0/s1
• InChIKey: XXSQKDSFQHDKRK-YRYMBYOHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(2S)-2-{[(2S)-1-[(2S)-2-{[(2S)-1-{2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-amino-4-(methylsulfanyl)butanamido]hexanamido]-5-carbamimidamidopentanamido]-3-hydroxypropanamido]-5-carbamimidamidopentanamido]acetyl}pyrrolidin-2-yl]formamido}-3-hydroxypropanoyl]pyrrolidin-2-yl]formamido}-5-carbamimidamidopentanamido]-5-carbamimidamidopentanoic acid
• IUPAC Traditional name: (2S)-2-[(2S)-2-{[(2S)-1-[(2S)-2-{[(2S)-1-{2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-amino-4-(methylsulfanyl)butanamido]hexanamido]-5-carbamimidamidopentanamido]-3-hydroxypropanamido]-5-carbamimidamidopentanamido]acetyl}pyrrolidin-2-yl]formamido}-3-hydroxypropanoyl]pyrrolidin-2-yl]formamido}-5-carbamimidamidopentanamido]-5-carbamimidamidopentanoic acid
• Synonyms: Met-Lys-Arg-Ser-Arg-Gly-Pro-Ser-Pro-Arg-Arg; Met-Lys-[Ser2, Arg3, Pro5, Arg8]-Bradykinin

Database IDs

• CAS Number: 165174-60-7
• MDL Number: MFCD00238087
• PubChem SID: 162227779
• PubChem CID: 71308680

CALCULATED PROPERTIES

• Acid pKa: -1.0179062
• H Acceptors: 28
• H Donor: 25
• LogD (pH = 5.5): -25.576105
• LogD (pH = 7.4): -23.45448
• Log P: -13.409757
• Molar Refractivity: 375.5471 cm^3
• Polarizability: 129.40442 Å^3
• Polar Surface Area: 650.82 Å^2
• Rotatable Bonds: 44
• 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)
• Compostion: Peptide content, ~65%

DETAILS

Sigma Aldrich - M0421

Amino Acid Sequence
Met-Lys-Arg-Ser-Arg-Gly-Pro-Ser-Pro-Arg-Arg
Other Notes
A neuropeptide found in Aplysia californica with high sequence homology to bradykinin and kallidin.