(2S)-2-[(2S)-2-[(2R)-2-[(2S)-2-[(2S)-2-(2-{[(2S,4R)-1-[(2S)-1-[(2S)-2-[(2S)-6-amino-2-[(2S)-2,6-diaminohexanamido]hexanamido]-5-carbamimidamidopentanoyl]pyrrolidine-2-carbonyl]-4-hydroxypyrrolidin-2-yl]formamido}acetamido)-3-(thiophen-2-yl)propanamido]-3-hydroxypropanamido]-3-phenylpropanamido]-3-(thiophen-2-yl)propanamido]-5-carbamimidamidopentanoic acid

• ChemBase ID: 153798
• Molecular Formular: C62H95N19O14S2
• Molecular Mass: 1394.6666
• Monoisotopic Mass: 1393.67473082
• SMILES: c1ccc(cc1)C[C@H](C(=O)N[C@@H](Cc1cccs1)C(=O)N[C@@H](CCCNC(=N)N)C(=O)O)NC(=O)[C@H](CO)NC(=O)[C@H](Cc1cccs1)NC(=O)CNC(=O)[C@@H]1C[C@H](CN1C(=O)[C@@H]1CCCN1C(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCCCN)N)O
• Canonical SMILES: NCCCC[C@@H](C(=O)N[C@H](C(=O)N1CCC[C@H]1C(=O)N1C[C@@H](C[C@H]1C(=O)NCC(=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)O)CCCNC(=N)N)Cc1cccs1)Cc1ccccc1)CO)Cc1cccs1)O)CCCNC(=N)N)NC(=O)[C@H](CCCCN)N
• InChI: InChI=1S/C62H95N19O14S2/c63-22-6-4-17-40(65)51(85)74-41(18-5-7-23-64)52(86)75-42(19-8-24-70-61(66)67)58(92)80-26-10-21-48(80)59(93)81-34-37(83)30-49(81)57(91)72-33-50(84)73-45(31-38-15-11-27-96-38)54(88)79-47(35-82)56(90)77-44(29-36-13-2-1-3-14-36)53(87)78-46(32-39-16-12-28-97-39)55(89)76-43(60(94)95)20-9-25-71-62(68)69/h1-3,11-16,27-28,37,40-49,82-83H,4-10,17-26,29-35,63-65H2,(H,72,91)(H,73,84)(H,74,85)(H,75,86)(H,76,89)(H,77,90)(H,78,87)(H,79,88)(H,94,95)(H4,66,67,70)(H4,68,69,71)/t37-,40+,41+,42+,43+,44-,45+,46+,47+,48+,49+/m1/s1
• InChIKey: BAPXVPGXAHEAKB-BYZYXFGASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(2S)-2-[(2R)-2-[(2S)-2-[(2S)-2-(2-{[(2S,4R)-1-[(2S)-1-[(2S)-2-[(2S)-6-amino-2-[(2S)-2,6-diaminohexanamido]hexanamido]-5-carbamimidamidopentanoyl]pyrrolidine-2-carbonyl]-4-hydroxypyrrolidin-2-yl]formamido}acetamido)-3-(thiophen-2-yl)propanamido]-3-hydroxypropanamido]-3-phenylpropanamido]-3-(thiophen-2-yl)propanamido]-5-carbamimidamidopentanoic acid
• IUPAC Traditional name: (2S)-2-[(2S)-2-[(2R)-2-[(2S)-2-[(2S)-2-(2-{[(2S,4R)-1-[(2S)-1-[(2S)-2-[(2S)-6-amino-2-[(2S)-2,6-diaminohexanamido]hexanamido]-5-carbamimidamidopentanoyl]pyrrolidine-2-carbonyl]-4-hydroxypyrrolidin-2-yl]formamido}acetamido)-3-(thiophen-2-yl)propanamido]-3-hydroxypropanamido]-3-phenylpropanamido]-3-(thiophen-2-yl)propanamido]-5-carbamimidamidopentanoic acid
• Synonyms: Lys-Lys-(Hyp3,β-(2-thienyl)-Ala5,8,D-Phe7)-Bradykinin

Database IDs

• MDL Number: MFCD00076278
• PubChem SID: 162247937
• PubChem CID: 71311733

CALCULATED PROPERTIES

• Acid pKa: 3.9127042
• H Acceptors: 23
• H Donor: 20
• LogD (pH = 5.5): -18.061825
• LogD (pH = 7.4): -15.524022
• Log P: -7.4021482
• Molar Refractivity: 376.5508 cm^3
• Polarizability: 138.57071 Å^3
• Polar Surface Area: 553.04 Å^2
• Rotatable Bonds: 42
• 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

• Compostion: Peptide content, ≥70%
• Empirical Formula (Hill Notation): C62H95N19O14S2

DETAILS

Sigma Aldrich - B5309

Amino Acid Sequence
Lys-Lys-Arg-Pro-Hyp-Gly-β-(2-thienyl)-Ala-Ser-D-Phe-β-(2-thienyl)-Ala-Arg-OH
Biochem/physiol Actions
An analog of bradykinin which is a specific inhibitor of five different actions of bradykinin.