(2S,3S)-2-[(2R)-2-[(2S)-2-[(2S)-2-(2-{[(2S)-1-[(2S)-1-[(2S)-2-[(2S)-6-amino-2-acetamidohexanamido]-5-carbamimidamidopentanoyl]pyrrolidine-2-carbonyl]pyrrolidin-2-yl]formamido}acetamido)-3-phenylpropanamido]-3-hydroxypropanamido]-3-(naphthalen-2-yl)propanamido]-3-methylpentanoic acid; trifluoroacetic acid

• ChemBase ID: 154629
• Molecular Formular: C59H82F3N13O14
• Molecular Mass: 1254.3562896
• Monoisotopic Mass: 1253.60562903
• SMILES: CC[C@H](C)[C@@H](C(=O)O)NC(=O)[C@@H](Cc1ccc2ccccc2c1)NC(=O)[C@H](CO)NC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)[C@@H]1CCCN1C(=O)[C@@H]1CCCN1C(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CCCCN)NC(=O)C.C(=O)(C(F)(F)F)O
• Canonical SMILES: OC(=O)C(F)(F)F.NCCCC[C@@H](C(=O)N[C@H](C(=O)N1CCC[C@H]1C(=O)N1CCC[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@H](CC)C)C(=O)O)Cc1ccc2c(c1)cccc2)CO)Cc1ccccc1)CCCNC(=N)N)NC(=O)C
• InChI: InChI=1S/C57H81N13O12.C2HF3O2/c1-4-34(2)48(56(81)82)68-51(76)43(31-37-23-24-38-17-8-9-18-39(38)29-37)66-52(77)44(33-71)67-50(75)42(30-36-15-6-5-7-16-36)64-47(73)32-62-53(78)45-21-13-27-69(45)55(80)46-22-14-28-70(46)54(79)41(20-12-26-61-57(59)60)65-49(74)40(63-35(3)72)19-10-11-25-58;3-2(4,5)1(6)7/h5-9,15-18,23-24,29,34,40-46,48,71H,4,10-14,19-22,25-28,30-33,58H2,1-3H3,(H,62,78)(H,63,72)(H,64,73)(H,65,74)(H,66,77)(H,67,75)(H,68,76)(H,81,82)(H4,59,60,61);(H,6,7)/t34-,40-,41-,42-,43+,44-,45-,46-,48-;/m0./s1
• InChIKey: ZFUJDXXJCMFOSK-WBUMRSSGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S)-2-[(2R)-2-[(2S)-2-[(2S)-2-(2-{[(2S)-1-[(2S)-1-[(2S)-2-[(2S)-6-amino-2-acetamidohexanamido]-5-carbamimidamidopentanoyl]pyrrolidine-2-carbonyl]pyrrolidin-2-yl]formamido}acetamido)-3-phenylpropanamido]-3-hydroxypropanamido]-3-(naphthalen-2-yl)propanamido]-3-methylpentanoic acid; trifluoroacetic acid
• IUPAC Traditional name: (2S,3S)-2-[(2R)-2-[(2S)-2-[(2S)-2-(2-{[(2S)-1-[(2S)-1-[(2S)-2-[(2S)-6-amino-2-acetamidohexanamido]-5-carbamimidamidopentanoyl]pyrrolidine-2-carbonyl]pyrrolidin-2-yl]formamido}acetamido)-3-phenylpropanamido]-3-hydroxypropanamido]-3-(naphthalen-2-yl)propanamido]-3-methylpentanoic acid; trifluoroacetic acid
• Synonyms: Ac-Lys-[D-betaNal7,lle8]desArg9-bradykinin; R-715 TFA salt

Database IDs

• MDL Number: MFCD16875429
• PubChem SID: 162248767
• PubChem CID: 71311917

CALCULATED PROPERTIES

• Acid pKa: 3.566558
• H Acceptors: 16
• H Donor: 13
• LogD (pH = 5.5): -6.203352
• LogD (pH = 7.4): -5.7781677
• Log P: -3.3639688
• Molar Refractivity: 310.7711 cm^3
• Polarizability: 118.135 Å^3
• Polar Surface Area: 389.77 Å^2
• Rotatable Bonds: 32
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: >1 mg/mL
• Apperance: white to off-white powder

Safety Information

• German water hazard class: 3
• Storage Temperature: -20°C

Product Information

• Purity: ≥95% (HPLC)
• Empirical Formula (Hill Notation): C57H81N13O12 · xC2HF3O2

DETAILS

Sigma Aldrich - R9032

Amino Acid Sequence
Ac-Lys-Arg-Pro-Pro-Gly-Phe-Ser-Ile
Biochem/physiol Actions
Novel, selective, metabolically stable B1 bradykinin receptor antagonist.