(2S)-5-carbamimidamido-2-[(2S)-2-[(2R)-2-[(2S)-2-[(2S)-2-(2-{[(2S,4R)-1-[(2S)-1-[(2S)-5-carbamimidamido-2-[(2R)-5-carbamimidamido-2-{2-[(3R,5S,7s)-adamantan-1-yl]acetamido}pentanamido]pentanoyl]pyrrolidine-2-carbonyl]-4-hydroxypyrrolidin-2-yl]formamido}acetamido)-3-(thiophen-2-yl)propanamido]-3-hydroxypropanamido]-3-phenylpropanamido]-3-(thiophen-2-yl)propanamido]pentanoic acid

• ChemBase ID: 131012
• Molecular Formular: C68H99N19O14S2
• Molecular Mass: 1470.76256
• Monoisotopic Mass: 1469.70603094
• SMILES: c1ccc(cc1)C[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)CNC(=O)[C@H]1N(C[C@@H](C1)O)C(=O)[C@H]1N(CCC1)C(=O)[C@@H](NC(=O)[C@H](NC(=O)C[C@@]12C[C@H]3C[C@H](C1)C[C@@H](C2)C3)CCCNC(=N)N)CCCNC(=N)N)Cc1sccc1)CO)C(=O)N[C@H](C(=O)N[C@H](C(=O)O)CCCNC(=N)N)Cc1sccc1
• Canonical SMILES: OC[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)NC(=O)[C@H](Cc1cccs1)NC(=O)CNC(=O)[C@@H]1C[C@H](CN1C(=O)[C@@H]1CCCN1C(=O)[C@@H](NC(=O)[C@H](NC(=O)C[C@]12C[C@@H]3C[C@@H](C2)C[C@@H](C1)C3)CCCNC(=N)N)CCCNC(=N)N)O
• InChI: InChI=1S/C68H99N19O14S2/c69-65(70)75-18-4-14-45(79-54(90)34-68-31-39-24-40(32-68)26-41(25-39)33-68)56(92)81-46(15-5-19-76-66(71)72)62(98)86-21-7-17-52(86)63(99)87-36-42(89)28-53(87)61(97)78-35-55(91)80-49(29-43-12-8-22-102-43)58(94)85-51(37-88)60(96)83-48(27-38-10-2-1-3-11-38)57(93)84-50(30-44-13-9-23-103-44)59(95)82-47(64(100)101)16-6-20-77-67(73)74/h1-3,8-13,22-23,39-42,45-53,88-89H,4-7,14-21,24-37H2,(H,78,97)(H,79,90)(H,80,91)(H,81,92)(H,82,95)(H,83,96)(H,84,93)(H,85,94)(H,100,101)(H4,69,70,75)(H4,71,72,76)(H4,73,74,77)/t39-,40+,41-,42-,45-,46+,47+,48-,49+,50+,51+,52+,53+,68-/m1/s1
• InChIKey: LTDPOXAWOYRJKV-ATTXSSDWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-5-carbamimidamido-2-[(2S)-2-[(2R)-2-[(2S)-2-[(2S)-2-(2-{[(2S,4R)-1-[(2S)-1-[(2S)-5-carbamimidamido-2-[(2R)-5-carbamimidamido-2-{2-[(3R,5S,7s)-adamantan-1-yl]acetamido}pentanamido]pentanoyl]pyrrolidine-2-carbonyl]-4-hydroxypyrrolidin-2-yl]formamido}acetamido)-3-(thiophen-2-yl)propanamido]-3-hydroxypropanamido]-3-phenylpropanamido]-3-(thiophen-2-yl)propanamido]pentanoic acid
• IUPAC Traditional name: (2S)-5-carbamimidamido-2-[(2S)-2-[(2R)-2-[(2S)-2-[(2S)-2-(2-{[(2S,4R)-1-[(2S)-1-[(2S)-5-carbamimidamido-2-[(2R)-5-carbamimidamido-2-{2-[(3R,5S,7s)-adamantan-1-yl]acetamido}pentanamido]pentanoyl]pyrrolidine-2-carbonyl]-4-hydroxypyrrolidin-2-yl]formamido}acetamido)-3-(thiophen-2-yl)propanamido]-3-hydroxypropanamido]-3-phenylpropanamido]-3-(thiophen-2-yl)propanamido]pentanoic acid
• Synonyms: Nα-Adamantaneacetyl-D-Arg-[Hyp3, Thi5,8, D-Phe7]-Bradykinin

Database IDs

• CAS Number: 130942-96-0
• MDL Number: MFCD00142579
• PubChem SID: 162225290
• PubChem CID: 57357447

CALCULATED PROPERTIES

• Acid pKa: -1.4145067
• H Acceptors: 23
• H Donor: 20
• LogD (pH = 5.5): -9.691711
• LogD (pH = 7.4): -9.673212
• Log P: -5.580055
• Molar Refractivity: 407.7924 cm^3
• Polarizability: 145.88205 Å^3
• Polar Surface Area: 536.88 Å^2
• Rotatable Bonds: 39
• 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

Pharmacology Properties

• Gene Information: human ... BDKRB2(624)mouse ... BDKRB2(12062)rat ... BDKRB2(25245)

Product Information

• Purity: ≥97% (HPLC)

DETAILS

Sigma Aldrich - B6029

Amino Acid Sequence
Nα-Adamantaneacetyl-D-Arg-Arg-Pro-Hydroxy-Pro-Gly-β-(2-Thienyl)Ala-Ser-D-Phe-β-(2-Thienyl)Ala-Arg
Biochem/physiol Actions
A highly potent antagonist at bradykinin B2 receptors with no agonist activity.