(2S)-2-{[(2S,3aS,7aS)-1-[(3R)-2-[(2S)-2-[(2S)-2-(2-{[(2S,4R)-1-[(2S)-1-[(2S)-2-[(2R)-2-amino-5-carbamimidamidopentanamido]-5-carbamimidamidopentanoyl]pyrrolidine-2-carbonyl]-4-hydroxypyrrolidin-2-yl]formamido}acetamido)-3-(thiophen-2-yl)propanamido]-3-hydroxypropanoyl]-1,2,3,4-tetrahydroisoquinoline-3-carbonyl]-octahydro-1H-indol-2-yl]formamido}-5-carbamimidamidopentanoic acid

• ChemBase ID: 155132
• Molecular Formular: C59H89N19O13S
• Molecular Mass: 1304.52246
• Monoisotopic Mass: 1303.660795
• SMILES: c1ccc2c(c1)C[C@@H](N(C2)C(=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](CCCNC(=N)N)N)O)C(=O)N1[C@H]2CCCC[C@H]2C[C@H]1C(=O)N[C@@H](CCCNC(=N)N)C(=O)O
• Canonical SMILES: OC[C@@H](C(=O)N1Cc2ccccc2C[C@@H]1C(=O)N1[C@H]2CCCC[C@H]2C[C@H]1C(=O)N[C@H](C(=O)O)CCCNC(=N)N)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](CCCNC(=N)N)N)CCCNC(=N)N)O
• InChI: InChI=1S/C59H89N19O13S/c60-37(14-5-19-67-57(61)62)48(82)72-38(15-6-20-68-58(63)64)52(86)75-22-8-18-43(75)54(88)77-30-35(80)26-44(77)50(84)70-28-47(81)71-40(27-36-13-9-23-92-36)49(83)74-41(31-79)53(87)76-29-34-12-2-1-10-32(34)24-46(76)55(89)78-42-17-4-3-11-33(42)25-45(78)51(85)73-39(56(90)91)16-7-21-69-59(65)66/h1-2,9-10,12-13,23,33,35,37-46,79-80H,3-8,11,14-22,24-31,60H2,(H,70,84)(H,71,81)(H,72,82)(H,73,85)(H,74,83)(H,90,91)(H4,61,62,67)(H4,63,64,68)(H4,65,66,69)/t33-,35+,37+,38-,39-,40-,41-,42-,43-,44-,45-,46+/m0/s1
• InChIKey: QURWXBZNHXJZBE-SKXRKSCCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-{[(2S,3aS,7aS)-1-[(3R)-2-[(2S)-2-[(2S)-2-(2-{[(2S,4R)-1-[(2S)-1-[(2S)-2-[(2R)-2-amino-5-carbamimidamidopentanamido]-5-carbamimidamidopentanoyl]pyrrolidine-2-carbonyl]-4-hydroxypyrrolidin-2-yl]formamido}acetamido)-3-(thiophen-2-yl)propanamido]-3-hydroxypropanoyl]-1,2,3,4-tetrahydroisoquinoline-3-carbonyl]-octahydro-1H-indol-2-yl]formamido}-5-carbamimidamidopentanoic acid
• IUPAC Traditional name: (2S)-2-{[(2S,3aS,7aS)-1-[(3R)-2-[(2S)-2-[(2S)-2-(2-{[(2S,4R)-1-[(2S)-1-[(2S)-2-[(2R)-2-amino-5-carbamimidamidopentanamido]-5-carbamimidamidopentanoyl]pyrrolidine-2-carbonyl]-4-hydroxypyrrolidin-2-yl]formamido}acetamido)-3-(thiophen-2-yl)propanamido]-3-hydroxypropanoyl]-3,4-dihydro-1H-isoquinoline-3-carbonyl]-octahydroindol-2-yl]formamido}-5-carbamimidamidopentanoic acid
• Synonyms: D-Arg-L-Arg-L-Pro-L-Hyp-Gly-L-(2-thienyl)Ala-L-Ser-D-1,2,3,4-tetrahydro-3-isoquinolinecarbonyl-L-(2α,3β,7aβ)-octahydro-1H-indole-2-carbonyl-L-Arg; Icatibant acetate; HOE 140

Database IDs

• CAS Number: 138614-30-9
• MDL Number: MFCD00213940
• PubChem SID: 162249270
• PubChem CID: 6918173

CALCULATED PROPERTIES

• Acid pKa: 3.4623227
• H Acceptors: 23
• H Donor: 18
• LogD (pH = 5.5): -14.255915
• LogD (pH = 7.4): -12.56894
• Log P: -7.6640034
• Molar Refractivity: 363.7891 cm^3
• Polarizability: 128.73781 Å^3
• Polar Surface Area: 516.22 Å^2
• Rotatable Bonds: 30
• 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: ≥94%
• Empirical Formula (Hill Notation): C59H89N19O13S

DETAILS

Sigma Aldrich - H157

Amino Acid Sequence
Arg-Arg-Pro-Hyp-Gly-Thi-Ser-Tic-Oic-Arg
Biochem/physiol Actions
Selective B2 bradykinin receptor antagonist.