icatibant   Click here for help

GtoPdb Ligand ID: 667

Synonyms: D-Arg-[Hyp3,Thi5,D-Tic7,Oic8]BK | Firazyr® | HOE 140 | HOE140
Approved drug Immunopharmacology Ligand
icatibant is an approved drug (EMA (2008), FDA (2011))
Comment: Synthetic analogue of bradykinin. There is some ambiguity in the literature and on online resources as to the exact chemical structure and stereochemistry of icatibant.
The HELM annotation is PEPTIDE1{[dR].(R,[dR]).(P,[dP]).[*C(=O)C1C[C@H](CN1*)O |$_R2;;;;;;;;_R1;$|].G.[Thi].S.[*C(=O)C1Cc2ccccc2CN1* |$_R2;;;;;;;;;;;;;_R1$|].[*C(=O)C1C[C@@H]2CCCC[C@@H]2N1* |$_R2;;;;;;;;;;;;_R1$|].R}$$$$V2.0 (from PubChem).
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2D Structure
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SMILES / InChI / InChIKey
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Canonical SMILES OC[C@@H](C(=O)N1Cc2ccccc2CC1C(=O)N1[C@H]2CCCC[C@H]2CC1C(=O)N[C@H](C(=O)O)CCCN=C(N)N)NC(=O)[C@H](Cc1cccs1)NC(=O)CNC(=O)C1C[C@H](CN1C(=O)C1CCCN1C(=O)C(NC(=O)[C@@H](CCCN=C(N)N)N)CCCN=C(N)N)O
Isomeric SMILES OC[C@@H](C(=O)N1Cc2ccccc2CC1C(=O)N1[C@H]2CCCC[C@H]2CC1C(=O)N[C@H](C(=O)O)CCCN=C(N)N)NC(=O)[C@H](Cc1cccs1)NC(=O)CNC(=O)C1C[C@H](CN1C(=O)C1CCCN1C(=O)C(NC(=O)[C@@H](CCCN=C(N)N)N)CCCN=C(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
InChI Key QURWXBZNHXJZBE-MCDGZUPGSA-N

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