taspoglutide   Click here for help

GtoPdb Ligand ID: 13315

Synonyms: BIM51077 | ITM077 | R1583
Compound class: Peptide
Comment: Taspoglutide is a long-acting peptidic GLP-1 receptor agonist, with alpha-aminoisobutyric acid substitutions replacing the Ala8 and Gly35 residues of the endogenous hGLP-1(7-36)NH2 peptide [1-2]. It is resistant to protelytic cleavage by dipeptidyl peptidase-4.
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2D Structure
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SMILES / InChI / InChIKey
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Canonical SMILES CC[C@H](C)[C@@H](C(=O)N[C@@H](C)C(=O)N[C@@H](CC1=CNC2=C1C=CC=C2)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)NC(C)(C)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N)NC(=O)[C@H](CC3=CC=CC=C3)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(=O)N)NC(=O)CNC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC4=CC=C(C=C4)O)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](CO)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CC5=CC=CC=C5)NC(=O)[C@H]([C@@H](C)O)NC(=O)CNC(=O)[C@H](CCC(=O)O)NC(=O)C(C)(C)NC(=O)[C@H](CC6=CN=CN6)N
Isomeric SMILES CC[C@H](C)[C@@H](C(=O)N[C@@H](C)C(=O)N[C@@H](CC1=CNC2=CC=CC=C21)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)NC(C)(C)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N)NC(=O)[C@H](CC3=CC=CC=C3)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(=O)N)NC(=O)CNC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC4=CC=C(C=C4)O)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](CO)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CC5=CC=CC=C5)NC(=O)[C@H]([C@@H](C)O)NC(=O)CNC(=O)[C@H](CCC(=O)O)NC(=O)C(C)(C)NC(=O)[C@H](CC6=CN=CN6)N
InChI InChI=1S/C152H232N40O45/c1-20-78(10)119(145(233)168-81(13)125(213)174-105(63-87-66-162-92-39-28-27-38-90(87)92)134(222)176-101(59-75(4)5)135(223)187-117(76(6)7)143(231)173-95(41-30-32-56-154)142(230)192-152(18,19)148(236)184-93(122(157)210)42-33-57-161-150(158)159)189-136(224)103(60-84-34-23-21-24-35-84)177-131(219)99(50-54-115(206)207)172-130(218)94(40-29-31-55-153)170-124(212)80(12)166-123(211)79(11)167-129(217)98(47-51-110(156)199)169-111(200)68-163-127(215)96(48-52-113(202)203)171-132(220)100(58-74(2)3)175-133(221)102(62-86-43-45-89(198)46-44-86)178-139(227)107(70-193)181-141(229)109(72-195)182-144(232)118(77(8)9)188-138(226)106(65-116(208)209)179-140(228)108(71-194)183-147(235)121(83(15)197)190-137(225)104(61-85-36-25-22-26-37-85)180-146(234)120(82(14)196)186-112(201)69-164-128(216)97(49-53-114(204)205)185-149(237)151(16,17)191-126(214)91(155)64-88-67-160-73-165-88/h21-28,34-39,43-46,66-67,73-83,91,93-109,117-121,162,193-198H,20,29-33,40-42,47-65,68-72,153-155H2,1-19H3,(H2,156,199)(H2,157,210)(H,160,165)(H,163,215)(H,164,216)(H,166,211)(H,167,217)(H,168,233)(H,169,200)(H,170,212)(H,171,220)(H,172,218)(H,173,231)(H,174,213)(H,175,221)(H,176,222)(H,177,219)(H,178,227)(H,179,228)(H,180,234)(H,181,229)(H,182,232)(H,183,235)(H,184,236)(H,185,237)(H,186,201)(H,187,223)(H,188,226)(H,189,224)(H,190,225)(H,191,214)(H,192,230)(H,202,203)(H,204,205)(H,206,207)(H,208,209)(H4,158,159,161)/t78-,79-,80-,81-,82+,83+,91-,93-,94-,95-,96-,97-,98-,99-,100-,101-,102-,103-,104-,105-,106-,107-,108-,109-,117-,118-,119-,120-,121-/m0/s1
InChI Key WRGVLTAWMNZWGT-VQSPYGJZSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

Classification Click here for help
Compound class Peptide
International Nonproprietary Names Click here for help
INN number INN
8975 taspoglutide
Synonyms Click here for help
BIM51077 | ITM077 | R1583
Database Links Click here for help
Specialist databases
GPCRdb Ligand taspoglutide
Other databases
DrugBank Ligand DB14027
GtoPdb PubChem SID 496703285
PubChem CID 56842233
Search Google for chemical match using the InChIKey WRGVLTAWMNZWGT-VQSPYGJZSA-N
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UniChem Compound Search for chemical match using the InChIKey WRGVLTAWMNZWGT-VQSPYGJZSA-N
UniChem Connectivity Search for chemical match using the InChIKey WRGVLTAWMNZWGT-VQSPYGJZSA-N

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MedChemExpress
Taspoglutide (links to external site)
Cat. No. HY-P0165