liraglutide (CHEBI:71193)

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CHEBI:71193 - liraglutide

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ChEBI ID	CHEBI:71193
ChEBI Name	liraglutide
Stars
Definition	A lipopeptide that is an analogue of human GLP-1 in which the lysine residue at position 27 is replaced by arginine and a hexadecanoyl group attached to the remaining lysine via a glutamic acid spacer. Used as an adjunct to diet and exercise to improve glycemic control in adults with type 2 diabetes mellitus.
Last Modified	22 February 2017
Submitter	Steve
Downloads	Molfile

Formula	C172H265N43O51
Net Charge	0
Average Mass	3751.262
Monoisotopic Mass	3748.94646
SMILES	CCCCCCCCCCCCCCCC(=O)N[C@@H](CCC(=O)NCCCC[C@H](NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(N)=O)NC(=O)CNC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](C)NC(=O)[C@@H](N)Cc1cncn1)[C@@H](C)O)[C@@H](C)O)C(C)C)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@H](C(=O)N[C@@H](C)C(=O)N[C@@H](Cc1cnc2ccccc12)C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](C(=O)N[C@@H](CCCNC(=N)N)C(=O)NCC(=O)N[C@@H](CCCNC(=N)N)C(=O)NCC(=O)O)C(C)C)[C@@H](C)CC)C(=O)O
InChI	InChI=1S/C172H265N43O51/c1-18-20-21-22-23-24-25-26-27-28-29-30-37-53-129(224)195-116(170(265)266)59-64-128(223)180-68-41-40-50-111(153(248)199-115(62-67-135(232)233)154(249)204-120(73-100-44-33-31-34-45-100)159(254)214-140(93(11)19-2)167(262)192-97(15)146(241)201-122(76-103-79-183-108-49-39-38-48-106(103)108)157(252)203-118(72-90(5)6)158(253)212-138(91(7)8)165(260)200-110(52-43-70-182-172(177)178)149(244)184-81-130(225)193-109(51-42-69-181-171(175)176)148(243)187-84-137(236)237)196-144(239)95(13)189-143(238)94(12)191-152(247)114(58-63-127(174)222)194-131(226)82-185-151(246)113(61-66-134(230)231)198-155(250)117(71-89(3)4)202-156(251)119(75-102-54-56-105(221)57-55-102)205-162(257)124(85-216)208-164(259)126(87-218)209-166(261)139(92(9)10)213-161(256)123(78-136(234)235)206-163(258)125(86-217)210-169(264)142(99(17)220)215-160(255)121(74-101-46-35-32-36-47-101)207-168(263)141(98(16)219)211-132(227)83-186-150(245)112(60-65-133(228)229)197-145(240)96(14)190-147(242)107(173)77-104-80-179-88-188-104/h31-36,38-39,44-49,54-57,79-80,88-99,107,109-126,138-142,183,216-221H,18-30,37,40-43,50-53,58-78,81-87,173H2,1-17H3,(H2,174,222)(H,179,188)(H,180,223)(H,184,244)(H,185,246)(H,186,245)(H,187,243)(H,189,238)(H,190,242)(H,191,247)(H,192,262)(H,193,225)(H,194,226)(H,195,224)(H,196,239)(H,197,240)(H,198,250)(H,199,248)(H,200,260)(H,201,241)(H,202,251)(H,203,252)(H,204,249)(H,205,257)(H,206,258)(H,207,263)(H,208,259)(H,209,261)(H,210,264)(H,211,227)(H,212,253)(H,213,256)(H,214,254)(H,215,255)(H,228,229)(H,230,231)(H,232,233)(H,234,235)(H,236,237)(H,265,266)(H4,175,176,181)(H4,177,178,182)/t93-,94-,95-,96-,97-,98+,99+,107-,109-,110-,111-,112-,113-,114-,115-,116-,117-,118-,119-,120-,121-,122-,123-,124-,125-,126-,138-,139-,140-,141-,142-/m0/s1
InChIKey	YSDQQAXHVYUZIW-QCIJIYAXSA-N

Wikipedia

Roles Classification

Chemical Role:	Bronsted base A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:	anti-obesity agent Any substance which is used to reduce or control weight. glucagon-like peptide-1 receptor agonist An agonist that binds to and activates glucagon-like peptide-1 (GLP-1) receptors.
Applications:	cardiovascular drug A drug that affects the rate or intensity of cardiac contraction, blood vessel diameter or blood volume. hypoglycemic agent A drug which lowers the blood glucose level. antiparkinson drug A drug used in the treatment of Parkinson's disease. antipsychotic agent Antipsychotic drugs are agents that control agitated psychotic behaviour, alleviate acute psychotic states, reduce psychotic symptoms, and exert a quieting effect. antidepressant Antidepressants are mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions. neuroprotective agent Any compound that can be used for the treatment of neurodegenerative disorders.

ChEBI Ontology

Outgoing Relation(s)
	liraglutide (CHEBI:71193) has role anti-obesity agent (CHEBI:74518)
	liraglutide (CHEBI:71193) has role antidepressant (CHEBI:35469)
	liraglutide (CHEBI:71193) has role antiparkinson drug (CHEBI:48407)
	liraglutide (CHEBI:71193) has role antipsychotic agent (CHEBI:35476)
	liraglutide (CHEBI:71193) has role cardiovascular drug (CHEBI:35554)
	liraglutide (CHEBI:71193) has role glucagon-like peptide-1 receptor agonist (CHEBI:71196)
	liraglutide (CHEBI:71193) has role hypoglycemic agent (CHEBI:35526)
	liraglutide (CHEBI:71193) has role neuroprotective agent (CHEBI:63726)
	liraglutide (CHEBI:71193) is a lipopeptide (CHEBI:46895)
	liraglutide (CHEBI:71193) is a organic molecular entity (CHEBI:50860)
	liraglutide (CHEBI:71193) is a polypeptide (CHEBI:15841)

IUPAC Name
N2-(L-histidyl-L-alanyl-L-α-glutamylglycyl-L-threonyl-L-phenylalanyl-L-threonyl-L-seryl-L-α-aspartyl-L-valyl-L-seryl-L-seryl-L-tyrosyl-L-leucyl-L-α-glutamylglycyl-L-glutaminyl-L-alanyl-L-alanyl)-N⁶-(N-hexadecanoyl-L-γ-glutamyl)-L-lysyl-L-α-glutamyl-L-phenylalanyl-L-isoleucyl-L-alanyl-L-tryptophyl-L-leucyl-L-valyl-L-arginylglycyl-L-arginylglycine

INNs	Source
liraglutida	ChemIDplus
liraglutide	WHO MedNet
liraglutide	KEGG DRUG
liraglutidum	ChemIDplus

Synonyms	Source
Liraglutide (rdna origin)	ChEMBL
NN 2211	ChemIDplus
NN-2211	ChemIDplus
NN2211	ChemIDplus
NN-9924	ChEMBL
NN9924	ChEMBL

Brand Names	Source
Liraglutide component of xultophy 100/3.6	ChEMBL
Victoza	KEGG DRUG

Manual Xrefs	Databases
4164	DrugCentral
D06404	KEGG DRUG
DB06655	DrugBank
Liraglutide	Wikipedia
US2006160736	Patent
WO2008011518	Patent

Registry Numbers	Sources
Reaxys:10331362	Reaxys
CAS:204656-20-2	KEGG DRUG
CAS:204656-20-2	ChemIDplus

Citations