Glucagon like peptide-1(GLP-1)

ID: ALA428139

Chembl Id: CHEMBL428139

PubChem CID: 44290899

Max Phase: Preclinical

Molecular Formula: C151H228N40O47

Molecular Weight: 3355.72

Molecule Type: Protein

Names and Identifiers

Canonical SMILES:  CC[C@H](C)[C@H](NC(=O)[C@H](Cc1ccccc1)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(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)Cc1c[nH]cn1)[C@@H](C)O)[C@@H](C)O)C(C)C)C(=O)N[C@@H](C)C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](CCCN=C(N)N)C(=O)NCC(=O)O)C(C)C

Standard InChI:  InChI=1S/C151H228N40O47/c1-17-77(10)121(148(236)169-81(14)127(215)177-105(60-87-63-160-92-36-25-24-35-90(87)92)138(226)179-101(56-74(4)5)139(227)188-119(75(6)7)146(234)176-94(37-26-28-52-152)130(218)161-65-111(199)170-93(39-30-54-159-151(156)157)129(217)164-68-118(210)211)190-140(228)103(57-84-31-20-18-21-32-84)180-135(223)99(47-51-116(206)207)175-134(222)95(38-27-29-53-153)172-125(213)79(12)166-124(212)78(11)168-133(221)98(44-48-110(155)198)171-112(200)66-162-132(220)97(46-50-115(204)205)174-136(224)100(55-73(2)3)178-137(225)102(59-86-40-42-89(197)43-41-86)181-143(231)107(69-192)184-145(233)109(71-194)185-147(235)120(76(8)9)189-142(230)106(62-117(208)209)182-144(232)108(70-193)186-150(238)123(83(16)196)191-141(229)104(58-85-33-22-19-23-34-85)183-149(237)122(82(15)195)187-113(201)67-163-131(219)96(45-49-114(202)203)173-126(214)80(13)167-128(216)91(154)61-88-64-158-72-165-88/h18-25,31-36,40-43,63-64,72-83,91,93-109,119-123,160,192-197H,17,26-30,37-39,44-62,65-71,152-154H2,1-16H3,(H2,155,198)(H,158,165)(H,161,218)(H,162,220)(H,163,219)(H,164,217)(H,166,212)(H,167,216)(H,168,221)(H,169,236)(H,170,199)(H,171,200)(H,172,213)(H,173,214)(H,174,224)(H,175,222)(H,176,234)(H,177,215)(H,178,225)(H,179,226)(H,180,223)(H,181,231)(H,182,232)(H,183,237)(H,184,233)(H,185,235)(H,186,238)(H,187,201)(H,188,227)(H,189,230)(H,190,228)(H,191,229)(H,202,203)(H,204,205)(H,206,207)(H,208,209)(H,210,211)(H4,156,157,159)/t77-,78-,79-,80-,81-,82+,83+,91-,93-,94-,95-,96-,97-,98-,99-,100-,101-,102-,103-,104-,105-,106-,107-,108-,109-,119-,120-,121-,122-,123-/m0/s1

Standard InChI Key:  GCYXWQUSHADNBF-AAEALURTSA-N

Alternative Forms

1. Parent:

   

   ALA428139

   Glucagon-like peptide 1-(7-37)

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Protein

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 3355.72

Molecular Weight (Monoisotopic): 3353.6681

AlogP: ┄

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HBA: ┄

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HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: ┄

CX LogD: ┄

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Np Likeness Score: ┄

References

1. Knudsen LB, Nielsen PF, Huusfeldt PO, Johansen NL, Madsen K, Pedersen FZ, Thøgersen H, Wilken M, Agersø H..  (2000)  Potent derivatives of glucagon-like peptide-1 with pharmacokinetic properties suitable for once daily administration.,  43  (9): [PMID:10794683] [10.1021/jm9909645]

2. Knudsen LB, Kiel D, Teng M, Behrens C, Bhumralkar D, Kodra JT, Holst JJ, Jeppesen CB, Johnson MD, de Jong JC, Jorgensen AS, Kercher T, Kostrowicki J, Madsen P, Olesen PH, Petersen JS, Poulsen F, Sidelmann UG, Sturis J, Truesdale L, May J, Lau J..  (2007)  Small-molecule agonists for the glucagon-like peptide 1 receptor.,  104  (3): [PMID:17213325] [10.1073/pnas.0605701104]

3. Giordanetto F, Revell JD, Knerr L, Hostettler M, Paunovic A, Priest C, Janefeldt A, Gill A..  (2013)  Stapled Vasoactive Intestinal Peptide (VIP) Derivatives Improve VPAC2 Agonism and Glucose-Dependent Insulin Secretion.,  4  (12): [PMID:24900623] [10.1021/ml400257h]

4. Lau J, Bloch P, Schäffer L, Pettersson I, Spetzler J, Kofoed J, Madsen K, Knudsen LB, McGuire J, Steensgaard DB, Strauss HM, Gram DX, Knudsen SM, Nielsen FS, Thygesen P, Reedtz-Runge S, Kruse T..  (2015)  Discovery of the Once-Weekly Glucagon-Like Peptide-1 (GLP-1) Analogue Semaglutide.,  58  (18): [PMID:26308095] [10.1021/acs.jmedchem.5b00726]

5. Zhou J, Cai X, Huang X, Dai Y, Sun L, Zhang B, Yang B, Lin H, Huang W, Qian H..  (2017)  A novel glucagon-like peptide-1/glucagon receptor dual agonist exhibits weight-lowering and diabetes-protective effects.,  138  [PMID:28772236] [10.1016/j.ejmech.2017.07.046]

6. Østergaard S, Kofoed J, Paulsson JF, Madsen KG, Jorgensen R, Wulff BS..  (2018)  Design of Y2 Receptor Selective and Proteolytically Stable PYY3-36 Analogues.,  61  (23): [PMID:30399314] [10.1021/acs.jmedchem.8b01046]

7. Kobayashi D, Kuraoka E, Hayashi J, Yasuda T, Kohmura Y, Denda M, Harada N, Inagaki N, Otaka A..  (2022)  S-Protected Cysteine Sulfoxide-Enabled Tryptophan-Selective Modification with Application to Peptide Lipidation.,  13  (7.0): [PMID:35859873] [10.1021/acsmedchemlett.2c00161]

Source

Source(1):

• Scientific Literature