Exendin Fragment 9-39 - Moligand™, ≥95%(HPLC) , Antagonist of GLP-1 receptor, CAS No.133514-43-9, Antagonist of GLP-1 receptor

CAS: 133514-43-9 Cat. No.: E101622 Molecular Weight: 3369.76 PubChem CID: 16198321

GRADE & PURITY Moligand™, ≥95%(HPLC)

Synonyms

Exendin-3 (9-39) | DTXSID00158156 | p | EX-A7432 | Exendin (9-39) | Exendin-3 (9-39) amide | Asp-LEU-SER-LYS-GLN-MET-GLU-GLU-GLU-ALA-VAL-ARG-LEU-PHE-ILE-GLU-TR | AKOS024456934 | ASP-LEU-SER-LYS-GLN-MET-GLU-GLU-GLU-ALA-VAL-ARG-LEU-PHE-ILE-GLU-TRP-LEU-LYS-A

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Amino Acid Sequence Asp-Leu-Ser-Lys-Gln-Met-Glu-Glu-Glu-Ala-Val-Arg-Leu-Phe-Ile-Glu-Trp-Leu-Lys-Asn-Gly-Gly-Pro-Ser-Ser-Gly-Ala-Pro-Pro-Pro-Ser-NH2 Exendin Fragment 9-39 is an antagonist of Glukagon-like peptide-1 (GLP-1) receptor, and also acts as an inhibitor of glucosedependent insulinotropic polypeptide (GIP)-receptor binding. It also prevents the production of cAMP by GIP. GLP-1, along with GIP, acts as a physiological incretin.
Exendin Fragment 9-39 has been used to study its effect on basal microvascular permeability.

Specifications

Synonyms

Exendin-3 (9-39) | DTXSID00158156 | p | EX-A7432 | Exendin (9-39) | Exendin-3 (9-39) amide | Asp-LEU-SER-LYS-GLN-MET-GLU-GLU-GLU-ALA-VAL-ARG-LEU-PHE-ILE-GLU-TR | AKOS024456934 | ASP-LEU-SER-LYS-GLN-MET-GLU-GLU-GLU-ALA-VAL-ARG-LEU-PHE-ILE-GLU-TRP-LEU-LYS-A

Specifications & Purity

Moligand™, ≥95%(HPLC)

Biochemical and Physiological Mechanisms

GLP-1 (Glukagon-like peptide-1) receptor antagonist. Competitive inhibitor of exendin-3 and exendin-4.Potent, selective GLP-1 receptor antagonist (K d = 1.7 nM). Inhibits the generation of intracellular cAMP induced by GLP-1 (7-36), exendin-3 and exendin-

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Action Type

ANTAGONIST

Mechanism of action

Antagonist of GLP-1 receptor

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one week. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥95%(HPLC)

Names and Identifiers

• Canonical Smiles: CCC(C)C(C(=O)NC(CCC(=O)O)C(=O)NC(CC1=CNC2=CC=CC=C21)C(=O)NC(CC(C)C)C(=O)NC(CCCCN)C(=O)NC(CC(=O)N)C(=O)NCC(=O)NCC(=O)N3CCCC3C(=O)NC(CO)C(=O)NC(CO)C(=O)NCC(=O)NC(C)C(=O)N4CCCC4C(=O)N5CCCC5C(=O)N6CCCC6C(=O)NC(CO)C(=O)N)NC(=O)C(CC7=CC=CC=C7)NC(=O)C(CC(C)C)NC(=O)C(CCCNC(=N)N)NC(=O)C(C(C)C)NC(=O)C(C)NC(=O)C(CCC(=O)O)NC(=O)C(CCC(=O)O)NC(=O)C(CCC(=O)O)NC(=O)C(CCSC)NC(=O)C(CCC(=O)N)NC(=O)C(CCCCN)NC(=O)C(CO)NC(=O)C(CC(C)C)NC(=O)C(CC(=O)O)N
• IUPAC Name: (4S)-4-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-5-amino-2-[[(2S)-6-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-amino-3-carboxypropanoyl]amino]-4-methylpentanoyl]amino]-3-hydroxypropanoyl]amino]hexanoyl]amino]-5-oxopentanoyl]amino]-4-methylsulfanylbutanoyl]amino]-4-carboxybutanoyl]amino]-4-carboxybutanoyl]amino]-5-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S,3S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-6-amino-1-[[(2S)-4-amino-1-[[2-[[2-[(2S)-2-[[(2S)-1-[[(2S)-1-[[2-[[(2S)-1-[(2S)-2-[(2S)-2-[(2S)-2-[[(2S)-1-amino-3-hydroxy-1-oxopropan-2-yl]carbamoyl]pyrrolidine-1-carbonyl]pyrrolidine-1-carbonyl]pyrrolidin-1-yl]-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]carbamoyl]pyrrolidin-1-yl]-2-oxoethyl]amino]-2-oxoethyl]amino]-1,4-dioxobutan-2-yl]amino]-1-oxohexan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-4-carboxy-1-oxobutan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-1-oxopropan-2-yl]amino]-5-oxopentanoic acid
• InChIKey: WSEVKKHALHSUMB-MVNVRWBSSA-N
• INCHI: 1S/C149H234N40O47S/c1-14-78(10)120(185-139(227)98(62-81-29-16-15-17-30-81)177-136(224)97(61-76(6)7)175-129(217)88(35-24-53-158-149(156)157)172-144(232)119(77(8)9)184-122(210)79(11)164-126(214)90(41-46-114(199)200)168-131(219)91(42-47-115(201)202)169-132(220)92(43-48-116(203)204)170-134(222)94(50-58-237-13)171-130(218)89(40-45-109(153)194)167-127(215)86(33-20-22-51-150)166-140(228)103(72-192)182-137(225)95(59-74(2)3)174-123(211)84(152)64-118(207)208)145(233)173-93(44-49-117(205)206)133(221)178-99(63-82-66-159-85-32-19-18-31-83(82)85)138(226)176-96(60-75(4)5)135(223)165-87(34-21-23-52-151)128(216)179-100(65-110(154)195)124(212)161-67-111(196)160-69-113(198)186-54-25-36-105(186)142(230)183-104(73-193)141(229)181-102(71-191)125(213)162-68-112(197)163-80(12)146(234)188-56-27-38-107(188)148(236)189-57-28-39-108(189)147(235)187-55-26-37-106(187)143(231)180-101(70-190)121(155)209/h15-19,29-32,66,74-80,84,86-108,119-120,159,190-193H,14,20-28,33-65,67-73,150-152H2,1-13H3,(H2,153,194)(H2,154,195)(H2,155,209)(H,160,196)(H,161,212)(H,162,213)(H,163,197)(H,164,214)(H,165,223)(H,166,228)(H,167,215)(H,168,219)(H,169,220)(H,170,222)(H,171,218)(H,172,232)(H,173,233)(H,174,211)(H,175,217)(H,176,226)(H,177,224)(H,178,221)(H,179,216)(H,180,231)(H,181,229)(H,182,225)(H,183,230)(H,184,210)(H,185,227)(H,199,200)(H,201,202)(H,203,204)(H,205,206)(H,207,208)(H4,156,157,158)/t78-,79-,80-,84-,86-,87-,88-,89-,90-,91-,92-,93-,94-,95-,96-,97-,98-,99-,100-,101-,102-,103-,104-,105-,106-,107-,108-,119-,120-/m0/s1
• Isomeric SMILES: CC[C@H](C)[C@@H](C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CC1=CNC2=CC=CC=C21)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(=O)N)C(=O)NCC(=O)NCC(=O)N3CCC[C@H]3C(=O)N[C@@H](CO)C(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H](C)C(=O)N4CCC[C@H]4C(=O)N5CCC[C@H]5C(=O)N6CCC[C@H]6C(=O)N[C@@H](CO)C(=O)N)NC(=O)[C@H](CC7=CC=CC=C7)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](C(C)C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CCSC)NC(=O)[C@H](CCC(=O)N)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(=O)O)N
• WGK Germany: 3
• PubChem CID: 16198321
• Molecular Weight: 3369.76

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic Polymers
    • Class Polypeptides

• Kingdom: Organic compounds
• Superclass: Organic Polymers
• Class: Polypeptides
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Polypeptides
• Alternative Parents: Peptides Phenylalanine and derivatives Arginine and derivatives Pentacarboxylic acids and derivatives Glutamine and derivatives Glutamic acid and derivatives Methionine and derivatives Asparagine and derivatives Isoleucine and derivatives Aspartic acid and derivatives Leucine and derivatives Proline and derivatives Valine and derivatives N-acyl-alpha amino acids and derivatives Tryptamines and derivatives Alpha amino acid amides Serine and derivatives Alanine and derivatives 3-alkylindoles Amphetamines and derivatives N-acylpyrrolidines Pyrrolidinecarboxamides Substituted pyrroles N-acyl amines Tertiary carboxylic acid amides Heteroaromatic compounds Primary carboxylic acid amides Guanidines Secondary carboxylic acid amides Amino acids Sulfenyl compounds Dialkylthioethers Carboxylic acids Azacyclic compounds Carboximidamides Hydrocarbon derivatives Primary alcohols Organic oxides Monoalkylamines Carbonyl compounds Imines
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Polypeptide - Alpha peptide - Arginine or derivatives - Phenylalanine or derivatives - Pentacarboxylic acid or derivatives - Glutamic acid or derivatives - Glutamine or derivatives - Methionine or derivatives - Asparagine or derivatives - Aspartic acid or derivatives - Isoleucine or derivatives - Leucine or derivatives - Valine or derivatives - Proline or derivatives - N-acyl-alpha amino acid or derivatives - Alpha-amino acid amide - Serine or derivatives - Triptan - Alanine or derivatives - Amphetamine or derivatives - N-substituted-alpha-amino acid - 3-alkylindole - Alpha-amino acid or derivatives - Indole - Indole or derivatives - Pyrrolidine carboxylic acid or derivatives - Pyrrolidine-2-carboxamide - N-acylpyrrolidine - Benzenoid - Substituted pyrrole - N-acyl-amine - Fatty acyl - Fatty amide - Monocyclic benzene moiety - Heteroaromatic compound - Tertiary carboxylic acid amide - Pyrrole - Pyrrolidine - Secondary carboxylic acid amide - Primary carboxylic acid amide - Amino acid or derivatives - Amino acid - Carboxamide group - Guanidine - Thioether - Carboxylic acid derivative - Carboxylic acid - Azacycle - Organoheterocyclic compound - Dialkylthioether - Sulfenyl compound - Carboximidamide - Organooxygen compound - Alcohol - Organic oxygen compound - Primary amine - Organosulfur compound - Carbonyl group - Hydrocarbon derivative - Imine - Primary alcohol - Amine - Primary aliphatic amine - Organic nitrogen compound - Organic oxide - Organonitrogen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as polypeptides. These are peptides containing ten or more amino acid residues.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

GLP1R Tclin Glucagon-like peptide 1 receptor (0 Activities)

Discover Target: GLP1R

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

Mechanisms of Action

Chemical and Physical Properties

• Molecular Weight: 3369.800 g/mol
• XLogP3: -16.700
• Hydrogen Bond Donor Count: 45
• Hydrogen Bond Acceptor Count: 52
• Rotatable Bond Count: 109
• Exact Mass: 3368.69 Da
• Monoisotopic Mass: 3367.69 Da
• Topological Polar Surface Area: 1420.000 Ų
• Heavy Atom Count: 237
• Formal Charge: 0
• Complexity: 8000.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 29
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Zhang Jian-Mei, Sun Yin-Shuang, Zhao Li-Qin, Chen Tian-Tian, Fan Mei-Na, Jiao Hong-Chao, Zhao Jing-Peng, Wang Xiao-Juan, Li Fu-Chang, Li Hai-Fang, Lin Hai.  (2019)  SCFAs-Induced GLP-1 Secretion Links the Regulation of Gut Microbiome on Hepatic Lipogenesis in Chickens.  Frontiers in Microbiology,      [PMID:31616396] [10.3389/fmicb.2019.02176]

2. GengShan , YangShan , TangXuejiao , XueShiyao , LiKe , LiuDongfang , ChenChen , ZhuZhiming , ZhengHongting , WangYuanqiang , YangGangyi , LiLing , YangMengliu.  (2024)  Intestinal NUCB2/nesfatin-1 regulates hepatic glucose production via the MC4R-cAMP-GLP-1 pathway.  EMBO JOURNAL,      [PMID:39562740] [10.1038/s44318-024-00300-4]