structure of CID 90488736

CID 90488736

CAS No.: 100040-31-1
M. Wt: 4983.53
M. Fa: C226H338N60O66S
InChI Key: MGXWVYUBJRZYPE-YUGYIWNOSA-N
Appearance: White to Off-White Solid

Names and Identifiers of CID 90488736

CAS Number

100040-31-1

IUPAC Name

(2S)-5-amino-2-[[(2S,3R)-2-[[(2S,3S)-2-[[(2S)-4-amino-2-[[(2S)-2-[[(2S)-6-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-4-amino-2-[[(2S)-6-amino-2-[[(2S)-6-amino-2-[[2-[[(2S)-6-amino-2-[[(2S)-5-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-4-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-5-amino-2-[[(2S)-5-amino-2-[[(2S)-2-[[(2S,3S)-2-[[(2S)-6-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S,3S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S,3S)-2-[[(2S)-2-[[(2S,3R)-2-[[2-[[(2S)-2-[[(2S)-2-[[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]propanoyl]amino]-4-carboxybutanoyl]amino]acetyl]amino]-3-hydroxybutanoyl]amino]-3-phenylpropanoyl]amino]-3-methylpentanoyl]amino]-3-hydroxypropanoyl]amino]-3-carboxypropanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-3-hydroxypropanoyl]amino]-3-methylpentanoyl]amino]propanoyl]amino]-4-methylsulfanylbutanoyl]amino]-3-carboxypropanoyl]amino]hexanoyl]amino]-3-methylpentanoyl]amino]-3-(1H-imidazol-4-yl)propanoyl]amino]-5-oxopentanoyl]amino]-5-oxopentanoyl]amino]-3-carboxypropanoyl]amino]-3-phenylpropanoyl]amino]-3-methylbutanoyl]amino]-4-oxobutanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-4-methylpentanoyl]amino]-4-methylpentanoyl]amino]propanoyl]amino]-5-oxopentanoyl]amino]hexanoyl]amino]acetyl]amino]hexanoyl]amino]hexanoyl]amino]-4-oxobutanoyl]amino]-3-carboxypropanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]hexanoyl]amino]-3-(1H-imidazol-4-yl)propanoyl]amino]-4-oxobutanoyl]amino]-3-methylpentanoyl]amino]-3-hydroxybutanoyl]amino]-5-oxopentanoic acid

InChI

InChI=1S/C226H338N60O66S/c1-21-113(11)181(285-218(343)165(107-288)278-203(328)150(88-125-60-64-131(292)65-61-125)264-212(337)163(99-179(310)311)274-217(342)164(106-287)279-222(347)183(115(13)23-3)283-215(340)152(87-123-47-29-26-30-48-123)275-224(349)185(120(18)289)280-174(301)105-245-192(317)142(70-75-175(302)303)252-187(312)117(15)248-190(315)134(232)85-124-58-62-130(291)63-59-124)220(345)250-119(17)189(314)254-146(76-82-353-20)199(324)272-160(96-176(304)305)210(335)258-141(57-39-44-81-231)200(325)282-182(114(12)22-2)221(346)276-156(92-129-103-241-109-247-129)206(331)260-144(67-72-167(234)294)197(322)259-145(68-73-168(235)295)198(323)271-161(97-177(306)307)211(336)265-151(86-122-45-27-25-28-46-122)214(339)281-180(112(9)10)219(344)277-158(94-171(238)298)209(334)266-154(90-127-101-243-136-52-34-32-50-133(127)136)205(330)263-149(84-111(7)8)202(327)262-148(83-110(5)6)201(326)249-118(16)188(313)253-143(66-71-166(233)293)196(321)255-137(53-35-40-77-227)191(316)244-104-173(300)251-138(54-36-41-78-228)193(318)256-139(55-37-42-79-229)195(320)269-157(93-170(237)297)208(333)273-162(98-178(308)309)213(338)267-153(89-126-100-242-135-51-33-31-49-132(126)135)204(329)257-140(56-38-43-80-230)194(319)268-155(91-128-102-240-108-246-128)207(332)270-159(95-172(239)299)216(341)284-184(116(14)24-4)223(348)286-186(121(19)290)225(350)261-147(226(351)352)69-74-169(236)296/h25-34,45-52,58-65,100-103,108-121,134,137-165,180-186,242-243,287-292H,21-24,35-44,53-57,66-99,104-107,227-232H2,1-20H3,(H2,233,293)(H2,234,294)(H2,235,295)(H2,236,296)(H2,237,297)(H2,238,298)(H2,239,299)(H,240,246)(H,241,247)(H,244,316)(H,245,317)(H,248,315)(H,249,326)(H,250,345)(H,251,300)(H,252,312)(H,253,313)(H,254,314)(H,255,321)(H,256,318)(H,257,329)(H,258,335)(H,259,322)(H,260,331)(H,261,350)(H,262,327)(H,263,330)(H,264,337)(H,265,336)(H,266,334)(H,267,338)(H,268,319)(H,269,320)(H,270,332)(H,271,323)(H,272,324)(H,273,333)(H,274,342)(H,275,349)(H,276,346)(H,277,344)(H,278,328)(H,279,347)(H,280,301)(H,281,339)(H,282,325)(H,283,340)(H,284,341)(H,285,343)(H,286,348)(H,302,303)(H,304,305)(H,306,307)(H,308,309)(H,310,311)(H,351,352)/t113-,114-,115-,116-,117-,118-,119-,120+,121+,134-,137-,138-,139-,140-,141-,142-,143-,144-,145-,146-,147-,148-,149-,150-,151-,152-,153-,154-,155-,156-,157-,158-,159-,160-,161-,162-,163-,164-,165-,180-,181-,182-,183-,184-,185-,186-/m0/s1

InChIKey

MGXWVYUBJRZYPE-YUGYIWNOSA-N

Canonical SMILES

CCC(C)C(C(=O)NC(CC1=CNC=N1)C(=O)NC(CCC(=O)N)C(=O)NC(CCC(=O)N)C(=O)NC(CC(=O)O)C(=O)NC(CC2=CC=CC=C2)C(=O)NC(C(C)C)C(=O)NC(CC(=O)N)C(=O)NC(CC3=CNC4=CC=CC=C43)C(=O)NC(CC(C)C)C(=O)NC(CC(C)C)C(=O)NC(C)C(=O)NC(CCC(=O)N)C(=O)NC(CCCCN)C(=O)NCC(=O)NC(CCCCN)C(=O)NC(CCCCN)C(=O)NC(CC(=O)N)C(=O)NC(CC(=O)O)C(=O)NC(CC5=CNC6=CC=CC=C65)C(=O)NC(CCCCN)C(=O)NC(CC7=CNC=N7)C(=O)NC(CC(=O)N)C(=O)NC(C(C)CC)C(=O)NC(C(C)O)C(=O)NC(CCC(=O)N)C(=O)O)NC(=O)C(CCCCN)NC(=O)C(CC(=O)O)NC(=O)C(CCSC)NC(=O)C(C)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(CC8=CC=C(C=C8)O)NC(=O)C(CC(=O)O)NC(=O)C(CO)NC(=O)C(C(C)CC)NC(=O)C(CC9=CC=CC=C9)NC(=O)C(C(C)O)NC(=O)CNC(=O)C(CCC(=O)O)NC(=O)C(C)NC(=O)C(CC1=CC=C(C=C1)O)N

Isomeric SMILES

CC[C@H](C)[C@@H](C(=O)N[C@@H](CC1=CNC=N1)C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H](CC2=CC=CC=C2)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(=O)N)C(=O)N[C@@H](CC3=CNC4=CC=CC=C43)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(=O)N)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H](CC5=CNC6=CC=CC=C65)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC7=CNC=N7)C(=O)N[C@@H](CC(=O)N)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCC(=O)N)C(=O)O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](CCSC)NC(=O)[C@H](C)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@H](CO)NC(=O)[C@H](CC8=CC=C(C=C8)O)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](CO)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@H](CC9=CC=CC=C9)NC(=O)[C@H]([C@@H](C)O)NC(=O)CNC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](C)NC(=O)[C@H](CC1=CC=C(C=C1)O)N

Physical and chemical properties of CID 90488736

Molecular Formula

C226H338N60O66S

Molecular Weight

4983.53

Storage condition

-20°C

Solubility of CID 90488736

Solvent Solubility Behavior Effect of Temperature Effect of pH
Water Readily soluble Solubility slightly increases with rising temperature Most stable at neutral pH (6–8); degrades under acidic conditions
Physiological saline Soluble Minor increase in solubility with elevated temperature Minimal sensitivity to pH changes; suitable for injection
Dilute acid solution Soluble, but prone to hydrolysis High temperature accelerates hydrolysis Highly acidic conditions cause degradation; unstable after dissolution
Dilute alkaline solution Slightly soluble to soluble Solubility increases with rising temperature Strongly alkaline conditions may cause peptide chain degradation
Ethanol Slightly soluble Slight increase in solubility with rising temperature Minimal pH effect; poor solubility overall
DMSO Soluble Increased temperature enhances dissolution rate Minimal effect of pH changes on solubility

Key Milestone of CID 90488736

Year Event Description
1930 First Discovery It was named "Gastric Inhibitory Polypeptide" (GIP), as it was initially observed to inhibit gastric acid secretion and gastric motility. It was first described by Perley and Chance in dog experiments.
1960s–1970s Structural Identification Scientists isolated and determined the amino acid sequence of GIP, confirming it as a 42-amino-acid peptide hormone secreted by K cells in the small intestine.
1970s Re-evaluation of Function Research found that GIP significantly increases after oral glucose intake and stimulates insulin release from pancreatic β-cells, leading to its reclassification as one of the incretins, alongside GLP-1.
1980s–1990s Receptor and Mechanism Studies The GIP receptor (GIPR) was cloned, confirming it as a G-protein-coupled receptor primarily expressed in pancreatic β-cells and adipose tissue, elucidating its role in glucose homeostasis and lipid metabolism.
2000s Link to Type 2 Diabetes Studies found that type 2 diabetes patients exhibit resistance to GIP's insulinotropic effects, but GIP may still play a role in lipid metabolism and bone metabolism, prompting renewed evaluation of its therapeutic potential.
2010s Development of Dual/Triple Receptor Agonists With the success of GLP-1 receptor agonists (such as liraglutide and semaglutide), scientists began exploring dual GIP/GLP-1 receptor agonists (such as tirzepatide) for synergistic effects.
2022 Tirzepatide Approved The U.S. FDA approved tirzepatide (Tirzepatide, marketed as Mounjaro®), a dual GIP/GLP-1 receptor agonist developed by Eli Lilly, for the treatment of type 2 diabetes, showing significant superiority over single GLP-1 agonists, marking GIP's transformation from an "overlooked incretin" to a therapeutic target.
2023–2024 Expanded Indications and Deepened Mechanisms Tirzepatide was approved for obesity treatment (marketed as Zepbound®). Multiple studies further revealed GIP's potential roles in energy balance, adipose tissue metabolism, and neuroprotection, driving the development of next-generation multi-target incretin drugs.

Applications of CID 90488736

GIP has several potential applications in medical and therapeutic contexts:

  • Diabetes Management: Understanding GIP's role in insulin secretion can aid in developing therapies for type 2 diabetes.
  • Obesity Treatment: Given its influence on appetite and fat accumulation, GIP may be targeted for obesity management strategies.
  • Bone Health: Research into GIP's role in bone remodeling could lead to new treatments for osteoporosis and related conditions .

Interaction Studies of CID 90488736

Studies have shown that GIP interacts with various biological systems and receptors:

  • Insulin Secretion: GIP enhances insulin release in response to oral glucose intake more effectively than intravenous administration.
  • Glucagon Secretion: It also stimulates glucagon release from alpha cells in the pancreas, indicating a complex regulatory role in glucose metabolism.
  • Central Nervous System: GIP's receptors are present in the brain, suggesting involvement in cognitive functions related to memory and appetite regulation .

Biological Activity of CID 90488736

GIP's biological activity extends beyond insulin secretion. It has been shown to:

  • Inhibit apoptosis of pancreatic beta cells and promote their proliferation.
  • Stimulate glucagon secretion.
  • Influence appetite regulation and memory formation through actions in the central nervous system.
  • Play a role in bone remodeling, with studies indicating that GIP receptor deficiency can adversely affect bone quality .

Notably, individuals with type 2 diabetes often exhibit diminished responses to GIP, which correlates with lower levels of GIP secretion post-meal compared to non-diabetics .