CAS 61093-23-0

c-Di-GMP

Description:

c-Di-GMP, or cyclic diguanylate, is a second messenger molecule predominantly found in bacteria, playing a crucial role in regulating various cellular processes. It is characterized by its cyclic structure, which consists of two guanosine monophosphate (GMP) units linked by phosphodiester bonds. This molecule is involved in the regulation of biofilm formation, motility, and virulence in bacterial cells. c-Di-GMP acts by binding to specific receptor proteins, influencing downstream signaling pathways that affect gene expression and cellular behavior. Its levels are tightly regulated by diguanylate cyclases, which synthesize c-Di-GMP, and phosphodiesterases, which degrade it. The balance of c-Di-GMP is essential for bacterial adaptation to environmental changes, making it a significant target for research in microbiology and potential therapeutic applications. Additionally, c-Di-GMP has been studied for its role in the transition between planktonic and sessile lifestyles in bacteria, highlighting its importance in microbial ecology and pathogenesis.

Formula: C₂₀H₂₄N₁₀O₁₄P₂

InChI: InChI=1S/C20H24N10O14P2/c21-19-25-13-7(15(33)27-19)23-3-29(13)17-9(31)11-5(41-17)1-39-45(35,36)44-12-6(2-40-46(37,38)43-11)42-18(10(12)32)30-4-24-8-14(30)26-20(22)28-16(8)34/h3-6,9-12,17-18,31-32H,1-2H2,(H,35,36)(H,37,38)(H3,21,25,27,33)(H3,22,26,28,34)/t5-,6-,9-,10-,11-,12-,17-,18-/m1/s1

InChI key: InChIKey=PKFDLKSEZWEFGL-MHARETSRSA-N

SMILES: O=C1C2=C(N(C=N2)[C@H]3[C@H](O)[C@]4([C@](O3)(COP(=O)(O)O[C@@]5([C@@](COP(=O)(O)O4)(O[C@H]([C@@H]5O)N6C7=C(N=C6)C(=O)N=C(N)N7)[H])[H])[H])[H])NC(N)=N1

Synonyms:

• 3′-Guanylic acid, guanylyl-(3′→5′)-, cyclic nucleotide
• Cyclic-di-GMP
• 2H,7H-Difuro[3,2-d:3′,2′-j][1,3,7,9,2,8]tetraoxadiphosphacyclododecin, 3′-guanylic acid deriv.
• c-Di-GMP
• Cyclic diguanylate
• 5GP-5GP
• Cyclic diguanosine monophosphate ( c-diGMP/c-di-GMP ) / cyclic bis ( 3' > 5' ) diguanylic acid
• bis(3',5')-cyclic diguanylic acid
• Cyclic-di-GMP，cyclic diguanylate
• Cyclic-di-GMP(c-di-GMP)

bis(3',5')-cyclic diguanylic acid

CAS: 61093-23-0

Complexity 1340
Compound Is Canonicalized Yes
Covalently-Bonded Unit Count 1
Defined Atom Stereocenter Count 8
Defined Bond Stereocenter Count 0
Exact Mass 690.095g/mol
Formal Charge 0
Heavy Atom Count 46
Hydrogen Bond Acceptor Count 18
Hydrogen Bond Donor Count 8
Isotope Atom Count 0
Molecular Weight 690.416g/mol
Monoisotopic Mass 690.095g/mol
Rotatable Bond Count 2
Topological Polar Surface Area 341A^2
Undefined Atom Stereocenter Count 0
Undefined Bond Stereocenter Count 0
XLogP3 -6.8

Formula: C₂₀H₂₄N₁₀O₁₄P₂

Purity: 97%

Color and Shape: Solid

Molecular weight: 690.4107

Ref: IN-DA00EPOT

Cyclic-di-GMP

Controlled Product

CAS: 61093-23-0

Formula: C₂₀H₂₄N₁₀O₁₄P₂

Color and Shape: Neat

Molecular weight: 690.411

Ref: TR-C987353

Cyclic-di-GMP-13C2,15N4

Controlled Product

CAS: 61093-23-0

Formula: C₂C₁₈H₂₄₁₅N₄N₆O₁₄P₂

Color and Shape: Neat

Molecular weight: 696.37

Ref: TR-C987354

Cyclic diguanosine monophosphate

CAS: 61093-23-0

Cyclic diguanosine monophosphate (c-di-GMP) is a nucleotide that is involved in bacterial cell signaling. It has been shown to be essential for the formation of bacterial biofilms and plays an important role in the development of infectious diseases. c-di-GMP is synthesized from guanosine triphosphate through a series of enzymatic reactions and then hydrolyzed by cyclic diguanosine monophosphatase, which leads to its termination as a second messenger. c-di-GMP interacts with proteins that regulate the expression of genes involved in biofilm formation, motility, and virulence. The synthesis and hydrolysis of c-di-GMP are regulated by multiple enzymes, including protein phosphatases, that control cellular physiology such as biofilm formation.

Formula: C₂₀H₂₄N₁₀O₁₄P₂

Purity: Min. 95%

Molecular weight: 690.41 g/mol

Ref: 3D-NC46014

Cyclic-di-GMP

CAS: 61093-23-0

Cyclic-di-GMP is a STING agonist and ubiquitous second messenger, which regulates the formation, motility and virulence of biofilms in various bacterial species

Formula: C₂₀H₂₄N₁₀O₁₄P₂

Purity: 98%

Color and Shape: Solid

Molecular weight: 690.41

Ref: TM-T10909