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MedKoo Cat#: 412805 | Name: 2,3-CGAMP
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

2,3-CGAMP, or 2',3'-CGAMP, also known as Cgamp is the first cyclic di-nucleotide found in metazoa. In mammalian cells, cGAMP is synthesized by cyclic GMP-AMP synthase from ATP and GTP upon cytosolic DNA stimulation.

Chemical Structure

2,3-CGAMP
2,3-CGAMP
CAS#1441190-66-4

Theoretical Analysis

MedKoo Cat#: 412805

Name: 2,3-CGAMP

CAS#: 1441190-66-4

Chemical Formula: C20H24N10O13P2

Exact Mass: 674.1000

Molecular Weight: 674.42

Elemental Analysis: C, 35.62; H, 3.59; N, 20.77; O, 30.84; P, 9.19

Price and Availability

Size Price Availability Quantity
1mg USD 550.00 2 Weeks
5mg USD 1,250.00 2 Weeks
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Related CAS #
No Data
Synonym
2,3-CGAMP; Cgamp; C-20640; C 20640; C20640; 2′-3′-cyclic GMP-AMP; cGAMP(2′→5′); Cyclic Gp(2′→5′)Ap(3′→5′);
IUPAC/Chemical Name
2-Amino-9-((1R,6R,8R,9R,10S,15R,17R,18R)-8-(6-amino-9H-purin-9-yl)-3,9,12,18-tetrahydroxy-3,12-dioxido-2,4,7,11,13,16-hexaoxa-3,12-diphosphatricyclo(13.2.1.06,10)octadec-17-yl)-1,9-dihydro-6H-purin-6-one
InChi Key
XRILCFTWUCUKJR-INFSMZHSSA-N
InChi Code
InChI=1S/C20H24N10O13P2/c21-14-8-15(24-3-23-14)29(4-25-8)18-11(32)12-7(41-18)2-39-45(36,37)43-13-10(31)6(1-38-44(34,35)42-12)40-19(13)30-5-26-9-16(30)27-20(22)28-17(9)33/h3-7,10-13,18-19,31-32H,1-2H2,(H,34,35)(H,36,37)(H2,21,23,24)(H3,22,27,28,33)/t6-,7-,10-,11-,12-,13-,18-,19-/m1/s1
SMILES Code
O[C@H]1[C@@]2([C@@](O[C@@]1(COP(=O)(O)O[C@@]3([C@@](COP(=O)(O)O2)(O[C@]([C@@H]3O)(N4C=5C(N=C4)=C(N)N=CN5)[H])[H])[H])[H])(N6C7=C(N=C6)C(=O)N=C(N)N7)[H])[H]
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 674.42 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Swanson KV, Junkins RD, Kurkjian CJ, Holley-Guthrie E, Pendse AA, El Morabiti R, Petrucelli A, Barber GN, Benedict CA, Ting JP. A noncanonical function of cGAMP in inflammasome priming and activation. J Exp Med. 2017 Dec 4;214(12):3611-3626. doi: 10.1084/jem.20171749. Epub 2017 Oct 13. PMID: 29030458; PMCID: PMC5716045. 2: Li T, Chen ZJ. The cGAS-cGAMP-STING pathway connects DNA damage to inflammation, senescence, and cancer. J Exp Med. 2018 May 7;215(5):1287-1299. doi: 10.1084/jem.20180139. Epub 2018 Apr 5. PMID: 29622565; PMCID: PMC5940270. 3: Ritchie C, Cordova AF, Hess GT, Bassik MC, Li L. SLC19A1 Is an Importer of the Immunotransmitter cGAMP. Mol Cell. 2019 Jul 25;75(2):372-381.e5. doi: 10.1016/j.molcel.2019.05.006. Epub 2019 May 21. PMID: 31126740; PMCID: PMC6711396. 4: Schwede F, Genieser HG, Rentsch A. The Chemistry of the Noncanonical Cyclic Dinucleotide 2'3'-cGAMP and Its Analogs. Handb Exp Pharmacol. 2017;238:359-384. doi: 10.1007/164_2015_43. PMID: 27392950. 5: Gentili M, Kowal J, Tkach M, Satoh T, Lahaye X, Conrad C, Boyron M, Lombard B, Durand S, Kroemer G, Loew D, Dalod M, Théry C, Manel N. Transmission of innate immune signaling by packaging of cGAMP in viral particles. Science. 2015 Sep 11;349(6253):1232-6. doi: 10.1126/science.aab3628. Epub 2015 Jul 30. PMID: 26229115. 6: Li T, Cheng H, Yuan H, Xu Q, Shu C, Zhang Y, Xu P, Tan J, Rui Y, Li P, Tan X. Antitumor Activity of cGAMP via Stimulation of cGAS-cGAMP-STING-IRF3 Mediated Innate Immune Response. Sci Rep. 2016 Jan 12;6:19049. doi: 10.1038/srep19049. PMID: 26754564; PMCID: PMC4709567. 7: Bai J, Liu F. The cGAS-cGAMP-STING Pathway: A Molecular Link Between Immunity and Metabolism. Diabetes. 2019 Jun;68(6):1099-1108. doi: 10.2337/dbi18-0052. PMID: 31109939; PMCID: PMC6610018. 8: Bai J, Cervantes C, Liu J, He S, Zhou H, Zhang B, Cai H, Yin D, Hu D, Li Z, Chen H, Gao X, Wang F, O'Connor JC, Xu Y, Liu M, Dong LQ, Liu F. DsbA-L prevents obesity-induced inflammation and insulin resistance by suppressing the mtDNA release-activated cGAS-cGAMP-STING pathway. Proc Natl Acad Sci U S A. 2017 Nov 14;114(46):12196-12201. doi: 10.1073/pnas.1708744114. Epub 2017 Oct 30. PMID: 29087318; PMCID: PMC5699051. 9: Eaglesham JB, Pan Y, Kupper TS, Kranzusch PJ. Viral and metazoan poxins are cGAMP-specific nucleases that restrict cGAS-STING signalling. Nature. 2019 Feb;566(7743):259-263. doi: 10.1038/s41586-019-0928-6. Epub 2019 Feb 6. Erratum in: Nature. 2019 May 13;: PMID: 30728498; PMCID: PMC6640140. 10: Chen Q, Boire A, Jin X, Valiente M, Er EE, Lopez-Soto A, Jacob L, Patwa R, Shah H, Xu K, Cross JR, Massagué J. Carcinoma-astrocyte gap junctions promote brain metastasis by cGAMP transfer. Nature. 2016 May 26;533(7604):493-498. doi: 10.1038/nature18268. Epub 2016 May 18. Erratum in: Nature. 2017 Apr 6;544(7648):124. PMID: 27225120; PMCID: PMC5021195.