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C-di-amp

CAS No.:
54447-84-6
Catalog Number:
AG00D9YA
Molecular Formula:
C20H24N10O12P2
Molecular Weight:
658.4119
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
1mg
99%
1 week
United States
$307
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Product Description
Catalog Number:
AG00D9YA
Chemical Name:
C-di-amp
CAS Number:
54447-84-6
Molecular Formula:
C20H24N10O12P2
Molecular Weight:
658.4119
IUPAC Name:
(1S,6R,8R,9R,10S,15R,17R,18R)-8,17-bis(6-aminopurin-9-yl)-3,12-dihydroxy-3,12-dioxo-2,4,7,11,13,16-hexaoxa-3λ5,12λ5-diphosphatricyclo[13.3.0.06,10]octadecane-9,18-diol
InChI:
InChI=1S/C20H24N10O12P2/c21-15-9-17(25-3-23-15)29(5-27-9)19-11(31)13-7(39-19)1-37-43(33,34)42-14-8(2-38-44(35,36)41-13)40-20(12(14)32)30-6-28-10-16(22)24-4-26-18(10)30/h3-8,11-14,19-20,31-32H,1-2H2,(H,33,34)(H,35,36)(H2,21,23,25)(H2,22,24,26)/t7-,8-,11-,12-,13-,14-,19-,20-/m1/s1
InChI Key:
PDXMFTWFFKBFIN-XPWFQUROSA-N
SMILES:
O[C@@H]1[C@@H]2OP(=O)(O)OC[C@H]3O[C@H]([C@@H]([C@@H]3OP(=O)(OC[C@H]2O[C@H]1n1cnc2c1ncnc2N)O)O)n1cnc2c1ncnc2N
Properties
Complexity:
1080  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
8  
Defined Bond Stereocenter Count:
0
Exact Mass:
658.105g/mol
Formal Charge:
0
Heavy Atom Count:
44  
Hydrogen Bond Acceptor Count:
20  
Hydrogen Bond Donor Count:
6  
Isotope Atom Count:
0
Molecular Weight:
658.418g/mol
Monoisotopic Mass:
658.105g/mol
Rotatable Bond Count:
2  
Topological Polar Surface Area:
310A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-5.1  
Literature
Title Journal
Mycobacterium tuberculosis Rv3586 (DacA) is a diadenylate cyclase that converts ATP or ADP into c-di-AMP. PloS one 20120101
c-di-AMP is a new second messenger in Staphylococcus aureus with a role in controlling cell size and envelope stress. PLoS pathogens 20110901
Bis-(3',5')-cyclic dimeric adenosine monophosphate: strong Th1/Th2/Th17 promoting mucosal adjuvant. Vaccine 20110718
c-di-AMP reports DNA integrity during sporulation in Bacillus subtilis. EMBO reports 20110601
Identification of a Streptococcus pyogenes SF370 gene involved in production of c-di-AMP. Nagoya journal of medical science 20110201
c-di-AMP secreted by intracellular Listeria monocytogenes activates a host type I interferon response. Science (New York, N.Y.) 20100625
YybT is a signaling protein that contains a cyclic dinucleotide phosphodiesterase domain and a GGDEF domain with ATPase activity. The Journal of biological chemistry 20100101
Structural basis of ligand binding by a c-di-GMP riboswitch. Nature structural & molecular biology 20091201
Great times for small molecules: c-di-AMP, a second messenger candidate in Bacteria and Archaea. Science signaling 20080819
Structural biochemistry of a bacterial checkpoint protein reveals diadenylate cyclase activity regulated by DNA recombination intermediates. Molecular cell 20080425
Properties