c_di_AMP – Cyclic-di-adenylate

Name
WID c_di_AMP View in model
Name Cyclic-di-adenylate View in model
Traditional name 8,17-bis(6-aminopurin-9-yl)-9,18-dihydroxy-3,12- dioxo-2,4,7,11,13,16-hexaoxa-3$l^{5},12$l^{5}- diphosphatricyclo[13.3.0.0^{6,10}]octadecane-3,12- bis(olate)
IUPAC name 8,17-bis(6-amino-9H-purin-9-yl)-9,18-dihydroxy- 3,12-dioxo-2,4,7,11,13,16-hexaoxa-3$l^{5},12$l^{5}- diphosphatricyclo[13.3.0.0^{6,10}]octadecane-3,12- bis(olate)
 
Structure
Empirical formula (pH 7.5) H22C20N10O12P2
SMILES (pH 7.5) NC1=NC=NC2=C1N=CN2C1OC2COP([O-])(=O)[O-]C3C(COP([O-])(=O)[O-]C2C1O)OC(C3O)N1C=NC2=C1N=CN=C2N
Charge (pH 7.5) -2
Is hydrophobic False View in model
Molecular weight (Da) 656.40 View in model
van der Waals volume 
(pH 7.5; Å3 molecule‑1)
479.74
pI 3.95
logP -8.10
logD (pH 7.5) -7.39
 
Function
Reaction participant diadenylate cyclase
[c]: (2) ATPc_di_AMP + (2) PPI
View in model
 
Comments
Comments c-di-AMP may act as second messenger, similar to c-di-GMP to regulate Spo0A [PUB_0512]. c-di-AMP may secreted and trigger a host response [PUB_0683]. Media concentration set to value in Serrano et al M. pneumoniae minimal media [PUB_0614].
References
  1. Witte G, Hartung S, Büttner K, Hopfner KP. Structural biochemistry of a bacterial checkpoint protein reveals diadenylate cyclase activity regulated by DNA recombination intermediates. Mol Cell 30, 167-78 (2008). WholeCell: PUB_0512, PubMed: 18439896

  2. Woodward JJ, Iavarone AT, Portnoy DA. c-di-AMP secreted by intracellular Listeria monocytogenes activates a host type I interferon response. Science 328, 1703-5 (2010). WholeCell: PUB_0683, PubMed: 20508090

  3. Yus E, Maier T, Michalodimitrakis K, van Noort V, Yamada T, Chen WH, Wodke JA, Güell M, Martínez S, Bourgeois R, Kühner S, Raineri E, Letunic I, Kalinina OV, Rode M, Herrmann R, Gutiérrez-Gallego R, Russell RB, Gavin AC, Bork P, Serrano L. Impact of genome reduction on bacterial metabolism and its regulation. Science 326, 1263-8 (2009). WholeCell: PUB_0614, PubMed: 19965476

 
Metadata
Created 2012-10-01 15:06:51
Last updated 2012-10-01 15:11:56