2.0 2012-05-31 14:51:38 -0600 2015-06-03 17:20:20 -0600 ECMDB20579 M2MDB001381 Linear dimeric GMP Linear dimeric GMP is a member of the chemical class known as Purine Ribonucleoside 3',5'-Bisphosphates. These are purine ribobucleotides with one phosphate group attached to 3' and 5' hydroxyl groups of the ribose moiety. 5'-Monophosphate-guanylyl-3',5'-guanosine 5'-Monophosphoric acid-guanylyl-3',5'-guanosine 5'-Phosphoguanylyl(3'->5')guanosine 5'PGpG L-Di-GMP Nchembio.136-comp9 C20H23N10O15P2 705.4021 705.08195814 9-[(2R,3R,4S,5R)-4-[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(2-imino-6-oxido-3,9-dihydro-2H-purin-9-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]-5-[(hydrogen phosphonatooxy)methyl]-3-hydroxyoxolan-2-yl]-2-imino-3,9-dihydro-2H-purin-6-olate 9-[(2R,3R,4S,5R)-4-({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(2-imino-6-oxido-3H-purin-9-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy)-5-[(hydrogen phosphonatooxy)methyl]-3-hydroxyoxolan-2-yl]-2-imino-3H-purin-6-olate [H][C@]1(COP(O)(=O)O[C@]2([H])[C@@]([H])(COP(O)([O-])=O)O[C@@]([H])(N3C=NC4=C3NC(=N)N=C4[O-])[C@]2([H])O)O[C@@]([H])(N2C=NC3=C2NC(=N)N=C3[O-])[C@]([H])(O)[C@]1([H])O InChI=1S/C20H26N10O15P2/c21-19-25-13-7(15(34)27-19)23-3-29(13)17-10(32)9(31)5(43-17)1-42-47(39,40)45-12-6(2-41-46(36,37)38)44-18(11(12)33)30-4-24-8-14(30)26-20(22)28-16(8)35/h3-6,9-12,17-18,31-33H,1-2H2,(H,39,40)(H2,36,37,38)(H3,21,25,27,34)(H3,22,26,28,35)/p-3/t5-,6-,9-,10-,11-,12-,17-,18-/m1/s1 ZEHOHLFQOXAZHX-MHARETSRSA-K Cytoplasm Periplasm logp -0.97 ALOGPS logs -2.22 ALOGPS solubility 4.56e+00 g/l ALOGPS logp -4.4 ChemAxon pka_strongest_acidic 1.13 ChemAxon pka_strongest_basic 5.16 ChemAxon iupac 9-[(2R,3R,4S,5R)-4-[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(2-imino-6-oxido-3,9-dihydro-2H-purin-9-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]-5-[(hydrogen phosphonatooxy)methyl]-3-hydroxyoxolan-2-yl]-2-imino-3,9-dihydro-2H-purin-6-olate ChemAxon average_mass 705.4021 ChemAxon mono_mass 705.08195814 ChemAxon smiles [H][C@]1(COP(O)(=O)O[C@]2([H])[C@@]([H])(COP(O)([O-])=O)O[C@@]([H])(N3C=NC4=C3NC(=N)N=C4[O-])[C@]2([H])O)O[C@@]([H])(N2C=NC3=C2NC(=N)N=C3[O-])[C@]([H])(O)[C@]1([H])O ChemAxon formula C20H23N10O15P2 ChemAxon inchi InChI=1S/C20H26N10O15P2/c21-19-25-13-7(15(34)27-19)23-3-29(13)17-10(32)9(31)5(43-17)1-42-47(39,40)45-12-6(2-41-46(36,37)38)44-18(11(12)33)30-4-24-8-14(30)26-20(22)28-16(8)35/h3-6,9-12,17-18,31-33H,1-2H2,(H,39,40)(H2,36,37,38)(H3,21,25,27,34)(H3,22,26,28,35)/p-3/t5-,6-,9-,10-,11-,12-,17-,18-/m1/s1 ChemAxon inchikey ZEHOHLFQOXAZHX-MHARETSRSA-K ChemAxon polar_surface_area 382.74 ChemAxon refractivity 188.35 ChemAxon polarizability 59.93 ChemAxon rotatable_bond_count 10 ChemAxon acceptor_count 20 ChemAxon donor_count 9 ChemAxon physiological_charge -3 ChemAxon formal_charge -3 ChemAxon Specdb::NmrOneD 283649 Specdb::NmrOneD 283650 Specdb::NmrOneD 283651 Specdb::NmrOneD 283652 Specdb::NmrOneD 283653 Specdb::NmrOneD 283654 Specdb::NmrOneD 283655 Specdb::NmrOneD 283656 Specdb::NmrOneD 283657 Specdb::NmrOneD 283658 Specdb::NmrOneD 283659 Specdb::NmrOneD 283660 Specdb::NmrOneD 283661 Specdb::NmrOneD 283662 Specdb::NmrOneD 283663 Specdb::NmrOneD 283664 Specdb::NmrOneD 283665 Specdb::NmrOneD 283666 Specdb::NmrOneD 283667 Specdb::NmrOneD 283668 Specdb::MsMs 27581 Specdb::MsMs 27582 Specdb::MsMs 27583 Specdb::MsMs 34139 Specdb::MsMs 34140 Specdb::MsMs 34141 25093482 24605057 C18076 L-DI-GMP Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. 21097882 Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. 22080510 Cyclic di-GMP phosphodiesterase yahA P21514 YAHA_ECOLI yahA http://ecmdb.ca/proteins/P21514.xml Oxygen sensor protein DosP P76129 DOSP_ECOLI dosP http://ecmdb.ca/proteins/P76129.xml 3',5'-Cyclic diGMP + Water + Cyclic di-3',5'-guanylate <> Linear dimeric GMP R08991 cyclic di-3',5'-guanylate + Water > Hydrogen ion + Linear dimeric GMP RXN0-4181