1.0 2016-09-30 22:44:00 UTC 2020-05-21 15:38:42 UTC BMDB0001314 BMDB01314 Cyclic GMP Cyclic GMP, also known as CGMP or GMP, cyclic, belongs to the class of organic compounds known as 3',5'-cyclic purine nucleotides. These are purine nucleotides in which the oxygen atoms linked to the C3 and C5 carbon atoms of the ribose moiety are both bonded the same phosphorus atom of the phosphate group. Cyclic GMP is possibly soluble (in water) and a moderately basic compound (based on its pKa). Cyclic GMP exists in all living species, ranging from bacteria to humans. In cattle, cyclic GMP is involved in the metabolic pathway called ion channels and their functional role in vascular endothelium pathway. CGMP Guanosine 3',5'-cyclic monophosphate Guanosine 3',5'-cyclic phosphate Guanosine cyclic monophosphate Guanosine 3',5'-cyclic monophosphoric acid Guanosine 3',5'-cyclic phosphoric acid Guanosine cyclic monophosphoric acid 3',5'-Cyclic GMP 3',5'-Guanosine 3',5'-Guanosine monophosphate Cyclic 3',5'-guanosine monophosphate Cyclic guanosine 3',5'-monophosphate Cyclic-GMP Guanosine 3',5'-cyclic-monophosphate Guanosine 3',5'-monophosphate Guanosine cyclic-monophosphate Guanosine-cyclic-phosphoric-acid Cyclic 3',5'-monophosphate, guanosine GMP, Cyclic Guanosine cyclic-3',5'-monophosphate monoPhosphate, guanosine cyclic 3',5'-monoPhosphate, guanosine cyclic Cyclic-3',5'-monophosphate, guanosine Guanosine cyclic 3',5'-monophosphate Guanosine cyclic 3,5 monophosphate Cyclic monophosphate, guanosine Guanosine cyclic 3',5' monophosphate C10H12N5O7P 345.2053 345.047434275 9-[(4aR,6R,7R,7aS)-2,7-dihydroxy-2-oxo-hexahydro-2λ⁵-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl]-2-amino-6,9-dihydro-1H-purin-6-one cyclic-GMP 7665-99-8 NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(O)(=O)O[C@H]3[C@H]2O)C(=O)N1 InChI=1S/C10H12N5O7P/c11-10-13-7-4(8(17)14-10)12-2-15(7)9-5(16)6-3(21-9)1-20-23(18,19)22-6/h2-3,5-6,9,16H,1H2,(H,18,19)(H3,11,13,14,17)/t3-,5-,6-,9-/m1/s1 ZOOGRGPOEVQQDX-UUOKFMHZSA-N belongs to the class of organic compounds known as 3',5'-cyclic purine nucleotides. These are purine nucleotides in which the oxygen atoms linked to the C3 and C5 carbon atoms of the ribose moiety are both bonded the same phosphorus atom of the phosphate group. Organic compounds Nucleosides, nucleotides, and analogues Purine nucleotides Cyclic purine nucleotides 3',5'-cyclic purine nucleotides 6-oxopurines Aminopyrimidines and derivatives Azacyclic compounds Glycosylamines Heteroaromatic compounds Hydrocarbon derivatives Hypoxanthines Monosaccharide phosphates N-substituted imidazoles Organic oxides Organic phosphoric acids and derivatives Organopnictogen compounds Oxacyclic compounds Pentose phosphates Primary amines Pyrimidones Secondary alcohols Tetrahydrofurans Vinylogous amides 3',5'-cyclic purine ribonucleotide 6-oxopurine Alcohol Amine Aminopyrimidine Aromatic heteropolycyclic compound Azacycle Azole Glycosyl compound Heteroaromatic compound Hydrocarbon derivative Hypoxanthine Imidazole Imidazopyrimidine Monosaccharide Monosaccharide phosphate N-glycosyl compound N-substituted imidazole Organic nitrogen compound Organic oxide Organic oxygen compound Organic phosphoric acid derivative Organoheterocyclic compound Organonitrogen compound Organooxygen compound Organopnictogen compound Oxacycle Pentose phosphate Primary amine Purine Purinone Pyrimidine Pyrimidone Secondary alcohol Tetrahydrofuran Vinylogous amide Aromatic heteropolycyclic compounds 3',5'-Cyclic nuclcleotides 3',5'-cyclic purine nucleotide guanyl ribonucleotide Solid logp -1.98 ALOGPS logs -1.96 ALOGPS logp -2.1 ChemAxon pka_strongest_acidic 2.05 ChemAxon pka_strongest_basic 1.41 ChemAxon iupac 9-[(4aR,6R,7R,7aS)-2,7-dihydroxy-2-oxo-hexahydro-2λ⁵-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl]-2-amino-6,9-dihydro-1H-purin-6-one ChemAxon average_mass 345.2053 ChemAxon mono_mass 345.047434275 ChemAxon smiles NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(O)(=O)O[C@H]3[C@H]2O)C(=O)N1 ChemAxon formula C10H12N5O7P ChemAxon inchi InChI=1S/C10H12N5O7P/c11-10-13-7-4(8(17)14-10)12-2-15(7)9-5(16)6-3(21-9)1-20-23(18,19)22-6/h2-3,5-6,9,16H,1H2,(H,18,19)(H3,11,13,14,17)/t3-,5-,6-,9-/m1/s1 ChemAxon inchikey ZOOGRGPOEVQQDX-UUOKFMHZSA-N ChemAxon polar_surface_area 170.52 ChemAxon refractivity 71.72 ChemAxon polarizability 29.19 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 8 ChemAxon donor_count 4 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 4 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Ion Channels and Their Functional Role in Vascular Endothelium SMP0108207 Specdb::CMs 2262 Specdb::CMs 23461 Specdb::CMs 31308 Specdb::CMs 38019 Specdb::CMs 137880 Specdb::CMs 145614 Specdb::NmrOneD 248448 Specdb::NmrOneD 248449 Specdb::NmrOneD 248450 Specdb::NmrOneD 248451 Specdb::NmrOneD 248452 Specdb::NmrOneD 248453 Specdb::NmrOneD 248454 Specdb::NmrOneD 248455 Specdb::NmrOneD 248456 Specdb::NmrOneD 248457 Specdb::NmrOneD 248458 Specdb::NmrOneD 248459 Specdb::NmrOneD 248460 Specdb::NmrOneD 248461 Specdb::NmrOneD 248462 Specdb::NmrOneD 248463 Specdb::NmrOneD 248464 Specdb::NmrOneD 248465 Specdb::NmrOneD 248466 Specdb::NmrOneD 248467 Specdb::MsMs 25964 Specdb::MsMs 25965 Specdb::MsMs 25966 Specdb::MsMs 32522 Specdb::MsMs 32523 Specdb::MsMs 32524 Specdb::MsMs 439074 Specdb::MsMs 439590 Specdb::MsMs 439591 Specdb::MsMs 439592 Specdb::MsMs 439593 Specdb::MsMs 439594 Specdb::MsMs 440098 Specdb::MsMs 448015 Specdb::MsMs 449660 Specdb::MsMs 449661 Specdb::MsMs 449662 Specdb::MsMs 449663 Specdb::MsMs 449664 Specdb::MsMs 449665 Specdb::MsMs 449666 Specdb::MsMs 449667 Specdb::MsMs 449668 Specdb::MsMs 449669 Specdb::MsMs 449670 Kidney Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Liver 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under corn stover based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Liver 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under alfalfa hay based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Mammary Gland 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under corn stover based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Mammary Gland 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under alfalfa hay based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Platelet Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Smooth Muscle Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 C00942 22734 24316 DB02315 FDB030764 16356 C00019673 1485267 Cyclic guanosine monophosphate 6152 Sekhar, Konjeti R.; Grondin, Pascal; Francis, Sharron H.; Corbin, Jackie D. Design and synthesis of xanthines and cyclic GMP analogs as potent inhibitors of PDE5. Phosphodiesterase Inhibitors (1996), 135-146. BMDBP00029 Guanylate cyclase soluble subunit beta-1 P16068 GUCY1B1 Enzyme BMDBP00429 Cone cGMP-specific 3',5'-cyclic phosphodiesterase subunit alpha' P16586 PDE6C Enzyme BMDBP00430 Rod cGMP-specific 3',5'-cyclic phosphodiesterase subunit alpha P11541 PDE6A Enzyme BMDBP00431 Rod cGMP-specific 3',5'-cyclic phosphodiesterase subunit beta P23439 PDE6B Enzyme BMDBP00433 Retinal cone rhodopsin-sensitive cGMP 3',5'-cyclic phosphodiesterase subunit gamma P22571 PDE6H Enzyme BMDBP00434 cGMP-specific 3',5'-cyclic phosphodiesterase Q28156 PDE5A Enzyme BMDBP00435 Retinal rod rhodopsin-sensitive cGMP 3',5'-cyclic phosphodiesterase subunit gamma P04972 PDE6G Enzyme BMDBP00436 Atrial natriuretic peptide receptor 2 P46197 NPR2 Enzyme BMDBP01109 Retinal guanylyl cyclase 2 O02740 GUCY2F Enzyme BMDBP01117 Guanylate cyclase soluble subunit alpha-1 P19687 GUCY1A1 Enzyme BMDBP01122 Guanylate cyclase O77690 Enzyme BMDBP01125 Retinal guanylyl cyclase 1 P55203 GUCY2D Enzyme BMDBP01179 cGMP-dependent protein kinase 1 P00516 PRKG1 Enzyme BMDBP01256 cGMP-dependent 3',5'-cyclic phosphodiesterase P14099 PDE2A Enzyme BMDBP01337 Inositol 1,4,5-trisphosphate receptor type 1 Q9TU34 ITPR1 Enzyme BMDBP02679 cGMP-gated cation channel alpha-1 Q00194 CNGA1 Enzyme BMDBP02680 Cyclic nucleotide-gated cation channel alpha-3 Q29441 CNGA3 Enzyme