Hmdb loader
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-09-22 17:43:46 UTC
HMDB IDHMDB0001314
Secondary Accession Numbers
  • HMDB01314
Metabolite Identification
Common NameCyclic GMP
DescriptionCyclic GMP, also known as CGMP or 3',5'-cyclic GMP, 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 a moderately basic compound (based on its pKa). Cyclic GMP exists in all living species, ranging from bacteria to humans. In humans, cyclic GMP is involved in ion channels and their functional role in vascular endothelium. Outside of the human body, Cyclic GMP has been detected, but not quantified in, several different foods, such as rose hips, garden rhubarbs, acerola, nectarines, and passion fruits. This could make cyclic GMP a potential biomarker for the consumption of these foods. A 3',5'-cyclic purine nucleotide in which the purine nucleobase is specified as guanidine.
Structure
Data?1582752191
Synonyms
ValueSource
CGMPChEBI
Guanosine 3',5'-cyclic monophosphateChEBI
Guanosine 3',5'-cyclic phosphateChEBI
Guanosine cyclic monophosphateChEBI
Guanosine 3',5'-cyclic monophosphoric acidGenerator
Guanosine 3',5'-cyclic phosphoric acidGenerator
Guanosine cyclic monophosphoric acidGenerator
3',5'-Cyclic GMPHMDB
3',5'-GuanosineHMDB
3',5'-Guanosine monophosphateHMDB
Cyclic 3',5'-guanosine monophosphateHMDB
Cyclic guanosine 3',5'-monophosphateHMDB
Cyclic-GMPHMDB
Guanosine 3',5'-cyclic-monophosphateHMDB
Guanosine 3',5'-monophosphateHMDB
Guanosine cyclic-monophosphateHMDB
Guanosine-cyclic-phosphoric-acidHMDB
Cyclic 3',5'-monophosphate, guanosineHMDB
GMP, CyclicHMDB
Guanosine cyclic-3',5'-monophosphateHMDB
monoPhosphate, guanosine cyclicHMDB
3',5'-monoPhosphate, guanosine cyclicHMDB
Cyclic-3',5'-monophosphate, guanosineHMDB
Guanosine cyclic 3',5'-monophosphateHMDB
Guanosine cyclic 3,5 monophosphateHMDB
Cyclic monophosphate, guanosineHMDB
Guanosine cyclic 3',5' monophosphateHMDB
Chemical FormulaC10H12N5O7P
Average Molecular Weight345.2053
Monoisotopic Molecular Weight345.047434275
IUPAC Name9-[(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
Traditional Namecyclic-GMP
CAS Registry Number7665-99-8
SMILES
NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(O)(=O)O[C@H]3[C@H]2O)C(=O)N1
InChI Identifier
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
InChI KeyZOOGRGPOEVQQDX-UUOKFMHZSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleotides
Sub ClassCyclic purine nucleotides
Direct Parent3',5'-cyclic purine nucleotides
Alternative Parents
Substituents
  • 3',5'-cyclic purine ribonucleotide
  • Pentose phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • 6-oxopurine
  • Hypoxanthine
  • Monosaccharide phosphate
  • Purinone
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Pyrimidone
  • Monosaccharide
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Pyrimidine
  • Vinylogous amide
  • Azole
  • Tetrahydrofuran
  • Heteroaromatic compound
  • Imidazole
  • Secondary alcohol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Alcohol
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxide
  • Primary amine
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Not Available167.0http://allccs.zhulab.cn/database/detail?ID=AllCCS00000166
[M+H]+Not Available172.6http://allccs.zhulab.cn/database/detail?ID=AllCCS00000166
Predicted Molecular Properties
PropertyValueSource
Water Solubility3.79 g/LALOGPS
logP-2ALOGPS
logP-2.1ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)2.05ChemAxon
pKa (Strongest Basic)1.41ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area170.52 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity71.72 m³·mol⁻¹ChemAxon
Polarizability29.19 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+176.99231661259
DarkChem[M-H]-169.70531661259
AllCCS[M+H]+174.11132859911
AllCCS[M-H]-168.8232859911
DeepCCS[M+H]+174.87530932474
DeepCCS[M-H]-172.37530932474
DeepCCS[M-2H]-207.20230932474
DeepCCS[M+Na]+182.99230932474
AllCCS[M+H]+174.132859911
AllCCS[M+H-H2O]+171.132859911
AllCCS[M+NH4]+176.932859911
AllCCS[M+Na]+177.732859911
AllCCS[M-H]-168.832859911
AllCCS[M+Na-2H]-168.232859911
AllCCS[M+HCOO]-167.632859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Cyclic GMP,1TMS,isomer #1C[Si](C)(C)O[C@@H]1[C@@H]2OP(=O)(O)OC[C@H]2O[C@H]1N1C=NC2=C1N=C(N)[NH]C2=O3086.0Semi standard non polar33892256
Cyclic GMP,1TMS,isomer #1C[Si](C)(C)O[C@@H]1[C@@H]2OP(=O)(O)OC[C@H]2O[C@H]1N1C=NC2=C1N=C(N)[NH]C2=O3034.9Standard non polar33892256
Cyclic GMP,1TMS,isomer #1C[Si](C)(C)O[C@@H]1[C@@H]2OP(=O)(O)OC[C@H]2O[C@H]1N1C=NC2=C1N=C(N)[NH]C2=O5327.3Standard polar33892256
Cyclic GMP,1TMS,isomer #2C[Si](C)(C)OP1(=O)OC[C@H]2O[C@@H](N3C=NC4=C3N=C(N)[NH]C4=O)[C@H](O)[C@@H]2O13063.5Semi standard non polar33892256
Cyclic GMP,1TMS,isomer #2C[Si](C)(C)OP1(=O)OC[C@H]2O[C@@H](N3C=NC4=C3N=C(N)[NH]C4=O)[C@H](O)[C@@H]2O13027.1Standard non polar33892256
Cyclic GMP,1TMS,isomer #2C[Si](C)(C)OP1(=O)OC[C@H]2O[C@@H](N3C=NC4=C3N=C(N)[NH]C4=O)[C@H](O)[C@@H]2O15034.6Standard polar33892256
Cyclic GMP,1TMS,isomer #3C[Si](C)(C)NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(=O)(O)O[C@H]3[C@H]2O)C(=O)[NH]13096.2Semi standard non polar33892256
Cyclic GMP,1TMS,isomer #3C[Si](C)(C)NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(=O)(O)O[C@H]3[C@H]2O)C(=O)[NH]13024.6Standard non polar33892256
Cyclic GMP,1TMS,isomer #3C[Si](C)(C)NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(=O)(O)O[C@H]3[C@H]2O)C(=O)[NH]15395.6Standard polar33892256
Cyclic GMP,1TMS,isomer #4C[Si](C)(C)N1C(N)=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(=O)(O)O[C@H]3[C@H]2O)C1=O3123.2Semi standard non polar33892256
Cyclic GMP,1TMS,isomer #4C[Si](C)(C)N1C(N)=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(=O)(O)O[C@H]3[C@H]2O)C1=O3017.1Standard non polar33892256
Cyclic GMP,1TMS,isomer #4C[Si](C)(C)N1C(N)=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(=O)(O)O[C@H]3[C@H]2O)C1=O5533.6Standard polar33892256
Cyclic GMP,2TMS,isomer #1C[Si](C)(C)O[C@@H]1[C@@H]2OP(=O)(O[Si](C)(C)C)OC[C@H]2O[C@H]1N1C=NC2=C1N=C(N)[NH]C2=O3032.0Semi standard non polar33892256
Cyclic GMP,2TMS,isomer #1C[Si](C)(C)O[C@@H]1[C@@H]2OP(=O)(O[Si](C)(C)C)OC[C@H]2O[C@H]1N1C=NC2=C1N=C(N)[NH]C2=O3016.0Standard non polar33892256
Cyclic GMP,2TMS,isomer #1C[Si](C)(C)O[C@@H]1[C@@H]2OP(=O)(O[Si](C)(C)C)OC[C@H]2O[C@H]1N1C=NC2=C1N=C(N)[NH]C2=O4692.5Standard polar33892256
Cyclic GMP,2TMS,isomer #2C[Si](C)(C)NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(=O)(O)O[C@H]3[C@H]2O[Si](C)(C)C)C(=O)[NH]13029.8Semi standard non polar33892256
Cyclic GMP,2TMS,isomer #2C[Si](C)(C)NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(=O)(O)O[C@H]3[C@H]2O[Si](C)(C)C)C(=O)[NH]13041.1Standard non polar33892256
Cyclic GMP,2TMS,isomer #2C[Si](C)(C)NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(=O)(O)O[C@H]3[C@H]2O[Si](C)(C)C)C(=O)[NH]14966.4Standard polar33892256
Cyclic GMP,2TMS,isomer #3C[Si](C)(C)O[C@@H]1[C@@H]2OP(=O)(O)OC[C@H]2O[C@H]1N1C=NC2=C1N=C(N)N([Si](C)(C)C)C2=O3084.6Semi standard non polar33892256
Cyclic GMP,2TMS,isomer #3C[Si](C)(C)O[C@@H]1[C@@H]2OP(=O)(O)OC[C@H]2O[C@H]1N1C=NC2=C1N=C(N)N([Si](C)(C)C)C2=O3019.0Standard non polar33892256
Cyclic GMP,2TMS,isomer #3C[Si](C)(C)O[C@@H]1[C@@H]2OP(=O)(O)OC[C@H]2O[C@H]1N1C=NC2=C1N=C(N)N([Si](C)(C)C)C2=O5188.4Standard polar33892256
Cyclic GMP,2TMS,isomer #4C[Si](C)(C)NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(=O)(O[Si](C)(C)C)O[C@H]3[C@H]2O)C(=O)[NH]13021.2Semi standard non polar33892256
Cyclic GMP,2TMS,isomer #4C[Si](C)(C)NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(=O)(O[Si](C)(C)C)O[C@H]3[C@H]2O)C(=O)[NH]13045.3Standard non polar33892256
Cyclic GMP,2TMS,isomer #4C[Si](C)(C)NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(=O)(O[Si](C)(C)C)O[C@H]3[C@H]2O)C(=O)[NH]14577.5Standard polar33892256
Cyclic GMP,2TMS,isomer #5C[Si](C)(C)OP1(=O)OC[C@H]2O[C@@H](N3C=NC4=C3N=C(N)N([Si](C)(C)C)C4=O)[C@H](O)[C@@H]2O13095.7Semi standard non polar33892256
Cyclic GMP,2TMS,isomer #5C[Si](C)(C)OP1(=O)OC[C@H]2O[C@@H](N3C=NC4=C3N=C(N)N([Si](C)(C)C)C4=O)[C@H](O)[C@@H]2O13016.6Standard non polar33892256
Cyclic GMP,2TMS,isomer #5C[Si](C)(C)OP1(=O)OC[C@H]2O[C@@H](N3C=NC4=C3N=C(N)N([Si](C)(C)C)C4=O)[C@H](O)[C@@H]2O14862.1Standard polar33892256
Cyclic GMP,2TMS,isomer #6C[Si](C)(C)N(C1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(=O)(O)O[C@H]3[C@H]2O)C(=O)[NH]1)[Si](C)(C)C3020.7Semi standard non polar33892256
Cyclic GMP,2TMS,isomer #6C[Si](C)(C)N(C1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(=O)(O)O[C@H]3[C@H]2O)C(=O)[NH]1)[Si](C)(C)C3161.8Standard non polar33892256
Cyclic GMP,2TMS,isomer #6C[Si](C)(C)N(C1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(=O)(O)O[C@H]3[C@H]2O)C(=O)[NH]1)[Si](C)(C)C5018.2Standard polar33892256
Cyclic GMP,2TMS,isomer #7C[Si](C)(C)NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(=O)(O)O[C@H]3[C@H]2O)C(=O)N1[Si](C)(C)C3103.5Semi standard non polar33892256
Cyclic GMP,2TMS,isomer #7C[Si](C)(C)NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(=O)(O)O[C@H]3[C@H]2O)C(=O)N1[Si](C)(C)C3044.7Standard non polar33892256
Cyclic GMP,2TMS,isomer #7C[Si](C)(C)NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(=O)(O)O[C@H]3[C@H]2O)C(=O)N1[Si](C)(C)C5047.6Standard polar33892256
Cyclic GMP,3TMS,isomer #1C[Si](C)(C)NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(=O)(O[Si](C)(C)C)O[C@H]3[C@H]2O[Si](C)(C)C)C(=O)[NH]13025.4Semi standard non polar33892256
Cyclic GMP,3TMS,isomer #1C[Si](C)(C)NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(=O)(O[Si](C)(C)C)O[C@H]3[C@H]2O[Si](C)(C)C)C(=O)[NH]13037.3Standard non polar33892256
Cyclic GMP,3TMS,isomer #1C[Si](C)(C)NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(=O)(O[Si](C)(C)C)O[C@H]3[C@H]2O[Si](C)(C)C)C(=O)[NH]14251.1Standard polar33892256
Cyclic GMP,3TMS,isomer #2C[Si](C)(C)O[C@@H]1[C@@H]2OP(=O)(O[Si](C)(C)C)OC[C@H]2O[C@H]1N1C=NC2=C1N=C(N)N([Si](C)(C)C)C2=O3089.1Semi standard non polar33892256
Cyclic GMP,3TMS,isomer #2C[Si](C)(C)O[C@@H]1[C@@H]2OP(=O)(O[Si](C)(C)C)OC[C@H]2O[C@H]1N1C=NC2=C1N=C(N)N([Si](C)(C)C)C2=O3007.8Standard non polar33892256
Cyclic GMP,3TMS,isomer #2C[Si](C)(C)O[C@@H]1[C@@H]2OP(=O)(O[Si](C)(C)C)OC[C@H]2O[C@H]1N1C=NC2=C1N=C(N)N([Si](C)(C)C)C2=O4666.8Standard polar33892256
Cyclic GMP,3TMS,isomer #3C[Si](C)(C)O[C@@H]1[C@@H]2OP(=O)(O)OC[C@H]2O[C@H]1N1C=NC2=C1N=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]C2=O3042.5Semi standard non polar33892256
Cyclic GMP,3TMS,isomer #3C[Si](C)(C)O[C@@H]1[C@@H]2OP(=O)(O)OC[C@H]2O[C@H]1N1C=NC2=C1N=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]C2=O3152.7Standard non polar33892256
Cyclic GMP,3TMS,isomer #3C[Si](C)(C)O[C@@H]1[C@@H]2OP(=O)(O)OC[C@H]2O[C@H]1N1C=NC2=C1N=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]C2=O4563.4Standard polar33892256
Cyclic GMP,3TMS,isomer #4C[Si](C)(C)NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(=O)(O)O[C@H]3[C@H]2O[Si](C)(C)C)C(=O)N1[Si](C)(C)C3098.1Semi standard non polar33892256
Cyclic GMP,3TMS,isomer #4C[Si](C)(C)NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(=O)(O)O[C@H]3[C@H]2O[Si](C)(C)C)C(=O)N1[Si](C)(C)C3053.9Standard non polar33892256
Cyclic GMP,3TMS,isomer #4C[Si](C)(C)NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(=O)(O)O[C@H]3[C@H]2O[Si](C)(C)C)C(=O)N1[Si](C)(C)C4634.2Standard polar33892256
Cyclic GMP,3TMS,isomer #5C[Si](C)(C)OP1(=O)OC[C@H]2O[C@@H](N3C=NC4=C3N=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]C4=O)[C@H](O)[C@@H]2O13053.5Semi standard non polar33892256
Cyclic GMP,3TMS,isomer #5C[Si](C)(C)OP1(=O)OC[C@H]2O[C@@H](N3C=NC4=C3N=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]C4=O)[C@H](O)[C@@H]2O13155.1Standard non polar33892256
Cyclic GMP,3TMS,isomer #5C[Si](C)(C)OP1(=O)OC[C@H]2O[C@@H](N3C=NC4=C3N=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]C4=O)[C@H](O)[C@@H]2O14203.7Standard polar33892256
Cyclic GMP,3TMS,isomer #6C[Si](C)(C)NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(=O)(O[Si](C)(C)C)O[C@H]3[C@H]2O)C(=O)N1[Si](C)(C)C3109.9Semi standard non polar33892256
Cyclic GMP,3TMS,isomer #6C[Si](C)(C)NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(=O)(O[Si](C)(C)C)O[C@H]3[C@H]2O)C(=O)N1[Si](C)(C)C3050.0Standard non polar33892256
Cyclic GMP,3TMS,isomer #6C[Si](C)(C)NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(=O)(O[Si](C)(C)C)O[C@H]3[C@H]2O)C(=O)N1[Si](C)(C)C4278.4Standard polar33892256
Cyclic GMP,3TMS,isomer #7C[Si](C)(C)N(C1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(=O)(O)O[C@H]3[C@H]2O)C(=O)N1[Si](C)(C)C)[Si](C)(C)C3141.1Semi standard non polar33892256
Cyclic GMP,3TMS,isomer #7C[Si](C)(C)N(C1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(=O)(O)O[C@H]3[C@H]2O)C(=O)N1[Si](C)(C)C)[Si](C)(C)C3179.5Standard non polar33892256
Cyclic GMP,3TMS,isomer #7C[Si](C)(C)N(C1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(=O)(O)O[C@H]3[C@H]2O)C(=O)N1[Si](C)(C)C)[Si](C)(C)C4640.4Standard polar33892256
Cyclic GMP,4TMS,isomer #1C[Si](C)(C)O[C@@H]1[C@@H]2OP(=O)(O[Si](C)(C)C)OC[C@H]2O[C@H]1N1C=NC2=C1N=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]C2=O3086.6Semi standard non polar33892256
Cyclic GMP,4TMS,isomer #1C[Si](C)(C)O[C@@H]1[C@@H]2OP(=O)(O[Si](C)(C)C)OC[C@H]2O[C@H]1N1C=NC2=C1N=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]C2=O3160.9Standard non polar33892256
Cyclic GMP,4TMS,isomer #1C[Si](C)(C)O[C@@H]1[C@@H]2OP(=O)(O[Si](C)(C)C)OC[C@H]2O[C@H]1N1C=NC2=C1N=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]C2=O3906.3Standard polar33892256
Cyclic GMP,4TMS,isomer #2C[Si](C)(C)NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(=O)(O[Si](C)(C)C)O[C@H]3[C@H]2O[Si](C)(C)C)C(=O)N1[Si](C)(C)C3139.2Semi standard non polar33892256
Cyclic GMP,4TMS,isomer #2C[Si](C)(C)NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(=O)(O[Si](C)(C)C)O[C@H]3[C@H]2O[Si](C)(C)C)C(=O)N1[Si](C)(C)C3042.9Standard non polar33892256
Cyclic GMP,4TMS,isomer #2C[Si](C)(C)NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(=O)(O[Si](C)(C)C)O[C@H]3[C@H]2O[Si](C)(C)C)C(=O)N1[Si](C)(C)C3982.1Standard polar33892256
Cyclic GMP,4TMS,isomer #3C[Si](C)(C)O[C@@H]1[C@@H]2OP(=O)(O)OC[C@H]2O[C@H]1N1C=NC2=C1N=C(N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)C2=O3163.4Semi standard non polar33892256
Cyclic GMP,4TMS,isomer #3C[Si](C)(C)O[C@@H]1[C@@H]2OP(=O)(O)OC[C@H]2O[C@H]1N1C=NC2=C1N=C(N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)C2=O3197.6Standard non polar33892256
Cyclic GMP,4TMS,isomer #3C[Si](C)(C)O[C@@H]1[C@@H]2OP(=O)(O)OC[C@H]2O[C@H]1N1C=NC2=C1N=C(N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)C2=O4217.8Standard polar33892256
Cyclic GMP,4TMS,isomer #4C[Si](C)(C)OP1(=O)OC[C@H]2O[C@@H](N3C=NC4=C3N=C(N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)C4=O)[C@H](O)[C@@H]2O13171.8Semi standard non polar33892256
Cyclic GMP,4TMS,isomer #4C[Si](C)(C)OP1(=O)OC[C@H]2O[C@@H](N3C=NC4=C3N=C(N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)C4=O)[C@H](O)[C@@H]2O13181.0Standard non polar33892256
Cyclic GMP,4TMS,isomer #4C[Si](C)(C)OP1(=O)OC[C@H]2O[C@@H](N3C=NC4=C3N=C(N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)C4=O)[C@H](O)[C@@H]2O13921.5Standard polar33892256
Cyclic GMP,5TMS,isomer #1C[Si](C)(C)O[C@@H]1[C@@H]2OP(=O)(O[Si](C)(C)C)OC[C@H]2O[C@H]1N1C=NC2=C1N=C(N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)C2=O3208.7Semi standard non polar33892256
Cyclic GMP,5TMS,isomer #1C[Si](C)(C)O[C@@H]1[C@@H]2OP(=O)(O[Si](C)(C)C)OC[C@H]2O[C@H]1N1C=NC2=C1N=C(N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)C2=O3165.9Standard non polar33892256
Cyclic GMP,5TMS,isomer #1C[Si](C)(C)O[C@@H]1[C@@H]2OP(=O)(O[Si](C)(C)C)OC[C@H]2O[C@H]1N1C=NC2=C1N=C(N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)C2=O3679.0Standard polar33892256
Cyclic GMP,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H]2OP(=O)(O)OC[C@H]2O[C@H]1N1C=NC2=C1N=C(N)[NH]C2=O3287.4Semi standard non polar33892256
Cyclic GMP,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H]2OP(=O)(O)OC[C@H]2O[C@H]1N1C=NC2=C1N=C(N)[NH]C2=O3243.9Standard non polar33892256
Cyclic GMP,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H]2OP(=O)(O)OC[C@H]2O[C@H]1N1C=NC2=C1N=C(N)[NH]C2=O5359.1Standard polar33892256
Cyclic GMP,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OP1(=O)OC[C@H]2O[C@@H](N3C=NC4=C3N=C(N)[NH]C4=O)[C@H](O)[C@@H]2O13267.5Semi standard non polar33892256
Cyclic GMP,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OP1(=O)OC[C@H]2O[C@@H](N3C=NC4=C3N=C(N)[NH]C4=O)[C@H](O)[C@@H]2O13205.7Standard non polar33892256
Cyclic GMP,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OP1(=O)OC[C@H]2O[C@@H](N3C=NC4=C3N=C(N)[NH]C4=O)[C@H](O)[C@@H]2O15128.9Standard polar33892256
Cyclic GMP,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(=O)(O)O[C@H]3[C@H]2O)C(=O)[NH]13284.2Semi standard non polar33892256
Cyclic GMP,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(=O)(O)O[C@H]3[C@H]2O)C(=O)[NH]13257.8Standard non polar33892256
Cyclic GMP,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(=O)(O)O[C@H]3[C@H]2O)C(=O)[NH]15325.7Standard polar33892256
Cyclic GMP,1TBDMS,isomer #4CC(C)(C)[Si](C)(C)N1C(N)=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(=O)(O)O[C@H]3[C@H]2O)C1=O3323.9Semi standard non polar33892256
Cyclic GMP,1TBDMS,isomer #4CC(C)(C)[Si](C)(C)N1C(N)=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(=O)(O)O[C@H]3[C@H]2O)C1=O3228.5Standard non polar33892256
Cyclic GMP,1TBDMS,isomer #4CC(C)(C)[Si](C)(C)N1C(N)=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(=O)(O)O[C@H]3[C@H]2O)C1=O5446.8Standard polar33892256
Cyclic GMP,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H]2OP(=O)(O[Si](C)(C)C(C)(C)C)OC[C@H]2O[C@H]1N1C=NC2=C1N=C(N)[NH]C2=O3396.9Semi standard non polar33892256
Cyclic GMP,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H]2OP(=O)(O[Si](C)(C)C(C)(C)C)OC[C@H]2O[C@H]1N1C=NC2=C1N=C(N)[NH]C2=O3365.5Standard non polar33892256
Cyclic GMP,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H]2OP(=O)(O[Si](C)(C)C(C)(C)C)OC[C@H]2O[C@H]1N1C=NC2=C1N=C(N)[NH]C2=O4790.4Standard polar33892256
Cyclic GMP,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(=O)(O)O[C@H]3[C@H]2O[Si](C)(C)C(C)(C)C)C(=O)[NH]13404.3Semi standard non polar33892256
Cyclic GMP,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(=O)(O)O[C@H]3[C@H]2O[Si](C)(C)C(C)(C)C)C(=O)[NH]13450.5Standard non polar33892256
Cyclic GMP,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(=O)(O)O[C@H]3[C@H]2O[Si](C)(C)C(C)(C)C)C(=O)[NH]14933.5Standard polar33892256
Cyclic GMP,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H]2OP(=O)(O)OC[C@H]2O[C@H]1N1C=NC2=C1N=C(N)N([Si](C)(C)C(C)(C)C)C2=O3486.7Semi standard non polar33892256
Cyclic GMP,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H]2OP(=O)(O)OC[C@H]2O[C@H]1N1C=NC2=C1N=C(N)N([Si](C)(C)C(C)(C)C)C2=O3430.3Standard non polar33892256
Cyclic GMP,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H]2OP(=O)(O)OC[C@H]2O[C@H]1N1C=NC2=C1N=C(N)N([Si](C)(C)C(C)(C)C)C2=O5154.4Standard polar33892256
Cyclic GMP,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(=O)(O[Si](C)(C)C(C)(C)C)O[C@H]3[C@H]2O)C(=O)[NH]13390.8Semi standard non polar33892256
Cyclic GMP,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(=O)(O[Si](C)(C)C(C)(C)C)O[C@H]3[C@H]2O)C(=O)[NH]13409.6Standard non polar33892256
Cyclic GMP,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(=O)(O[Si](C)(C)C(C)(C)C)O[C@H]3[C@H]2O)C(=O)[NH]14638.4Standard polar33892256
Cyclic GMP,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)OP1(=O)OC[C@H]2O[C@@H](N3C=NC4=C3N=C(N)N([Si](C)(C)C(C)(C)C)C4=O)[C@H](O)[C@@H]2O13478.0Semi standard non polar33892256
Cyclic GMP,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)OP1(=O)OC[C@H]2O[C@@H](N3C=NC4=C3N=C(N)N([Si](C)(C)C(C)(C)C)C4=O)[C@H](O)[C@@H]2O13381.2Standard non polar33892256
Cyclic GMP,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)OP1(=O)OC[C@H]2O[C@@H](N3C=NC4=C3N=C(N)N([Si](C)(C)C(C)(C)C)C4=O)[C@H](O)[C@@H]2O14877.0Standard polar33892256
Cyclic GMP,2TBDMS,isomer #6CC(C)(C)[Si](C)(C)N(C1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(=O)(O)O[C@H]3[C@H]2O)C(=O)[NH]1)[Si](C)(C)C(C)(C)C3417.5Semi standard non polar33892256
Cyclic GMP,2TBDMS,isomer #6CC(C)(C)[Si](C)(C)N(C1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(=O)(O)O[C@H]3[C@H]2O)C(=O)[NH]1)[Si](C)(C)C(C)(C)C3535.6Standard non polar33892256
Cyclic GMP,2TBDMS,isomer #6CC(C)(C)[Si](C)(C)N(C1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(=O)(O)O[C@H]3[C@H]2O)C(=O)[NH]1)[Si](C)(C)C(C)(C)C4881.1Standard polar33892256
Cyclic GMP,2TBDMS,isomer #7CC(C)(C)[Si](C)(C)NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(=O)(O)O[C@H]3[C@H]2O)C(=O)N1[Si](C)(C)C(C)(C)C3507.1Semi standard non polar33892256
Cyclic GMP,2TBDMS,isomer #7CC(C)(C)[Si](C)(C)NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(=O)(O)O[C@H]3[C@H]2O)C(=O)N1[Si](C)(C)C(C)(C)C3455.3Standard non polar33892256
Cyclic GMP,2TBDMS,isomer #7CC(C)(C)[Si](C)(C)NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(=O)(O)O[C@H]3[C@H]2O)C(=O)N1[Si](C)(C)C(C)(C)C4898.2Standard polar33892256
Cyclic GMP,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(=O)(O[Si](C)(C)C(C)(C)C)O[C@H]3[C@H]2O[Si](C)(C)C(C)(C)C)C(=O)[NH]13553.5Semi standard non polar33892256
Cyclic GMP,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(=O)(O[Si](C)(C)C(C)(C)C)O[C@H]3[C@H]2O[Si](C)(C)C(C)(C)C)C(=O)[NH]13573.9Standard non polar33892256
Cyclic GMP,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(=O)(O[Si](C)(C)C(C)(C)C)O[C@H]3[C@H]2O[Si](C)(C)C(C)(C)C)C(=O)[NH]14402.5Standard polar33892256
Cyclic GMP,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H]2OP(=O)(O[Si](C)(C)C(C)(C)C)OC[C@H]2O[C@H]1N1C=NC2=C1N=C(N)N([Si](C)(C)C(C)(C)C)C2=O3648.2Semi standard non polar33892256
Cyclic GMP,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H]2OP(=O)(O[Si](C)(C)C(C)(C)C)OC[C@H]2O[C@H]1N1C=NC2=C1N=C(N)N([Si](C)(C)C(C)(C)C)C2=O3548.5Standard non polar33892256
Cyclic GMP,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H]2OP(=O)(O[Si](C)(C)C(C)(C)C)OC[C@H]2O[C@H]1N1C=NC2=C1N=C(N)N([Si](C)(C)C(C)(C)C)C2=O4728.5Standard polar33892256
Cyclic GMP,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H]2OP(=O)(O)OC[C@H]2O[C@H]1N1C=NC2=C1N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]C2=O3574.6Semi standard non polar33892256
Cyclic GMP,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H]2OP(=O)(O)OC[C@H]2O[C@H]1N1C=NC2=C1N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]C2=O3710.1Standard non polar33892256
Cyclic GMP,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H]2OP(=O)(O)OC[C@H]2O[C@H]1N1C=NC2=C1N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]C2=O4558.5Standard polar33892256
Cyclic GMP,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(=O)(O)O[C@H]3[C@H]2O[Si](C)(C)C(C)(C)C)C(=O)N1[Si](C)(C)C(C)(C)C3684.1Semi standard non polar33892256
Cyclic GMP,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(=O)(O)O[C@H]3[C@H]2O[Si](C)(C)C(C)(C)C)C(=O)N1[Si](C)(C)C(C)(C)C3634.0Standard non polar33892256
Cyclic GMP,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(=O)(O)O[C@H]3[C@H]2O[Si](C)(C)C(C)(C)C)C(=O)N1[Si](C)(C)C(C)(C)C4611.4Standard polar33892256
Cyclic GMP,3TBDMS,isomer #5CC(C)(C)[Si](C)(C)OP1(=O)OC[C@H]2O[C@@H](N3C=NC4=C3N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]C4=O)[C@H](O)[C@@H]2O13541.3Semi standard non polar33892256
Cyclic GMP,3TBDMS,isomer #5CC(C)(C)[Si](C)(C)OP1(=O)OC[C@H]2O[C@@H](N3C=NC4=C3N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]C4=O)[C@H](O)[C@@H]2O13669.1Standard non polar33892256
Cyclic GMP,3TBDMS,isomer #5CC(C)(C)[Si](C)(C)OP1(=O)OC[C@H]2O[C@@H](N3C=NC4=C3N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]C4=O)[C@H](O)[C@@H]2O14301.2Standard polar33892256
Cyclic GMP,3TBDMS,isomer #6CC(C)(C)[Si](C)(C)NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(=O)(O[Si](C)(C)C(C)(C)C)O[C@H]3[C@H]2O)C(=O)N1[Si](C)(C)C(C)(C)C3662.1Semi standard non polar33892256
Cyclic GMP,3TBDMS,isomer #6CC(C)(C)[Si](C)(C)NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(=O)(O[Si](C)(C)C(C)(C)C)O[C@H]3[C@H]2O)C(=O)N1[Si](C)(C)C(C)(C)C3577.1Standard non polar33892256
Cyclic GMP,3TBDMS,isomer #6CC(C)(C)[Si](C)(C)NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(=O)(O[Si](C)(C)C(C)(C)C)O[C@H]3[C@H]2O)C(=O)N1[Si](C)(C)C(C)(C)C4352.9Standard polar33892256
Cyclic GMP,3TBDMS,isomer #7CC(C)(C)[Si](C)(C)N(C1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(=O)(O)O[C@H]3[C@H]2O)C(=O)N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3681.2Semi standard non polar33892256
Cyclic GMP,3TBDMS,isomer #7CC(C)(C)[Si](C)(C)N(C1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(=O)(O)O[C@H]3[C@H]2O)C(=O)N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3723.7Standard non polar33892256
Cyclic GMP,3TBDMS,isomer #7CC(C)(C)[Si](C)(C)N(C1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(=O)(O)O[C@H]3[C@H]2O)C(=O)N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C4566.9Standard polar33892256
Cyclic GMP,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H]2OP(=O)(O[Si](C)(C)C(C)(C)C)OC[C@H]2O[C@H]1N1C=NC2=C1N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]C2=O3717.9Semi standard non polar33892256
Cyclic GMP,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H]2OP(=O)(O[Si](C)(C)C(C)(C)C)OC[C@H]2O[C@H]1N1C=NC2=C1N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]C2=O3818.1Standard non polar33892256
Cyclic GMP,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H]2OP(=O)(O[Si](C)(C)C(C)(C)C)OC[C@H]2O[C@H]1N1C=NC2=C1N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]C2=O4108.1Standard polar33892256
Cyclic GMP,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(=O)(O[Si](C)(C)C(C)(C)C)O[C@H]3[C@H]2O[Si](C)(C)C(C)(C)C)C(=O)N1[Si](C)(C)C(C)(C)C3836.4Semi standard non polar33892256
Cyclic GMP,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(=O)(O[Si](C)(C)C(C)(C)C)O[C@H]3[C@H]2O[Si](C)(C)C(C)(C)C)C(=O)N1[Si](C)(C)C(C)(C)C3725.5Standard non polar33892256
Cyclic GMP,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(=O)(O[Si](C)(C)C(C)(C)C)O[C@H]3[C@H]2O[Si](C)(C)C(C)(C)C)C(=O)N1[Si](C)(C)C(C)(C)C4174.7Standard polar33892256
Cyclic GMP,4TBDMS,isomer #3CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H]2OP(=O)(O)OC[C@H]2O[C@H]1N1C=NC2=C1N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C2=O3865.3Semi standard non polar33892256
Cyclic GMP,4TBDMS,isomer #3CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H]2OP(=O)(O)OC[C@H]2O[C@H]1N1C=NC2=C1N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C2=O3882.4Standard non polar33892256
Cyclic GMP,4TBDMS,isomer #3CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H]2OP(=O)(O)OC[C@H]2O[C@H]1N1C=NC2=C1N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C2=O4283.5Standard polar33892256
Cyclic GMP,4TBDMS,isomer #4CC(C)(C)[Si](C)(C)OP1(=O)OC[C@H]2O[C@@H](N3C=NC4=C3N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C4=O)[C@H](O)[C@@H]2O13825.3Semi standard non polar33892256
Cyclic GMP,4TBDMS,isomer #4CC(C)(C)[Si](C)(C)OP1(=O)OC[C@H]2O[C@@H](N3C=NC4=C3N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C4=O)[C@H](O)[C@@H]2O13816.0Standard non polar33892256
Cyclic GMP,4TBDMS,isomer #4CC(C)(C)[Si](C)(C)OP1(=O)OC[C@H]2O[C@@H](N3C=NC4=C3N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C4=O)[C@H](O)[C@@H]2O14096.9Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Cyclic GMP GC-MS (4 TMS)splash10-001i-2972000000-80320c485cef8d6d91ad2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Cyclic GMP GC-MS (Non-derivatized)splash10-001i-2972000000-80320c485cef8d6d91ad2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cyclic GMP GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f76-3901000000-c970aad6713a547b2d8f2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cyclic GMP GC-MS (1 TMS) - 70eV, Positivesplash10-00di-4590100000-edbc82f84eca5a64f5a52017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cyclic GMP GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cyclic GMP GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Cyclic GMP LC-ESI-QTOF , negative-QTOFsplash10-0uec-2904000000-85af5865e64af24e76912017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cyclic GMP Linear Ion Trap , negative-QTOFsplash10-0udi-0904000000-e34bb3204af3b18ddf112017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cyclic GMP Linear Ion Trap , negative-QTOFsplash10-0udj-0908000000-35925bce602ee60e24ee2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cyclic GMP Linear Ion Trap , negative-QTOFsplash10-0udj-0904000000-93fabfb961527e02671e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cyclic GMP Linear Ion Trap , negative-QTOFsplash10-0udj-0907000000-60b56b2fcc437a04a7b82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cyclic GMP Linear Ion Trap , negative-QTOFsplash10-0udj-0908000000-16c413e42a41fa5e72622017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cyclic GMP , negative-QTOFsplash10-0udl-3904000000-051a745d5db4f607a9352017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cyclic GMP LC-ESI-QTOF , positive-QTOFsplash10-0udi-0901000000-a2a6721a5a98c3d3e9452017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cyclic GMP Linear Ion Trap , positive-QTOFsplash10-0udj-0907000000-ae3d3b4dfb6aefdd34c32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cyclic GMP Linear Ion Trap , positive-QTOFsplash10-0udj-0904000000-fd635f17953dbbff039b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cyclic GMP Linear Ion Trap , positive-QTOFsplash10-0udi-0902000000-36d8b1a240f9f64718862017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cyclic GMP Linear Ion Trap , positive-QTOFsplash10-0002-0009000000-4c75be42ba8dbd671bbf2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cyclic GMP Linear Ion Trap , positive-QTOFsplash10-0002-0009000000-06ee1dc93418cde4fe392017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cyclic GMP Linear Ion Trap , positive-QTOFsplash10-0udi-0900000000-db6612a4a4b92db515072017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cyclic GMP Linear Ion Trap , positive-QTOFsplash10-0udi-0900000000-8455683aa1bc0141dd382017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cyclic GMP Linear Ion Trap , positive-QTOFsplash10-0udi-0900000000-196c267f58b468d3a8f52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cyclic GMP Linear Ion Trap , positive-QTOFsplash10-0002-0009000000-7637808812023bf3fb332017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cyclic GMP Linear Ion Trap , positive-QTOFsplash10-0002-0009000000-34c09019debbbd2ef2a62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cyclic GMP Linear Ion Trap , positive-QTOFsplash10-0002-0009000000-db049b28da12291887ce2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclic GMP 10V, Positive-QTOFsplash10-0udi-0904000000-65ab088e129c01a9b1402015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclic GMP 20V, Positive-QTOFsplash10-0udi-0900000000-fc45e23a1d622d9a68482015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclic GMP 40V, Positive-QTOFsplash10-0udr-0900000000-d7d3bc38b1c32086753e2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclic GMP 10V, Negative-QTOFsplash10-0f6x-1709000000-881760c573673e832db82015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclic GMP 20V, Negative-QTOFsplash10-0udi-2900000000-f74b8ec55fbea3fdf8cd2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclic GMP 40V, Negative-QTOFsplash10-003u-9600000000-d7f00c8f8cec474c73042015-09-15Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Nucleus
  • Golgi apparatus
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Locations
  • Kidney
  • Platelet
  • Smooth Muscle
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0055 +/- 0.0003 uMAdult (>18 years old)MaleNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0024 +/- 0.0005 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0035 +/- 0.0003 uMAdult (>18 years old)BothSildenafil-induced headache details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease References
Headache
  1. Kruuse C, Frandsen E, Schifter S, Thomsen LL, Birk S, Olesen J: Plasma levels of cAMP, cGMP and CGRP in sildenafil-induced headache. Cephalalgia. 2004 Jul;24(7):547-53. [PubMed:15196297 ]
Associated OMIM IDsNone
DrugBank IDDB02315
Phenol Explorer Compound IDNot Available
FooDB IDFDB030764
KNApSAcK IDC00019673
Chemspider ID22734
KEGG Compound IDC00942
BioCyc IDNot Available
BiGG ID1485267
Wikipedia LinkCyclic guanosine monophosphate
METLIN ID6152
PubChem Compound24316
PDB IDNot Available
ChEBI ID16356
Food Biomarker OntologyNot Available
VMH ID35CGMP
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceSekhar, 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.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Mashayekhi F, Aghahoseini F, Rezaie A, Zamani MJ, Khorasani R, Abdollahi M: Alteration of cyclic nucleotides levels and oxidative stress in saliva of human subjects with periodontitis. J Contemp Dent Pract. 2005 Nov 15;6(4):46-53. [PubMed:16299606 ]
  2. Rudman D, O'Brien MS, McKinney AS, Hoffman JC Jr, Patterson JH: Observations on the cyclic nucleotide concentrations in human cerebrospinal fluid. J Clin Endocrinol Metab. 1976 Jun;42(6):1088-97. [PubMed:180045 ]
  3. Martina V, Benso A, Gigliardi VR, Masha A, Origlia C, Granata R, Ghigo E: Short-term dehydroepiandrosterone treatment increases platelet cGMP production in elderly male subjects. Clin Endocrinol (Oxf). 2006 Mar;64(3):260-4. [PubMed:16487434 ]
  4. Kotikoski H, Moilanen E, Vapaatalo H, Aine E: Biochemical markers of the L-arginine-nitric oxide pathway in the aqueous humour in glaucoma patients. Acta Ophthalmol Scand. 2002 Apr;80(2):191-5. [PubMed:11952488 ]
  5. Young DV, Cochran ED, Dhawan V, Earl RA, Ellis JL, Garvey DS, Janero DR, Khanapure SP, Letts LG, Melim TL, Murty MG, Shumway MJ, Wey SJ, Zemtseva IS, Selig WM: A comparison of the cyclooxygenase inhibitor-NO donors (CINOD), NMI-1182 and AZD3582, using in vitro biochemical and pharmacological methods. Biochem Pharmacol. 2005 Nov 1;70(9):1343-51. [PubMed:16168964 ]
  6. Dobrzynski E, Montanari D, Agata J, Zhu J, Chao J, Chao L: Adrenomedullin improves cardiac function and prevents renal damage in streptozotocin-induced diabetic rats. Am J Physiol Endocrinol Metab. 2002 Dec;283(6):E1291-8. [PubMed:12424108 ]
  7. Willoughby SR, Stewart S, Chirkov YY, Kennedy JA, Holmes AS, Horowitz JD: Beneficial clinical effects of perhexiline in patients with stable angina pectoris and acute coronary syndromes are associated with potentiation of platelet responsiveness to nitric oxide. Eur Heart J. 2002 Dec;23(24):1946-54. [PubMed:12473257 ]
  8. Barani J, Gottsater A, Mattiasson I, Lindblad B: Platelet and leukocyte activation during aortoiliac angiography and angioplasty. Eur J Vasc Endovasc Surg. 2002 Mar;23(3):220-5. [PubMed:11914008 ]
  9. Schiessl B, Strasburger CJ, Bidlingmaier M, Spannagl M, Ugele B, Kainer F: Decreasing resistance in the maternal uterine and peripheral arterial system is apparently unrelated to plasma and urinary levels of nitrite/nitrate and cyclic-guanosinmonophosohate during the course of normal pregnancies. J Perinat Med. 2003;31(4):281-6. [PubMed:12951882 ]
  10. Bai X, Wang H, Li Z, Liu K: Correlation between blood cAMP, cGMP levels and traumatic severity in the patients with acute trauma and its clinical significance. J Huazhong Univ Sci Technolog Med Sci. 2004;24(1):68-70. [PubMed:15165120 ]
  11. Beltowski J, Jamroz A, Borkowska E: [Heme oxygenase and carbon monoxide in the physiology and pathology of the cardiovascular system]. Postepy Hig Med Dosw (Online). 2004 Mar 3;58:83-99. [PubMed:15069378 ]
  12. Peracchi M, Lombardi L, Maiolo AT, Bamonti-Catena F, Toschi V, Chiorboli O, Mozzana R, Polli EE: Plasma and urine cyclic nucleotide levels in patients with acute and chronic leukemia. Blood. 1983 Mar;61(3):429-34. [PubMed:6297636 ]
  13. Ilecka J: Decreased cerebrospinal fluid cGMP levels in patients with amyotrophic lateral sclerosis. J Neural Transm (Vienna). 2004 Feb;111(2):167-72. Epub 2003 Dec 12. [PubMed:14767719 ]
  14. Hunter KA, Singh GJ, Simpkins CO: Cyclic gmp is a measure of physiologic stress. J Natl Med Assoc. 2001 Jul-Aug;93(7-8):256-62. [PubMed:11491275 ]
  15. Zhang H, Zheng RL, Xu CY: [Relationships between lipid peroxidation or cyclic nucleotides and motility in human asthenozoosperm and normosperm]. Shi Yan Sheng Wu Xue Bao. 1998 Dec;31(4):341-6. [PubMed:12016956 ]
  16. Engelhardt T, Galley HF, MacLennan FM, Webster NR: Saliva cyclic GMP increases during anaesthesia. Br J Anaesth. 2002 Oct;89(4):635-7. [PubMed:12393367 ]
  17. Galassi F, Renieri G, Sodi A, Ucci F, Vannozzi L, Masini E: Nitric oxide proxies and ocular perfusion pressure in primary open angle glaucoma. Br J Ophthalmol. 2004 Jun;88(6):757-60. [PubMed:15148207 ]
  18. Zhao L, Gray L, Leonardi-Bee J, Weaver CS, Heptinstall S, Bath PM: Effect of aspirin, clopidogrel and dipyridamole on soluble markers of vascular function in normal volunteers and patients with prior ischaemic stroke. Platelets. 2006 Mar;17(2):100-4. [PubMed:16421011 ]
  19. Martina V, Origlia C, Bruno GA, Messina M, Ferri M, Pescarmona GP: Serum DHEAS levels correlate with platelet cGMP in normal women. J Endocrinol Invest. 2001 Nov;24(10):RC28-30. [PubMed:11765058 ]
  20. St Pierre MV, Schlenker T, Dufour JF, Jefferson DM, Fitz JG, Arias IM: Stimulation of cyclic guanosine monophosphate production by natriuretic peptide in human biliary cells. Gastroenterology. 1998 Apr;114(4):782-90. [PubMed:9516399 ]

Only showing the first 10 proteins. There are 46 proteins in total.

Enzymes

General function:
Involved in 3',5'-cyclic-nucleotide phosphodiesterase activity
Specific function:
Participates in processes of transmission and amplification of the visual signal. cGMP-PDEs are the effector molecules in G-protein-mediated phototransduction in vertebrate rods and cones.
Gene Name:
PDE6H
Uniprot ID:
Q13956
Molecular weight:
9074.36
General function:
Involved in catalytic activity
Specific function:
Cyclic nucleotide phosphodiesterase with a dual-specificity for the second messengers cAMP and cGMP, which are key regulators of many important physiological processes. Has a higher affinity for cGMP than for cAMP.
Gene Name:
PDE1A
Uniprot ID:
P54750
Molecular weight:
61251.38
Reactions
Cyclic GMP + Water → Guanosine monophosphatedetails
General function:
Involved in catalytic activity
Specific function:
Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes. May be involved in maintaining basal levels of the cyclic nucleotide and/or in the cAMP regulation of germ cell development.
Gene Name:
PDE8A
Uniprot ID:
O60658
Molecular weight:
86047.88
Reactions
Cyclic GMP + Water → Guanosine monophosphatedetails
General function:
Involved in catalytic activity
Specific function:
Cyclic nucleotide phosphodiesterase with a dual-specificity for the second messengers cAMP and cGMP, which are key regulators of many important physiological processes. Has a preference for cGMP as a substrate.
Gene Name:
PDE1B
Uniprot ID:
Q01064
Molecular weight:
61379.235
Reactions
Cyclic GMP + Water → Guanosine monophosphatedetails
General function:
Involved in catalytic activity
Specific function:
Cyclic nucleotide phosphodiesterase with a dual-specificity for the second messengers cAMP and cGMP, which are key regulators of many important physiological processes. May play a role in fat metabolism. Regulates cAMP binding of RAPGEF3. Through simultaneous binding to RAPGEF3 and PIK3R6 assembles a signaling complex in which the PI3K gamma complex is activated by RAPGEF3 and which is involved in angiogenesis.
Gene Name:
PDE3B
Uniprot ID:
Q13370
Molecular weight:
124332.145
Reactions
Cyclic GMP + Water → Guanosine monophosphatedetails
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
PDE6C
Uniprot ID:
P51160
Molecular weight:
99146.095
Reactions
Cyclic GMP + Water → Guanosine monophosphatedetails
General function:
Involved in 3',5'-cyclic-AMP phosphodiesterase activity
Specific function:
Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes. May have a role in muscle signal transduction.
Gene Name:
PDE7A
Uniprot ID:
Q13946
Molecular weight:
55504.475
Reactions
Cyclic GMP + Water → Guanosine monophosphatedetails
General function:
Involved in catalytic activity
Specific function:
Cyclic nucleotide phosphodiesterase with a dual-specificity for the second messengers cAMP and cGMP, which are key regulators of many important physiological processes (By similarity).
Gene Name:
PDE3A
Uniprot ID:
Q14432
Molecular weight:
124978.06
Reactions
Cyclic GMP + Water → Guanosine monophosphatedetails
General function:
Involved in catalytic activity
Specific function:
Plays a role in signal transduction by regulating the intracellular concentration of cyclic nucleotides. Can hydrolyze both cAMP and cGMP, but has higher affinity for cAMP and is more efficient with cAMP as substrate.
Gene Name:
PDE10A
Uniprot ID:
Q9Y233
Molecular weight:
89388.7
Reactions
Cyclic GMP + Water → Guanosine monophosphatedetails
General function:
Involved in catalytic activity
Specific function:
Cyclic nucleotide phosphodiesterase with a dual-specificity for the second messengers cAMP and cGMP, which are key regulators of many important physiological processes. Has a high affinity for both cAMP and cGMP.
Gene Name:
PDE1C
Uniprot ID:
Q14123
Molecular weight:
72207.775
Reactions
Cyclic GMP + Water → Guanosine monophosphatedetails

Only showing the first 10 proteins. There are 46 proteins in total.