Guanosine 3′,5′-cyclic monophosphate - Moligand™, ≥98% , Activator of CNGA1;Activator of CNGA2;Activator of CNGA3;Activator of HCN2;Activator of phosphodiesterase 2A;Inhibitor of phosphodiesterase 3A;Inhibitor of phosphodiesterase 3B, CAS No.7665-99-8, Activator of CNGA1;Activator of CNGA2;Activator of CNGA3;Activator of HCN2;Activator of phosphodiesterase 2A;Inhibitor of phosphodiesterase 3A;Inhibitor of phosphodiesterase 3B

CAS: 7665-99-8 Cat. No.: G349525 Molecular Weight: 345.21 EC Number: 231-641-6

GRADE & PURITY Moligand™, ≥98%

Synonyms

3',5'-cGMP | 35G | cyclic gmp | EINECS 231-641-6 | 2-amino-9-[(2S,4aR,6R,7R,7aS)-2,7-dihydroxy-2-oxidotetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl]-1,9-dihydro-6H-purin-6-one | Cyclic guanosine 3',5'-monophosphate | Epitope ID:149170 | GMP, Cyclic

Storage

Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Overview

Guanosine 3',5'-cyclic monophosphate is an important second messenger which is a major intracellular mediator of extracellular signals such as nitric oxide and natriuretic peptides. Interacts with three types of intracellular receptor proteins: cGMP-dependent protein kinases, cGMP-regulated channels, and cGMP-regulated cyclic nucleotide phosphodiesterases.

Specifications

Synonyms

3', 5'-cGMP | 35G | cyclic gmp | EINECS 231-641-6 | 2-amino-9-[(2S, 4aR, 6R, 7R, 7aS)-2, 7-dihydroxy-2-oxidotetrahydro-4H-furo[3, 2-d][1, 3, 2]dioxaphosphinin-6-yl]-1, 9-dihydro-6H-purin-6-one | Cyclic guanosine 3', 5'-monophosphate | Epitope ID:149170 | GMP, Cyclic

Specifications & Purity

Moligand™, ≥98%

Storage

Store at -20°C, Argon charged

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Action Type

ACTIVATOR, INHIBITOR

Mechanism of action

Activator of CNGA1;Activator of CNGA2;Activator of CNGA3;Activator of HCN2;Activator of phosphodiesterase 2A;Inhibitor of phosphodiesterase 3A;Inhibitor of phosphodiesterase 3B

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 504773232
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504773232
• Canonical Smiles: C1C2C(C(C(O2)N3C=NC4=C3N=C(NC4=O)N)O)OP(=O)(O1)O
• IUPAC Name: 9-[(4aR,6R,7R,7aS)-2,7-dihydroxy-2-oxo-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl]-2-amino-1H-purin-6-one
• InChIKey: ZOOGRGPOEVQQDX-UUOKFMHZSA-N
• 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
• Isomeric SMILES: C1[C@@H]2[C@H]([C@H]([C@@H](O2)N3C=NC4=C3N=C(NC4=O)N)O)OP(=O)(O1)O
• WGK Germany: 3
• Molecular Weight: 345.21
• Reaxy-Rn: 24731030
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=24731030&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Nucleosides, nucleotides, and analogues
    • Class Purine nucleotides
      • Subclass Cyclic purine nucleotides

• Kingdom: Organic compounds
• Superclass: Nucleosides, nucleotides, and analogues
• Class: Purine nucleotides
• Subclass: Cyclic purine nucleotides
• Intermediate Tree Nodes: Not available
• Direct Parent: 3',5'-cyclic purine nucleotides
• Alternative Parents: Pentose phosphates Glycosylamines 6-oxopurines Hypoxanthines Monosaccharide phosphates Aminopyrimidines and derivatives Pyrimidones N-substituted imidazoles Organic phosphoric acids and derivatives Vinylogous amides Tetrahydrofurans Heteroaromatic compounds Secondary alcohols Azacyclic compounds Oxacyclic compounds Primary amines Hydrocarbon derivatives Organopnictogen compounds Organic oxides
• Molecular Framework: Aromatic heteropolycyclic compounds
• 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
• Description: This compound 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.
• External Descriptors: 3',5'-Cyclic nuclcleotides

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

CNGA3 Tchem Cyclic nucleotide-gated cation channel alpha-3 (1 Activities)

Discover Target: CNGA3

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

PDE3A Tclin cGMP-inhibited 3',5'-cyclic phosphodiesterase A (0 Activities)

Discover Target: PDE3A

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

PDE3B Tclin cGMP-inhibited 3',5'-cyclic phosphodiesterase B (0 Activities)

Discover Target: PDE3B

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

PDE2A Tclin cGMP-dependent 3',5'-cyclic phosphodiesterase (0 Activities)

Discover Target: PDE2A

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

CNGA1 Tchem cGMP-gated cation channel alpha-1 (0 Activities)

Discover Target: CNGA1

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

CNGA2 Tchem Cyclic nucleotide-gated olfactory channel (0 Activities)

Discover Target: CNGA2

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

HCN2 Tclin Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 2 (1 Activities)

Discover Target: HCN2

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

PDE3B Tclin Phosphodiesterase 3B (312 Activities)

Discover Target: PDE3B

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ABCC4 Tchem Multidrug resistance-associated protein 4 (785 Activities)

Discover Target: ABCC4

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SLC22A7 Tbio Solute carrier family 22 member 7 (39 Activities)

Discover Target: SLC22A7

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ABCC5 Tchem Multidrug resistance-associated protein 5 (50 Activities)

Discover Target: ABCC5

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ABCC11 Tbio ATP-binding cassette sub-family C member 11 (24 Activities)

Discover Target: ABCC11

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PDE3A Tclin Phosphodiesterase 3 (1749 Activities)

Discover Target: PDE3A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Slc22a6 Solute carrier family 22 member 6 (141 Activities)

Discover Target: Slc22a6

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Solubility: 50 mg/mL of 1% sodium bicarbonate
• Sensitivity: Moisture sensitive
• Boil Point(°C): 480.00° C (Predicted)
• Melt Point(°C): 90.27° C (Predicted)
• Molecular Weight: 345.210 g/mol
• XLogP3: -3.400
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 1
• Exact Mass: 345.047 Da
• Monoisotopic Mass: 345.047 Da
• Topological Polar Surface Area: 171.000 Ų
• Heavy Atom Count: 23
• Formal Charge: 0
• Complexity: 616.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 4
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Chenghao Huang, Fei Huang, Xuke Wang, Dongru Wang, Jiawei Wang, Xinhua Zhan.  (2024)  Regulation mechanism of exogenous nitric oxide on phenanthrene uptake by ryegrass roots.  PLANT PHYSIOLOGY AND BIOCHEMISTRY,      [PMID:39395225] [10.1016/j.plaphy.2024.109185]