3',5'-cyclic IMP (YMDB00453)

Identification

YMDB ID

YMDB00453

Name

3',5'-cyclic IMP

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

3',5'-cyclic IMP, also known as cyclic imp, 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. 3',5'-cyclic IMP is an extremely weak basic (essentially neutral) compound (based on its pKa). 3',5'-cyclic IMP may be a unique S. cerevisiae (yeast) metabolite.

Structure

MOL SDF PDB SMILES InChI

Synonyms

3',5'-Cyclic IMP
cyclic IMP
Inosine 3',5'-cyclic monophosphate
inosine cyclic 3',5'-(hydrogen phosphate)
Inosine 3',5'-cyclic monophosphoric acid
Inosine cyclic 3',5'-(hydrogen phosphoric acid)

CAS number

3545-76-4

Weight

Average: 330.1907
Monoisotopic: 330.036535238

InChI Key

DMJWGQPYNRPLGA-KQYNXXCUSA-N

InChI

InChI=1S/C10H11N4O7P/c15-6-7-4(1-19-22(17,18)21-7)20-10(6)14-3-13-5-8(14)11-2-12-9(5)16/h2-4,6-7,10,15H,1H2,(H,17,18)(H,11,12,16)/t4-,6-,7-,10-/m1/s1

IUPAC Name

(4aR,6R,7R,7aS)-2,7-dihydroxy-6-(6-hydroxy-9H-purin-9-yl)-hexahydro-2λ⁵-furo[3,2-d][1,3,2]dioxaphosphinin-2-one

Traditional IUPAC Name

cyclic imp

Chemical Formula

C₁₀H₁₁N₄O₇P

SMILES

O[C@H]1[C@@H](O[C@@H]2COP(O)(=O)O[C@@H]12)N1C=NC2=C(O)N=CN=C12

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.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleotides

Sub Class

Cyclic purine nucleotides

Direct Parent

3',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
Pyrimidone
Monosaccharide
N-substituted imidazole
Organic phosphoric acid derivative
Pyrimidine
Azole
Imidazole
Heteroaromatic compound
Vinylogous amide
Tetrahydrofuran
Secondary alcohol
Organoheterocyclic compound
Azacycle
Oxacycle
Alcohol
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

3',5'-cyclic purine nucleotide (CHEBI:27541 )
nucleoside 3',5'-cyclic phosphate (CHEBI:27541 )
3',5'-Cyclic nuclcleotides (C00943 )

Physical Properties

State

Not Available

Charge

Melting point

Not Available

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	4.12 g/L	ALOGPS
logP	-2.1	ALOGPS
logP	-2.4	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	1.84	ChemAxon
pKa (Strongest Basic)	0.056	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	149.05 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	67.57 m³·mol⁻¹	ChemAxon
Polarizability	27.78 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

cytoplasm

Organoleptic Properties

Not Available

SMPDB Pathways

Not Available

KEGG Pathways

Not Available

SMPDB Reactions

Not Available

KEGG Reactions

water + 3',5'-cyclic IMP → Inosinic acid + hydron

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0905000000-9909d05a8bea0ddc163e	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0900000000-8b8b01340e24edbf66b7	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01p9-0900000000-2aaf783de273a2200c1e	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004r-1709000000-e75b96acc7898afe359b	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-1900000000-277cc1263a84bd8fb441	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-055r-9800000000-5797bbfc4bc8a0229eed	JSpectraViewer
MS	Mass Spectrum (Electron Ionization)	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer

References

References:

Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	27541
HMDB ID	Not Available
Pubchem Compound ID	19069
Kegg ID	C00943
ChemSpider ID	18004
FOODB ID	Not Available
Wikipedia ID	Not Available
BioCyc ID	Not Available

Enzymes

Protein Details

1. 3',5'-cyclic-nucleotide phosphodiesterase 2

General function:: Involved in catalytic activity
Specific function:: Controls the level of cAMP in yeast cells, together with the low-affinity cAMP phosphodiesterase (PDE1)
Gene Name:: PDE2
Uniprot ID:: P06776
Molecular weight:: 60999.19922

Reactions

Adenosine 3',5'-cyclic phosphate + H(2)O → adenosine 5'-phosphate.

Structure for #<Compound:0xa9be8648>

Enzymes

Reactions