MiMeDB: Showing metabocard for 3',5'-cyclic IMP (MMDBc0032986)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:30:01 UTC

Update Date

2022-08-31 21:54:55 UTC

Metabolite ID

MMDBc0032986

Metabolite Identification

Common Name

3',5'-cyclic IMP

Description

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241222192D          

 22 25  0  0  1  0            999 V2000
   -0.7145    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7540   -1.4521    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2691   -2.1195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7540   -2.7869    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5387   -2.5320    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5387   -1.7070    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2061   -1.2221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1517   -3.0840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5825   -3.5939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1956   -4.1459    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7872   -4.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9802   -3.8910    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    3.2352   -4.6756    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4991   -0.6674    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9840    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4991    0.6674    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3 21  1  0  0  0  0
  3  4  1  0  0  0  0
  4 19  1  0  0  0  0
  5  1  1  0  0  0  0
  3  5  2  0  0  0  0
 22  5  1  0  0  0  0
  6  2  1  0  0  0  0
  4  6  2  0  0  0  0
  7 19  1  1  0  0  0
  8  7  1  0  0  0  0
  7 11  1  0  0  0  0
  9  8  1  0  0  0  0
  9 14  1  1  0  0  0
  9 10  1  0  0  0  0
 10 13  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 13 17  1  0  0  0  0
 15 14  1  0  0  0  0
 17 15  1  0  0  0  0
 17 16  2  0  0  0  0
 17 18  1  0  0  0  0
 20 19  1  0  0  0  0
 21 20  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0032986

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
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

> <INCHI_KEY>
DMJWGQPYNRPLGA-KQYNXXCUSA-N

> <FORMULA>
C10H11N4O7P

> <MOLECULAR_WEIGHT>
330.1907

> <EXACT_MASS>
330.036535238

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
27.77697802621541

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(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

> <ALOGPS_LOGP>
-2.10

> <JCHEM_LOGP>
-2.3666930327815794

> <ALOGPS_LOGS>
-1.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.167559961669655

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8400395194078114

> <JCHEM_PKA_STRONGEST_BASIC>
0.056251351026369356

> <JCHEM_POLAR_SURFACE_AREA>
149.04999999999998

> <JCHEM_REFRACTIVITY>
67.57

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.12e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cyclic imp

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  N   UNK     0      -1.334   0.770   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       0.000  -1.540   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       3.274  -2.711   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.369  -3.956   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       3.274  -5.202   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.739  -4.726   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.739  -3.186   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.985  -2.281   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       5.883  -5.757   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.954  -6.709   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.098  -7.739   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       7.069  -7.583   0.000  0.00  0.00           O+0
HETATM   17  P   UNK     0       5.563  -7.263   0.000  0.00  0.00           P+0
HETATM   18  O   UNK     0       6.039  -8.728   0.000  0.00  0.00           O+0
HETATM   19  N   UNK     0       2.798  -1.246   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       3.703   0.000   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       2.798   1.246   0.000  0.00  0.00           N+0
HETATM   22  O   UNK     0       0.000   3.080   0.000  0.00  0.00           O+0
CONECT    1    2    5                                                       
CONECT    2    1    6                                                       
CONECT    3   21    4    5                                                  
CONECT    4    3   19    6                                                  
CONECT    5    1    3   22                                                  
CONECT    6    2    4                                                       
CONECT    7   19    8   11                                                  
CONECT    8    7    9                                                       
CONECT    9    8   14   10                                                  
CONECT   10    9   13   11                                                  
CONECT   11    7   10   12                                                  
CONECT   12   11                                                            
CONECT   13   10   17                                                       
CONECT   14    9   15                                                       
CONECT   15   14   17                                                       
CONECT   16   17                                                            
CONECT   17   13   15   16   18                                             
CONECT   18   17                                                            
CONECT   19    4    7   20                                                  
CONECT   20   19   21                                                       
CONECT   21    3   20                                                       
CONECT   22    5                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

Synonyms

Value	Source
Cyclic imp	ChEBI
Inosine 3',5'-cyclic monophosphate	ChEBI
Inosine cyclic 3',5'-(hydrogen phosphate)	ChEBI
Inosine 3',5'-cyclic monophosphoric acid	Generator
Inosine cyclic 3',5'-(hydrogen phosphoric acid)	Generator

Molecular Formula

C₁₀H₁₁N₄O₇P

Average Mass

330.1907

Monoisotopic Mass

330.036535238

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 Name

cyclic imp

CAS Registry Number

3545-76-4

SMILES

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

InChI Identifier

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

InChI Key

DMJWGQPYNRPLGA-KQYNXXCUSA-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.

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 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0905000000-9909d05a8bea0ddc163e	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0900000000-8b8b01340e24edbf66b7	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01p9-0900000000-2aaf783de273a2200c1e	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004r-1709000000-e75b96acc7898afe359b	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-1900000000-277cc1263a84bd8fb441	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-055r-9800000000-5797bbfc4bc8a0229eed	2016-09-12	View Spectrum
MS	Mass Spectrum (Electron Ionization)	Not Available	2022-08-06	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-23	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown
Bacteria	Spirochaetes	1

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C00943

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

19069

PDB ID

Not Available

ChEBI ID

27541

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for 3',5'-cyclic IMP (MMDBc0032986)

MOL for #<Metabolite:0x00007fece0699860>

3D MOL for #<Metabolite:0x00007fece0699860>

3D SDF for #<Metabolite:0x00007fece0699860>

3D-SDF for #<Metabolite:0x00007fece0699860>

PDB for #<Metabolite:0x00007fece0699860>

3D PDB for #<Metabolite:0x00007fece0699860>

SMILES for #<Metabolite:0x00007fece0699860>

INCHI for #<Metabolite:0x00007fece0699860>

Structure for #<Metabolite:0x00007fece0699860>

3D Structure for #<Metabolite:0x00007fece0699860>