MiMeDB: Showing metabocard for 2',3'-cyclic AMP (MMDBc0033035)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:31:59 UTC

Update Date

2024-04-30 19:58:59 UTC

Metabolite ID

MMDBc0033035

Metabolite Identification

Common Name

2',3'-cyclic AMP

Description

Adenosine 2',3'-cyclic phosphate is part of the purine metabolism pathway. In this pathway, 2',3'-cyclic AMP is reversibly converted to 3'-AMP via the enzyme 2',3'-cyclic-nucleotide 2'-phosphodiesterase (EC 3.1.4.16). (KEGG).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241222252D          

 22 25  0  0  1  0            999 V2000
   -0.7846    0.6674    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2695    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7846    0.6674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7846   -0.6674    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7846   -0.6674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695    0.0000    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0396    1.4521    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8242    1.7070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5546    2.1195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8242    2.5320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5387    1.2945    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0396    2.7869    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9840    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9840   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5387    2.9445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2531    1.7070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2531    2.5320    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5387    3.7695    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0396   -1.4521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4875   -2.0652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  1  1  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  6  0  0  0
  4  6  1  0  0  0  0
  2  6  1  0  0  0  0
  6 21  1  1  0  0  0
  4  7  1  6  0  0  0
  5  8  1  0  0  0  0
  7  8  1  0  0  0  0
  8 15  1  0  0  0  0
  8 16  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  2  0  0  0  0
 10 13  1  0  0  0  0
 11 14  2  0  0  0  0
 12 17  1  0  0  0  0
 12 14  1  0  0  0  0
 13 18  2  0  0  0  0
 17 19  2  0  0  0  0
 17 20  1  0  0  0  0
 18 19  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0033035

> <DATABASE_NAME>
MIME

> <SMILES>
NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@H]2OP(O)(=O)O[C@@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C10H12N5O6P/c11-8-5-9(13-2-12-8)15(3-14-5)10-7-6(4(1-16)19-10)20-22(17,18)21-7/h2-4,6-7,10,16H,1H2,(H,17,18)(H2,11,12,13)/t4-,6-,7-,10-/m1/s1

> <INCHI_KEY>
KMYWVDDIPVNLME-KQYNXXCUSA-N

> <FORMULA>
C10H12N5O6P

> <MOLECULAR_WEIGHT>
329.2059

> <EXACT_MASS>
329.052519653

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
28.282347602081263

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3aR,4R,6R,6aR)-4-(6-amino-9H-purin-9-yl)-2-hydroxy-6-(hydroxymethyl)-tetrahydro-2H-2λ⁵-furo[3,4-d][1,3,2]dioxaphosphol-2-one

> <ALOGPS_LOGP>
-2.51

> <JCHEM_LOGP>
-3.8298289107849044

> <ALOGPS_LOGS>
-1.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.584307323434835

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7592537911346091

> <JCHEM_PKA_STRONGEST_BASIC>
4.9887015214332004

> <JCHEM_POLAR_SURFACE_AREA>
154.84

> <JCHEM_REFRACTIVITY>
70.28949999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.59e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2',3'-cyclic amp

> <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  C   UNK     0      -1.465   1.246   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.370   0.000   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.000   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -0.770   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.465   1.246   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -1.465  -1.246   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.465  -1.246   0.000  0.00  0.00           O+0
HETATM    8  P   UNK     0       2.370   0.000   0.000  0.00  0.00           P+0
HETATM    9  N   UNK     0      -1.941   2.711   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      -3.405   3.186   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.035   3.956   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.405   4.726   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      -4.739   2.416   0.000  0.00  0.00           N+0
HETATM   14  N   UNK     0      -1.941   5.202   0.000  0.00  0.00           N+0
HETATM   15  O   UNK     0       3.703   0.770   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       3.703  -0.770   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -4.739   5.496   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -6.072   3.186   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0      -6.072   4.726   0.000  0.00  0.00           N+0
HETATM   20  N   UNK     0      -4.739   7.036   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0      -1.941  -2.711   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -0.910  -3.855   0.000  0.00  0.00           O+0
CONECT    1    9    2    3                                                  
CONECT    2    1    6                                                       
CONECT    3    1    4    5                                                  
CONECT    4    3    6    7                                                  
CONECT    5    3    8                                                       
CONECT    6    4    2   21                                                  
CONECT    7    4    8                                                       
CONECT    8    5    7   15   16                                             
CONECT    9    1   10   11                                                  
CONECT   10    9   12   13                                                  
CONECT   11    9   14                                                       
CONECT   12   10   17   14                                                  
CONECT   13   10   18                                                       
CONECT   14   11   12                                                       
CONECT   15    8                                                            
CONECT   16    8                                                            
CONECT   17   12   19   20                                                  
CONECT   18   13   19                                                       
CONECT   19   17   18                                                       
CONECT   20   17                                                            
CONECT   21    6   22                                                       
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

Synonyms

Value	Source
(3AR,4R,6R,6ar)-4-(6-amino-9H-purin-9-yl)-6-(hydroxymethyl)tetrahydrofuro[3,4-D][1,3,2]dioxaphosphol-2-ol 2-oxide	ChEBI
Adenosine cyclic 2',3'-(hydrogen phosphate)	ChEBI
Adenosine cyclic 2',3'-(hydrogen phosphoric acid)	Generator
2',3'-Cyclic AMP, monosodium salt	MeSH
Adenosine cyclic 2,3 monophosphate	MeSH
Adenosine cyclic-2',3'-monophosphate	MeSH
Adenosine cyclic 2',3'-monophosphate	MeSH
2',3'-Cyclic AMP, sodium salt	MeSH

Molecular Formula

C₁₀H₁₂N₅O₆P

Average Mass

329.2059

Monoisotopic Mass

329.052519653

IUPAC Name

(3aR,4R,6R,6aR)-4-(6-amino-9H-purin-9-yl)-2-hydroxy-6-(hydroxymethyl)-tetrahydro-2H-2λ⁵-furo[3,4-d][1,3,2]dioxaphosphol-2-one

Traditional Name

2',3'-cyclic amp

CAS Registry Number

634-01-5

SMILES

NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@H]2OP(O)(=O)O[C@@H]12

InChI Identifier

InChI=1S/C10H12N5O6P/c11-8-5-9(13-2-12-8)15(3-14-5)10-7-6(4(1-16)19-10)20-22(17,18)21-7/h2-4,6-7,10,16H,1H2,(H,17,18)(H2,11,12,13)/t4-,6-,7-,10-/m1/s1

InChI Key

KMYWVDDIPVNLME-KQYNXXCUSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2',3'-cyclic purine nucleotides. These are purine nucleotides in which the oxygen atoms linked to the C2 and C3 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

2',3'-cyclic purine nucleotides

Alternative Parents

Substituents

2',3'-cyclic purine ribonucleotide
Ribonucleoside 3'-phosphate
6-aminopurine
Imidazopyrimidine
Purine
Aminopyrimidine
Monosaccharide
Imidolactam
Pyrimidine
N-substituted imidazole
Organic phosphoric acid derivative
Azole
1,3_dioxaphospholane
Heteroaromatic compound
Imidazole
Tetrahydrofuran
Oxacycle
Azacycle
Organoheterocyclic compound
Primary amine
Alcohol
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Amine
Primary alcohol
Organonitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

2',3'-cyclic purine nucleotide (CHEBI:27844 )
2',3'-Cyclic nucleotides (C02353 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	3.59 g/L	ALOGPS
logP	-2.5	ALOGPS
logP	-3.8	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	1.76	ChemAxon
pKa (Strongest Basic)	4.99	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	154.84 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	70.29 m³·mol⁻¹	ChemAxon
Polarizability	28.28 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_3) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-1904000000-bfe4e467d8cc3a6ac36e	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0900000000-8c5058701da423b1d797	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052r-3900000000-7b5d0ee59f4dd0cffb13	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0059-0509000000-f71234416c075a292539	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0900000000-43e46da0ce61f1a335ae	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-053r-4900000000-bd9f1b32b356608b74fc	2016-09-12	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Placenta

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

Not Available

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

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
Human Blood	Detected and Quantified	0.026	0.00096			uM	Adult (>18 years old)	Both	Normal	HMDB	8186443
Human Placenta	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597

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

C02353

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101812

PDB ID

Not Available

ChEBI ID

27844

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Krall JF, Swensen JL, Korenman SG: Hormonal control of uterine contraction. Characterization od cyclic AMP-dependent membrane properties in the myometrium. Biochim Biophys Acta. 1976 Nov 2;448(4):578-88. doi: 10.1016/0005-2736(76)90111-5. [PubMed:184841 ]
Schoffstall AM: Prebiotic phosphorylation of nucleosides in formamide. Orig Life. 1976 Dec;7(4):399-412. doi: 10.1007/BF00927935. [PubMed:1023139 ]
Ghandour MS, Derer P, Labourdette G, Delaunoy JP, Langley OK: Glial cell markers in the reeler mutant mouse: a biochemical and immunohistological study. J Neurochem. 1981 Jan;36(1):195-200. doi: 10.1111/j.1471-4159.1981.tb02395.x. [PubMed:6257845 ]
Wells MR, Sprinkle TJ: Purification of rat 2',3'-cyclic nucleotide 3'-phosphodiesterase. J Neurochem. 1981 Feb;36(2):633-9. doi: 10.1111/j.1471-4159.1981.tb01636.x. [PubMed:6257858 ]
Reddy NB, Askanas V, Engel WK: Demonstration of 2',3'-cyclic nucleotide 3'-phosphohydrolase in cultured human Schwann cells. J Neurochem. 1982 Sep;39(3):887-9. doi: 10.1111/j.1471-4159.1982.tb07977.x. [PubMed:6284879 ]
Cheng C, Fan C, Wan R, Tong C, Miao Z, Chen J, Zhao Y: Phosphorylation of adenosine with trimetaphosphate under simulated prebiotic conditions. Orig Life Evol Biosph. 2002 Jun;32(3):219-24. doi: 10.1023/a:1016513114799. [PubMed:12227426 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Showing metabocard for 2',3'-cyclic AMP (MMDBc0033035)

MOL for #<Metabolite:0x00007fecf0c3ae08>

3D MOL for #<Metabolite:0x00007fecf0c3ae08>

3D SDF for #<Metabolite:0x00007fecf0c3ae08>

3D-SDF for #<Metabolite:0x00007fecf0c3ae08>

PDB for #<Metabolite:0x00007fecf0c3ae08>

3D PDB for #<Metabolite:0x00007fecf0c3ae08>

SMILES for #<Metabolite:0x00007fecf0c3ae08>

INCHI for #<Metabolite:0x00007fecf0c3ae08>

Structure for #<Metabolite:0x00007fecf0c3ae08>

3D Structure for #<Metabolite:0x00007fecf0c3ae08>