MiMeDB: Showing metabocard for Adenosine 2'-phosphate (MMDBc0033034)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:31:57 UTC

Update Date

2024-04-30 19:58:54 UTC

Metabolite ID

MMDBc0033034

Metabolite Identification

Common Name

Adenosine 2'-phosphate

Description

Adenosine 2'-phosphate is converted enzymatically from adenosine 2',3'-cyclic phosphate via the enzyme 2',3'-cyclic-nucleotide 3'-phosphodiesterase (EC 3.1.4.37). In the brain, this enzyme acts on 2',3'-cyclic AMP more rapidly than on the UMP or CMP derivatives. In the liver, this enzyme acts on 2',3'-cyclic CMP more rapidly than on the purine derivatives; it also hydrolyses the corresponding 3',5'-cyclic phosphates, more slowly. This latter enzyme has been called cyclic-CMP phosphodiesterase. (KEGG). This enzyme belongs to the family of hydrolases, specifically those acting on phosphoric diester bonds. The systematic name of this enzyme class is nucleoside-2',3'-cyclic-phosphate 2'-nucleotidohydrolase. (Wikipedia).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241222252D          

 23 25  0  0  1  0            999 V2000
    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 N   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
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7540   -1.4521    0.0000 C   0  0  1  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
    2.5387   -1.7070    0.0000 C   0  0  1  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
    1.9840    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5387   -2.5320    0.0000 C   0  0  1  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
    1.4991    0.6674    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2061   -3.0169    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4991   -3.5716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6921   -3.7431    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 N   0  0  0  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
    3.9206   -2.4596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6350   -1.2221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9206   -1.6346    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    3.9206   -0.8096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  8  1  1  0  0  0  0
  1  2  2  0  0  0  0
  2 14  1  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4 18  1  0  0  0  0
  3  5  2  0  0  0  0
  5  6  1  0  0  0  0
  4  6  2  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  7 10  1  0  0  0  0
  8 11  1  0  0  0  0
  9 12  1  0  0  0  0
  9 19  1  6  0  0  0
 10 13  1  0  0  0  0
 11 14  2  0  0  0  0
 12 15  1  6  0  0  0
 12 13  1  0  0  0  0
 13 16  1  1  0  0  0
 16 17  1  0  0  0  0
 19 22  1  0  0  0  0
 22 20  2  0  0  0  0
 22 21  1  0  0  0  0
 22 23  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0033034

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H14N5O7P/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(22-23(18,19)20)6(17)4(1-16)21-10/h2-4,6-7,10,16-17H,1H2,(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1

> <INCHI_KEY>
QDFHPFSBQFLLSW-KQYNXXCUSA-N

> <FORMULA>
C10H14N5O7P

> <MOLECULAR_WEIGHT>
347.2212

> <EXACT_MASS>
347.063084339

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_AVERAGE_POLARIZABILITY>
29.583709389509554

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[(2R,3R,4R,5R)-2-(6-amino-9H-purin-9-yl)-4-hydroxy-5-(hydroxymethyl)oxolan-3-yl]oxy}phosphonic acid

> <ALOGPS_LOGP>
-3.13

> <JCHEM_LOGP>
-4.813372996938782

> <ALOGPS_LOGS>
-2.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.815683881751798

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.6902710437260553

> <JCHEM_PKA_STRONGEST_BASIC>
4.913987171046688

> <JCHEM_POLAR_SURFACE_AREA>
186.06999999999996

> <JCHEM_REFRACTIVITY>
74.06850000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.51e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
adenosine 2'-phosphate

> <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       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       0.000  -1.540   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      -1.334   0.770   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  N   UNK     0       2.798  -1.246   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       4.739  -3.186   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.369  -3.956   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       3.703   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.739  -4.726   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.274  -5.202   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       2.798   1.246   0.000  0.00  0.00           N+0
HETATM   15  O   UNK     0       5.985  -5.632   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.798  -6.667   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.292  -6.987   0.000  0.00  0.00           O+0
HETATM   18  N   UNK     0       0.000   3.080   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0       5.985  -2.281   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       7.318  -4.591   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       8.652  -2.281   0.000  0.00  0.00           O+0
HETATM   22  P   UNK     0       7.318  -3.051   0.000  0.00  0.00           P+0
HETATM   23  O   UNK     0       7.318  -1.511   0.000  0.00  0.00           O+0
CONECT    1    8    2    3                                                  
CONECT    2    1   14    4                                                  
CONECT    3    1    5                                                       
CONECT    4    2   18    6                                                  
CONECT    5    3    6                                                       
CONECT    6    5    4                                                       
CONECT    7    8    9   10                                                  
CONECT    8    1    7   11                                                  
CONECT    9    7   12   19                                                  
CONECT   10    7   13                                                       
CONECT   11    8   14                                                       
CONECT   12    9   15   13                                                  
CONECT   13   10   12   16                                                  
CONECT   14    2   11                                                       
CONECT   15   12                                                            
CONECT   16   13   17                                                       
CONECT   17   16                                                            
CONECT   18    4                                                            
CONECT   19    9   22                                                       
CONECT   20   22                                                            
CONECT   21   22                                                            
CONECT   22   19   20   21   23                                             
CONECT   23   22                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

Synonyms

Value	Source
2'-Adenylic acid	ChEBI
Adenosine 2'-monophosphate	ChEBI
ADENOSINE-2'-monophosphATE	ChEBI
AMP 2'-Phosphate	Kegg
2'-Adenylate	Generator
Adenosine 2'-monophosphoric acid	Generator
ADENOSINE-2'-monophosphoric acid	Generator
AMP 2'-Phosphoric acid	Generator
Adenosine 2'-phosphoric acid	Generator
Adenylic acid	MeSH
Dipotassium, adenosine phosphate	MeSH
2'-AMP	MeSH
2'-Adenosine monophosphate	MeSH
Adenosine 5' phosphate	MeSH
Disodium, adenosine phosphate	MeSH
2' Adenosine monophosphate	MeSH
Adenosine 2' phosphate	MeSH
monoPhosphate, 2'-adenosine	MeSH
Acid, 5'-adenylic	MeSH
Phosphate dipotassium, adenosine	MeSH
AMP	MeSH
Acid, 2'-adenylic	MeSH
Adenosine monophosphate	MeSH
Adenosine 3'-phosphate	MeSH
Adenosine phosphate disodium	MeSH
5'-Phosphate, adenosine	MeSH
Adenosine 5'-phosphate	MeSH
Adenosine phosphate dipotassium	MeSH
Phosphate disodium, adenosine	MeSH
5' Adenylic acid	MeSH
2' Adenylic acid	MeSH
Phosphaden	MeSH
Adenosine 3' phosphate	MeSH
5'-Adenylic acid	MeSH

Molecular Formula

C₁₀H₁₄N₅O₇P

Average Mass

347.2212

Monoisotopic Mass

347.063084339

IUPAC Name

{[(2R,3R,4R,5R)-2-(6-amino-9H-purin-9-yl)-4-hydroxy-5-(hydroxymethyl)oxolan-3-yl]oxy}phosphonic acid

Traditional Name

adenosine 2'-phosphate

CAS Registry Number

130-49-4

SMILES

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

InChI Identifier

InChI=1S/C10H14N5O7P/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(22-23(18,19)20)6(17)4(1-16)21-10/h2-4,6-7,10,16-17H,1H2,(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1

InChI Key

QDFHPFSBQFLLSW-KQYNXXCUSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Pentose phosphates

Alternative Parents

Substituents

Pentose phosphate
N-glycosyl compound
Glycosyl compound
6-aminopurine
Purine
Imidazopyrimidine
Monoalkyl phosphate
Aminopyrimidine
Phosphoric acid ester
Imidolactam
Alkyl phosphate
Pyrimidine
N-substituted imidazole
Organic phosphoric acid derivative
Imidazole
Tetrahydrofuran
Azole
Heteroaromatic compound
Secondary alcohol
Oxacycle
Azacycle
Organoheterocyclic compound
Amine
Alcohol
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Primary amine
Primary alcohol
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

purine ribonucleoside 2'-monophosphate (CHEBI:28223 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	3.51 g/L	ALOGPS
logP	-3.1	ALOGPS
logP	-4.8	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	0.69	ChemAxon
pKa (Strongest Basic)	4.91	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	186.07 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	74.07 m³·mol⁻¹	ChemAxon
Polarizability	29.58 Å³	ChemAxon
Number of Rings	3	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_3_6) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0942000000-5c237eed85b2a16f9799	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0900000000-91830941d3c4df3f32a3	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-1900000000-34129684d1ee8b1b1a37	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0032-5519000000-4032dc31817ae54a7a71	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-3900000000-13da8c715bedb0a7e501	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9400000000-edbf8ea8023cf964ef93	2016-09-12	View Spectrum
MS	Mass Spectrum (Electron Ionization)	Not Available	2022-08-06	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, experimental)		2016-09-19	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50.18 MHz, D₂O, experimental)		2016-09-19	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

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

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	Actinobacteria	1	Human

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 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

C00946

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

94136

PDB ID

Not Available

ChEBI ID

28223

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

HOLLANDER VP, HOLLANDER N, BROWN JD: Inhibition of steroid-mediated pyridine nucleotide transhydrogenase and 17-betta-hydroxysteroid dehydrogenase by 2'adenylic acid. Proc Soc Exp Biol Med. 1959 Jul;101(3):475-7. doi: 10.3181/00379727-101-24986. [PubMed:13675287 ]
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 Adenosine 2'-phosphate (MMDBc0033034)

MOL for #<Metabolite:0x00007fed0805e4f0>

3D MOL for #<Metabolite:0x00007fed0805e4f0>

3D SDF for #<Metabolite:0x00007fed0805e4f0>

3D-SDF for #<Metabolite:0x00007fed0805e4f0>

PDB for #<Metabolite:0x00007fed0805e4f0>

3D PDB for #<Metabolite:0x00007fed0805e4f0>

SMILES for #<Metabolite:0x00007fed0805e4f0>

INCHI for #<Metabolite:0x00007fed0805e4f0>

Structure for #<Metabolite:0x00007fed0805e4f0>

3D Structure for #<Metabolite:0x00007fed0805e4f0>