NP-MRD: Showing NP-Card for 3'-adenylic acid (NP0260394)

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Record Information

Version

2.0

Created at

2022-09-08 02:33:06 UTC

Updated at

2022-09-08 02:33:06 UTC

NP-MRD ID

NP0260394

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3'-adenylic acid

Description

Adenosine-3-phosphoric acid belongs to the class of organic compounds known as ribonucleoside 3'-phosphates. These are ribonucleosides that contain a phosphate group attached to the C-3 carbon of the ribose or deoxyribose moiety. The nucleobases here are limited to purine, pyrimidine, and pyridine derivatives. 3'-adenylic acid is found in Helianthus tuberosus and Notechis scutatus. Adenosine-3-phosphoric acid is a strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 39  0  0  0  0  0  0  0  0999 V2000
    6.0396    0.1833    0.5303 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7719    0.3933   -0.0610 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5911    1.0718   -1.2177 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3678    1.2502   -1.7482 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3206    0.7372   -1.1014 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3918    0.0504    0.0481 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6646   -0.1250    0.5831 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4629   -0.8288    1.7082 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1707   -1.0690    1.8569 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4691   -0.5227    0.8185 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0685   -0.5951    0.6692 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3707   -1.2767   -0.4613 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7190   -1.0380   -0.5449 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4357   -2.2452    0.0724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0759   -3.3712   -0.6578 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0386    0.2121    0.2200 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7919    1.1190   -0.4785 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1342    1.5211    0.4692 P   0  0  0  0  0  5  0  0  0  0  0  0
   -5.0032    0.3066    0.7414 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0948    2.6963   -0.2637 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6415    2.0933    2.0041 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6196    0.7409    0.4913 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2476    1.3743   -0.6938 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7313   -0.4013    0.0305 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3033    0.5917    1.4443 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3037    1.8065   -2.6805 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7417   -1.6271    2.6973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4187   -1.0816    1.5397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0924   -0.9606   -1.5910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0202   -2.3337    1.1118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5188   -2.1447    0.0449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4468   -3.9440   -0.1367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4834   -0.0349    1.2185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7211    2.2402   -0.8660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4810    3.0724    1.8880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5763    1.3816    1.3658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4671    0.7575   -1.4432 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
 16 17  1  0
 17 18  1  0
 18 20  1  0
 18 21  1  0
 18 19  2  0
 16 22  1  0
 22 23  1  0
 10  6  1  0
  6  5  2  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  6  7  1  0
 22 11  1  0
  1 24  1  0
  1 25  1  0
  9 27  1  0
 11 28  1  1
 13 29  1  6
 14 30  1  0
 14 31  1  0
 15 32  1  0
 16 33  1  1
 20 34  1  0
 21 35  1  0
 22 36  1  1
 23 37  1  0
  4 26  1  0
M  END


  Mrv1652310061708282D          

 23 25  0  0  0  0            999 V2000
   -0.5683   -1.4940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0992   -1.0091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3687   -0.5966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -1.2640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.0709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3220   -1.1584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1937   -0.5966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7527   -2.3917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7742   -3.0271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1172   -1.4132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0992   -0.1841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -2.0486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9457   -2.2201    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  7  4  1  0  0  0  0
  7  6  1  0  0  0  0
  8  5  2  0  0  0  0
  9  5  1  0  0  0  0
 10  6  1  0  0  0  0
 11  8  1  0  0  0  0
 12  2  2  0  0  0  0
 12  8  1  0  0  0  0
 13  2  1  0  0  0  0
 13  9  2  0  0  0  0
 14  3  2  0  0  0  0
 14  5  1  0  0  0  0
 15  3  1  0  0  0  0
 15  9  1  0  0  0  0
 15 10  1  0  0  0  0
 16  1  1  0  0  0  0
 17  6  1  0  0  0  0
 21  4  1  0  0  0  0
 21 10  1  0  0  0  0
 22  7  1  0  0  0  0
 23 18  1  0  0  0  0
 23 19  1  0  0  0  0
 23 20  2  0  0  0  0
 23 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0260394

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC1=C2N=CN(C3OC(CO)C(OP(O)(O)=O)C3O)C2=NC=N1

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

> <INCHI_KEY>
LNQVTSROQXJCDD-UHFFFAOYSA-N

> <FORMULA>
C10H14N5O7P

> <MOLECULAR_WEIGHT>
347.224

> <EXACT_MASS>
347.063084809

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
29.962969965618996

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-3.14

> <JCHEM_LOGP>
-4.869960100943887

> <ALOGPS_LOGS>
-2.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.901547409193856

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.8655335134754503

> <JCHEM_PKA_STRONGEST_BASIC>
3.91708863382946

> <JCHEM_POLAR_SURFACE_AREA>
186.06999999999996

> <JCHEM_REFRACTIVITY>
74.0685

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.48e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3'-adenylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-OCT-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-OCT-17         0                                  
HETATM    1  C   UNK     0      -1.061  -2.789   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.185  -1.884   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.555  -1.114   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.650  -2.359   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.650   0.132   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       4.924   5.923   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0       6.258   3.613   0.000  0.00  0.00           N+0
HETATM   13  N   UNK     0       4.924   1.303   0.000  0.00  0.00           N+0
HETATM   14  N   UNK     0       2.126   4.089   0.000  0.00  0.00           N+0
HETATM   15  N   UNK     0       2.126   1.597   0.000  0.00  0.00           N+0
HETATM   16  O   UNK     0      -2.468  -2.162   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       4.095  -1.114   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       5.138  -4.464   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       3.312  -5.651   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       3.952  -2.638   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       0.185  -0.344   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       2.126  -3.824   0.000  0.00  0.00           O+0
HETATM   23  P   UNK     0       3.632  -4.144   0.000  0.00  0.00           P+0
CONECT    1    4   16                                                       
CONECT    2   12   13                                                       
CONECT    3   14   15                                                       
CONECT    4    1    7   21                                                  
CONECT    5    8    9   14                                                  
CONECT    6    7   10   17                                                  
CONECT    7    4    6   22                                                  
CONECT    8    5   11   12                                                  
CONECT    9    5   13   15                                                  
CONECT   10    6   15   21                                                  
CONECT   11    8                                                            
CONECT   12    2    8                                                       
CONECT   13    2    9                                                       
CONECT   14    3    5                                                       
CONECT   15    3    9   10                                                  
CONECT   16    1                                                            
CONECT   17    6                                                            
CONECT   18   23                                                            
CONECT   19   23                                                            
CONECT   20   23                                                            
CONECT   21    4   10                                                       
CONECT   22    7   23                                                       
CONECT   23   18   19   20   22                                             
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol

Synonyms

Value	Source
Adenosine-3-phosphate	Generator

Chemical Formula

C₁₀H₁₄N₅O₇P

Average Mass

347.2240 Da

Monoisotopic Mass

347.06308 Da

IUPAC Name

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

Traditional Name

3'-adenylic acid

CAS Registry Number

Not Available

SMILES

NC1=C2N=CN(C3OC(CO)C(OP(O)(O)=O)C3O)C2=NC=N1

InChI Identifier

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

InChI Key

LNQVTSROQXJCDD-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Helianthus tuberosus	LOTUS Database	35616633
Notechis scutatus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ribonucleoside 3'-phosphates. These are ribonucleosides that contain a phosphate group attached to the C-3 carbon of the ribose or deoxyribose moiety. The nucleobases here are limited to purine, pyrimidine, and pyridine derivatives.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Ribonucleoside 3'-phosphates

Sub Class

Not Available

Direct Parent

Ribonucleoside 3'-phosphates

Alternative Parents

Substituents

Pentose phosphate
Ribonucleoside 3'-phosphate
Glycosyl compound
N-glycosyl compound
6-aminopurine
Pentose monosaccharide
Monosaccharide phosphate
Purine
Imidazopyrimidine
Aminopyrimidine
Monoalkyl phosphate
Organic phosphoric acid derivative
Phosphoric acid ester
N-substituted imidazole
Monosaccharide
Pyrimidine
Imidolactam
Alkyl phosphate
Heteroaromatic compound
Tetrahydrofuran
Azole
Imidazole
Secondary alcohol
Oxacycle
Azacycle
Organoheterocyclic compound
Primary amine
Amine
Alcohol
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Primary alcohol
Organooxygen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-3.1	ALOGPS
logP	-4.9	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	0.87	ChemAxon
pKa (Strongest Basic)	3.92	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	29.96 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

External Links

HMDB ID

HMDB0155034

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

256105

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3'-adenylic acid (NP0260394)

MOL for NP0260394 (3'-adenylic acid)

3D MOL for NP0260394 (3'-adenylic acid)

3D SDF for NP0260394 (3'-adenylic acid)

3D-SDF for NP0260394 (3'-adenylic acid)

PDB for NP0260394 (3'-adenylic acid)

3D PDB for NP0260394 (3'-adenylic acid)

SMILES for NP0260394 (3'-adenylic acid)

INCHI for NP0260394 (3'-adenylic acid)

Structure for NP0260394 (3'-adenylic acid)

3D Structure for NP0260394 (3'-adenylic acid)