NP-MRD: Showing NP-Card for 3deoxyadenosine (NP0293577)

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Record Information

Version

2.0

Created at

2022-09-10 01:39:23 UTC

Updated at

2022-09-10 01:39:24 UTC

NP-MRD ID

NP0293577

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3deoxyadenosine

Description

2-(6-Amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolan-3-ol belongs to the class of organic compounds known as purine 3'-deoxyribonucleosides. Purine 3'-deoxyribonucleosides are compounds consisting of a purine linked to a ribose which lacks a hydroxyl group at position 3. 3deoxyadenosine is found in Ophiocordyceps sinensis. 2-(6-Amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolan-3-ol is a strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 31 33  0  0  0  0  0  0  0  0999 V2000
   -5.0361   -0.1962    1.0009 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9701    0.5389    0.4342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1574    1.8210    0.0339 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1403    2.5180   -0.5052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9052    1.9964   -0.6753 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6686    0.7345   -0.2963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7068    0.0176    0.2559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1895   -1.1966    0.5374 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9065   -1.2088    0.1732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5468   -0.0070   -0.3559 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7335    0.3953   -0.8662 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5665    0.9117    0.1287 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1960   -0.1857    0.7079 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4564    0.1865    1.4300 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4027    0.7744    0.6057 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5263   -1.1015   -0.4351 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5016   -0.7381   -1.4890 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7041   -1.8063   -1.8207 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3809   -1.0494    0.5320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4631    0.1285    1.8842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2687    3.5551   -0.8358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2621   -2.0664    0.2919 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6243    1.1862   -1.6372 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5083   -0.6422    1.4455 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2885    0.8459    2.2945 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9050   -0.7493    1.8213 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1145    1.1377    1.2234 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5653   -0.8950   -0.7955 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3756   -2.1412   -0.1252 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0669   -0.4095   -2.4092 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0664   -2.3544   -2.5540 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
 10  6  1  0
  6  5  2  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  6  7  1  0
 17 11  1  0
  1 19  1  0
  1 20  1  0
  9 22  1  0
 11 23  1  6
 13 24  1  1
 14 25  1  0
 14 26  1  0
 15 27  1  0
 16 28  1  0
 16 29  1  0
 17 30  1  6
 18 31  1  0
  4 21  1  0
M  END


  Mrv1533004241515212D          

 18 20  0  0  0  0            999 V2000
    3.2789    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0098   -1.7070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249   -2.3744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -3.1591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5868   -3.3306    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7403   -2.1195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7403   -1.2945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0728   -0.8096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  2  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  6 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  0  0  0  0
 11 17  1  0  0  0  0
 17 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0293577

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC1=C2N=CN(C3OC(CO)CC3O)C2=NC=N1

> <INCHI_IDENTIFIER>
InChI=1S/C10H13N5O3/c11-8-7-9(13-3-12-8)15(4-14-7)10-6(17)1-5(2-16)18-10/h3-6,10,16-17H,1-2H2,(H2,11,12,13)

> <INCHI_KEY>
OFEZSBMBBKLLBJ-UHFFFAOYSA-N

> <FORMULA>
C10H13N5O3

> <MOLECULAR_WEIGHT>
251.246

> <EXACT_MASS>
251.101839299

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
24.226460305103863

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolan-3-ol

> <ALOGPS_LOGP>
-0.85

> <JCHEM_LOGP>
-1.4006691906666668

> <ALOGPS_LOGS>
-1.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.706912091159193

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.527495093967161

> <JCHEM_PKA_STRONGEST_BASIC>
4.98884814804849

> <JCHEM_POLAR_SURFACE_AREA>
119.31000000000002

> <JCHEM_REFRACTIVITY>
62.09850000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.13e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3deoxyadenosine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  N   UNK     0       6.121   3.850   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       7.454   1.540   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       6.121  -0.770   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       3.322   2.016   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       3.322  -0.476   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       2.846  -1.941   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.752  -3.186   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.846  -4.432   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.322  -5.897   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.829  -6.217   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.382  -3.956   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.382  -2.416   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.136  -1.511   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   10                                                  
CONECT    7    6    2    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    6   11                                                  
CONECT   11   10   12   17                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   13   17                                                       
CONECT   17   16   11   18                                                  
CONECT   18   17                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₀H₁₃N₅O₃

Average Mass

251.2460 Da

Monoisotopic Mass

251.10184 Da

IUPAC Name

2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolan-3-ol

Traditional Name

3deoxyadenosine

CAS Registry Number

Not Available

SMILES

NC1=C2N=CN(C3OC(CO)CC3O)C2=NC=N1

InChI Identifier

InChI=1S/C10H13N5O3/c11-8-7-9(13-3-12-8)15(4-14-7)10-6(17)1-5(2-16)18-10/h3-6,10,16-17H,1-2H2,(H2,11,12,13)

InChI Key

OFEZSBMBBKLLBJ-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
Ophiocordyceps sinensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as purine 3'-deoxyribonucleosides. Purine 3'-deoxyribonucleosides are compounds consisting of a purine linked to a ribose which lacks a hydroxyl group at position 3.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleosides

Sub Class

Purine 3'-deoxyribonucleosides

Direct Parent

Purine 3'-deoxyribonucleosides

Alternative Parents

Substituents

Purine 3'-deoxyribonucleoside
6-aminopurine
Imidazopyrimidine
Purine
Aminopyrimidine
N-substituted imidazole
Pyrimidine
Imidolactam
Azole
Imidazole
Heteroaromatic compound
Tetrahydrofuran
Secondary alcohol
Oxacycle
Azacycle
Organoheterocyclic compound
Amine
Primary amine
Primary alcohol
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Alcohol
Organic nitrogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

a small molecule (CPD-10129 )

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	-0.85	ALOGPS
logP	-1.4	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	13.53	ChemAxon
pKa (Strongest Basic)	4.99	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	119.31 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	62.1 m³·mol⁻¹	ChemAxon
Polarizability	24.23 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

Not Available

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

248010

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3deoxyadenosine (NP0293577)

MOL for NP0293577 (3deoxyadenosine)

3D MOL for NP0293577 (3deoxyadenosine)

3D SDF for NP0293577 (3deoxyadenosine)

3D-SDF for NP0293577 (3deoxyadenosine)

PDB for NP0293577 (3deoxyadenosine)

3D PDB for NP0293577 (3deoxyadenosine)

SMILES for NP0293577 (3deoxyadenosine)

INCHI for NP0293577 (3deoxyadenosine)

Structure for NP0293577 (3deoxyadenosine)

3D Structure for NP0293577 (3deoxyadenosine)