NP-MRD: Showing NP-Card for (2r,3r,4r,5r)-5-(6-aminopurin-9-yl)-2-(1-hydroxyethyl)-4-sulfanyloxolan-3-ol (NP0271709)

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Record Information

Version

2.0

Created at

2022-09-08 18:05:36 UTC

Updated at

2022-09-08 18:05:36 UTC

NP-MRD ID

NP0271709

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3r,4r,5r)-5-(6-aminopurin-9-yl)-2-(1-hydroxyethyl)-4-sulfanyloxolan-3-ol

Description

SCHEMBL101383 belongs to the class of organic compounds known as 6-aminopurines. These are purines that carry an amino group at position 6. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring. (2r,3r,4r,5r)-5-(6-aminopurin-9-yl)-2-(1-hydroxyethyl)-4-sulfanyloxolan-3-ol is found in Glehnia littoralis. Based on a literature review very few articles have been published on SCHEMBL101383.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 35 37  0  0  0  0  0  0  0  0999 V2000
   -2.9584   -0.0344    2.6316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2572   -0.1947    1.1550 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0771   -1.5418    0.8472 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2335    0.6033    0.3652 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9451    0.2473    0.6698 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2221    0.2207   -0.5312 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0214   -0.4433   -0.4153 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3349   -1.7269   -0.6215 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6459   -1.9042   -0.3889 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1982   -0.7216   -0.0258 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4738   -0.3225    0.3211 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5230   -1.2656    0.3382 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6689    0.9821    0.6365 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6584    1.8680    0.6153 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4173    1.4799    0.2779 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1753    0.1880   -0.0445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2178   -0.4805   -1.4294 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7716   -0.5222   -3.1354 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4327    0.3790   -1.1197 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3102    1.6080   -1.7471 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2477    0.8245    2.7751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8954    0.1600    3.2037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5017   -0.9293    3.0761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2599    0.1804    0.8771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8254   -1.9103    0.3052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3540    1.6877    0.6346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1244    1.2816   -0.8476 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5866   -2.4611   -0.9305 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3921   -1.0728   -0.1926 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4219   -2.1312    0.8717 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8482    2.9187    0.8761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4201   -1.4871   -0.9765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6471    0.1137   -4.0065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3772   -0.1438   -1.3442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2871    1.5670   -2.7209 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 19  4  1  0
 16  7  1  0
 16 10  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  1
  3 25  1  0
  4 26  1  6
  6 27  1  6
 17 32  1  1
 18 33  1  0
 19 34  1  1
 20 35  1  0
  8 28  1  0
 12 29  1  0
 12 30  1  0
 14 31  1  0
M  END


  Mrv1652309082220052D          

 20 22  0  0  1  0            999 V2000
   -0.4820   -4.5353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5683   -3.7149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3220   -3.3793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0992   -3.2299    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0992   -2.4049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.9521    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 N   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
    2.6378   -1.5229    0.0000 N   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
    1.3687   -2.8174    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1937   -2.8174    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -3.4849    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1387   -4.2695    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
  4  2  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 10 16  1  0  0  0  0
  7 16  1  0  0  0  0
  6 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
  4 19  1  0  0  0  0
 19 20  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0271709

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(O)[C@H]1O[C@H]([C@H](S)[C@@H]1O)N1C=NC2=C(N)N=CN=C12

> <INCHI_IDENTIFIER>
InChI=1S/C11H15N5O3S/c1-4(17)7-6(18)8(20)11(19-7)16-3-15-5-9(12)13-2-14-10(5)16/h2-4,6-8,11,17-18,20H,1H3,(H2,12,13,14)/t4?,6-,7-,8-,11-/m1/s1

> <INCHI_KEY>
VIUIEFBIPFASJW-XDTOVJCPSA-N

> <FORMULA>
C11H15N5O3S

> <MOLECULAR_WEIGHT>
297.33

> <EXACT_MASS>
297.089560537

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
28.956857181449642

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-(1-hydroxyethyl)-4-sulfanyloxolan-3-ol

> <JCHEM_LOGP>
-0.6139301873333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.870476512105263

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.352388670993165

> <JCHEM_PKA_STRONGEST_BASIC>
3.9323767625906694

> <JCHEM_POLAR_SURFACE_AREA>
119.31

> <JCHEM_REFRACTIVITY>
73.6176

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-2-(1-hydroxyethyl)-4-sulfanyloxolan-3-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.900  -8.466   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.061  -6.934   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -2.468  -6.308   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.185  -6.029   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.185  -4.489   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       2.126  -2.549   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       2.126  -0.057   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       4.924   1.777   0.000  0.00  0.00           N+0
HETATM   13  N   UNK     0       6.258  -0.533   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       4.924  -2.843   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.555  -5.259   0.000  0.00  0.00           C+0
HETATM   18  S   UNK     0       4.095  -5.259   0.000  0.00  0.00           S+0
HETATM   19  C   UNK     0       1.650  -6.505   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.126  -7.970   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   19                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   17                                                  
CONECT    7    6    8   16                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   16                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   10    7                                                  
CONECT   17    6   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17    4   20                                                  
CONECT   20   19                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₁H₁₅N₅O₃S

Average Mass

297.3300 Da

Monoisotopic Mass

297.08956 Da

IUPAC Name

(2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-(1-hydroxyethyl)-4-sulfanyloxolan-3-ol

Traditional Name

(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-2-(1-hydroxyethyl)-4-sulfanyloxolan-3-ol

CAS Registry Number

Not Available

SMILES

CC(O)[C@H]1O[C@H]([C@H](S)[C@@H]1O)N1C=NC2=C(N)N=CN=C12

InChI Identifier

InChI=1S/C11H15N5O3S/c1-4(17)7-6(18)8(20)11(19-7)16-3-15-5-9(12)13-2-14-10(5)16/h2-4,6-8,11,17-18,20H,1H3,(H2,12,13,14)/t4?,6-,7-,8-,11-/m1/s1

InChI Key

VIUIEFBIPFASJW-XDTOVJCPSA-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
Glehnia littoralis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 6-aminopurines. These are purines that carry an amino group at position 6. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Imidazopyrimidines

Sub Class

Purines and purine derivatives

Direct Parent

6-aminopurines

Alternative Parents

Substituents

6-aminopurine
Aminopyrimidine
Imidolactam
Pyrimidine
N-substituted imidazole
Heteroaromatic compound
Azole
Oxolane
Imidazole
Secondary alcohol
Alkylthiol
Oxacycle
Azacycle
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Organosulfur compound
Primary amine
Hydrocarbon derivative
Amine
Organic oxygen compound
Alcohol
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	-0.61	ChemAxon
pKa (Strongest Acidic)	9.35	ChemAxon
pKa (Strongest Basic)	3.93	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	119.31 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	73.62 m³·mol⁻¹	ChemAxon
Polarizability	28.96 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

24769445

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71431122

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,3r,4r,5r)-5-(6-aminopurin-9-yl)-2-(1-hydroxyethyl)-4-sulfanyloxolan-3-ol (NP0271709)

MOL for NP0271709 ((2r,3r,4r,5r)-5-(6-aminopurin-9-yl)-2-(1-hydroxyethyl)-4-sulfanyloxolan-3-ol)

3D MOL for NP0271709 ((2r,3r,4r,5r)-5-(6-aminopurin-9-yl)-2-(1-hydroxyethyl)-4-sulfanyloxolan-3-ol)

3D SDF for NP0271709 ((2r,3r,4r,5r)-5-(6-aminopurin-9-yl)-2-(1-hydroxyethyl)-4-sulfanyloxolan-3-ol)

3D-SDF for NP0271709 ((2r,3r,4r,5r)-5-(6-aminopurin-9-yl)-2-(1-hydroxyethyl)-4-sulfanyloxolan-3-ol)

PDB for NP0271709 ((2r,3r,4r,5r)-5-(6-aminopurin-9-yl)-2-(1-hydroxyethyl)-4-sulfanyloxolan-3-ol)

3D PDB for NP0271709 ((2r,3r,4r,5r)-5-(6-aminopurin-9-yl)-2-(1-hydroxyethyl)-4-sulfanyloxolan-3-ol)

SMILES for NP0271709 ((2r,3r,4r,5r)-5-(6-aminopurin-9-yl)-2-(1-hydroxyethyl)-4-sulfanyloxolan-3-ol)

INCHI for NP0271709 ((2r,3r,4r,5r)-5-(6-aminopurin-9-yl)-2-(1-hydroxyethyl)-4-sulfanyloxolan-3-ol)

Structure for NP0271709 ((2r,3r,4r,5r)-5-(6-aminopurin-9-yl)-2-(1-hydroxyethyl)-4-sulfanyloxolan-3-ol)

3D Structure for NP0271709 ((2r,3r,4r,5r)-5-(6-aminopurin-9-yl)-2-(1-hydroxyethyl)-4-sulfanyloxolan-3-ol)