NP-MRD: Showing NP-Card for 5'-s-ethyl-5'-thioadenosine (NP0329330)

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Record Information

Version

2.0

Created at

2022-09-12 13:37:18 UTC

Updated at

2022-09-12 13:37:18 UTC

NP-MRD ID

NP0329330

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5'-s-ethyl-5'-thioadenosine

Description

5'-s-ethyl-5'-thioadenosine is found in Trypanosoma brucei.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 40  0  0  0  0  0  0  0  0999 V2000
   -4.2710    1.4548    1.0270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7811    1.3629   -0.4165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1300   -0.2578   -1.0844 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1789   -1.5186   -0.2521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7284   -1.3811   -0.5443 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1642   -0.1645   -0.1544 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1798   -0.3733   -0.5302 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0624    0.5892    0.0434 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8047    1.6271    0.8712 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9515    2.2767    1.1558 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9597    1.6702    0.5189 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3218    1.9088    0.4546 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9302    2.9795    1.1507 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0520    1.0665   -0.3107 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5092    0.0440   -0.9838 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1874   -0.1682   -0.9070 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3883    0.6169   -0.1723 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5158   -1.7604   -0.0477 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0704   -2.4499   -1.1019 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8537   -2.3558    0.2156 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9317   -3.6366   -0.3292 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8796    0.5525    1.2270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3831    1.4060    1.6915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8523    2.3921    1.2061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3047    2.1462   -1.0416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6885    1.5398   -0.4636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4954   -2.5140   -0.6801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4054   -1.6051    0.8324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5555   -1.5781   -1.6299 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1700   -0.3198   -1.6520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2137    1.8494    1.2202 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8710    2.8087    1.5950 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5298    3.9246    1.2634 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0980   -0.6299   -1.5969 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1448   -1.7541    0.8635 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6021   -3.2348   -0.8406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0338   -2.3442    1.2912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4979   -4.1699    0.2844 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 17  2  0
 17 16  1  0
 16 15  2  0
 15 14  1  0
 14 12  2  0
 12 13  1  0
  7 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20  5  1  0
 17  8  1  0
 12 11  1  0
  5 29  1  6
  4 27  1  0
  4 28  1  0
  2 25  1  0
  2 26  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  7 30  1  6
  9 31  1  0
 15 34  1  0
 13 32  1  0
 13 33  1  0
 18 35  1  1
 19 36  1  0
 20 37  1  1
 21 38  1  0
M  END

3DH
  Mrv0541 02241213102D          

 25 27  0  0  0  0            999 V2000
   -1.5966   -3.2393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6829   -2.4188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0154   -1.9339    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1017   -1.1134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4342   -0.6285    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4342    0.1965    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3504   -0.8834    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6053   -1.6681    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8353   -0.2160    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6603   -0.2160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3504    0.4514    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6053    1.2361    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1204    1.9035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6053    2.5709    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3900    2.3160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3900    1.4910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1044    1.0785    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8189    1.4910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8189    2.3160    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1044    2.7285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1044    3.5535    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9545   -0.3634    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0625   -1.2963    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1004   -0.7363    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0625    0.8643    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  5 22  1  6  0  0  0
  6 11  1  0  0  0  0
  7  5  1  0  0  0  0
  7  9  1  0  0  0  0
  7 23  1  1  0  0  0
  7  8  1  6  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
  9 24  1  1  0  0  0
 11 12  1  1  0  0  0
 11 25  1  6  0  0  0
 12 16  1  0  0  0  0
 13 12  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 20  1  0  0  0  0
 16 15  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 20 19  2  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0329330

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]1(CSCC)O[C@@]([H])(N2C=NC3=C2N=CN=C3N)[C@]([H])(O)[C@]1([H])O

> <INCHI_IDENTIFIER>
InChI=1S/C12H17N5O3S/c1-2-21-3-6-8(18)9(19)12(20-6)17-5-16-7-10(13)14-4-15-11(7)17/h4-6,8-9,12,18-19H,2-3H2,1H3,(H2,13,14,15)/t6-,8-,9-,12-/m1/s1

> <INCHI_KEY>
HMXHURAGFHWODC-WOUKDFQISA-N

> <FORMULA>
C12H17N5O3S

> <MOLECULAR_WEIGHT>
311.36

> <EXACT_MASS>
311.105210125

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
31.60185519765141

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3R,4S,5S)-2-(6-amino-9H-purin-9-yl)-5-[(ethylsulfanyl)methyl]oxolane-3,4-diol

> <ALOGPS_LOGP>
0.42

> <JCHEM_LOGP>
-0.3554627353333335

> <ALOGPS_LOGS>
-1.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.012975414117204

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.471827501350823

> <JCHEM_PKA_STRONGEST_BASIC>
4.988448217054972

> <JCHEM_POLAR_SURFACE_AREA>
119.30999999999999

> <JCHEM_REFRACTIVITY>
78.827

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.00e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5'-S-ethyl-5'-thioadenosine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 3DH                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -2.980  -6.047   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.141  -4.515   0.000  0.00  0.00           C+0
HETATM    3  S   UNK     0      -1.895  -3.610   0.000  0.00  0.00           S+0
HETATM    4  C   UNK     0      -2.057  -2.078   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.811  -1.173   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.811   0.367   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.654  -1.649   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.130  -3.114   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.559  -0.403   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       3.099  -0.403   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.654   0.843   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       1.130   2.307   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       0.225   3.553   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       1.130   4.799   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       2.595   4.323   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.595   2.783   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       3.928   2.013   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       5.262   2.783   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       5.262   4.323   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       3.928   5.093   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       3.928   6.633   0.000  0.00  0.00           N+0
HETATM   22  H   UNK     0      -1.782  -0.678   0.000  0.00  0.00           H+0
HETATM   23  H   UNK     0      -0.117  -2.420   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0       2.054  -1.374   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0      -0.117   1.613   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   22    7                                             
CONECT    6    5   11                                                       
CONECT    7    5    9   23    8                                             
CONECT    8    7                                                            
CONECT    9    7   10   11   24                                             
CONECT   10    9                                                            
CONECT   11    6    9   12   25                                             
CONECT   12   11   16   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   20   16                                                  
CONECT   16   12   15   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   15   19   21                                                  
CONECT   21   20                                                            
CONECT   22    5                                                            
CONECT   23    7                                                            
CONECT   24    9                                                            
CONECT   25   11                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

View in JSmol

Synonyms

Value	Source
S-Adenosylethane	ChEBI

Chemical Formula

C₁₂H₁₇N₅O₃S

Average Mass

311.3600 Da

Monoisotopic Mass

311.10521 Da

IUPAC Name

(2R,3R,4S,5S)-2-(6-amino-9H-purin-9-yl)-5-[(ethylsulfanyl)methyl]oxolane-3,4-diol

Traditional Name

5'-S-ethyl-5'-thioadenosine

CAS Registry Number

Not Available

SMILES

[H][C@]1(CSCC)O[C@@]([H])(N2C=NC3=C2N=CN=C3N)[C@]([H])(O)[C@]1([H])O

InChI Identifier

InChI=1S/C12H17N5O3S/c1-2-21-3-6-8(18)9(19)12(20-6)17-5-16-7-10(13)14-4-15-11(7)17/h4-6,8-9,12,18-19H,2-3H2,1H3,(H2,13,14,15)/t6-,8-,9-,12-/m1/s1

InChI Key

HMXHURAGFHWODC-WOUKDFQISA-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
Trypanosoma brucei	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 5'-deoxy-5'-thionucleosides. These are 5'-deoxyribonucleosides in which the ribose is thio-substituted at the 5'position by a S-alkyl group.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

5'-deoxyribonucleosides

Sub Class

5'-deoxy-5'-thionucleosides

Direct Parent

5'-deoxy-5'-thionucleosides

Alternative Parents

Substituents

5'-deoxy-5'-thionucleoside
Glycosyl compound
N-glycosyl compound
6-aminopurine
Pentose monosaccharide
Imidazopyrimidine
Purine
Aminopyrimidine
Monosaccharide
N-substituted imidazole
Pyrimidine
Imidolactam
Azole
Tetrahydrofuran
Imidazole
Heteroaromatic compound
Secondary alcohol
1,2-diol
Organoheterocyclic compound
Dialkylthioether
Sulfenyl compound
Thioether
Azacycle
Oxacycle
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organopnictogen compound
Amine
Primary amine
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Organosulfur compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

thioadenosine (CHEBI:74046 )

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	0.42	ALOGPS
logP	-0.36	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	12.47	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	4	ChemAxon
Refractivity	78.83 m³·mol⁻¹	ChemAxon
Polarizability	31.6 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

DB07052

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

10041129

PDB ID

Not Available

ChEBI ID

74046

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5'-s-ethyl-5'-thioadenosine (NP0329330)

MOL for NP0329330 (5'-s-ethyl-5'-thioadenosine)

3D MOL for NP0329330 (5'-s-ethyl-5'-thioadenosine)

3D SDF for NP0329330 (5'-s-ethyl-5'-thioadenosine)

3D-SDF for NP0329330 (5'-s-ethyl-5'-thioadenosine)

PDB for NP0329330 (5'-s-ethyl-5'-thioadenosine)

3D PDB for NP0329330 (5'-s-ethyl-5'-thioadenosine)

SMILES for NP0329330 (5'-s-ethyl-5'-thioadenosine)

INCHI for NP0329330 (5'-s-ethyl-5'-thioadenosine)

Structure for NP0329330 (5'-s-ethyl-5'-thioadenosine)

3D Structure for NP0329330 (5'-s-ethyl-5'-thioadenosine)