NP-MRD: Showing NP-Card for methyl 5-(6-aminopurin-9-yl)-1,4,12-trihydroxy-13-[(2-methylbut-2-enoyl)oxy]-2,6,10-trioxatricyclo[7.4.0.0³,⁷]tridecane-11-carboxylate (NP0296365)

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Record Information

Version

2.0

Created at

2022-09-10 05:53:51 UTC

Updated at

2022-09-10 05:53:52 UTC

NP-MRD ID

NP0296365

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 5-(6-aminopurin-9-yl)-1,4,12-trihydroxy-13-[(2-methylbut-2-enoyl)oxy]-2,6,10-trioxatricyclo[7.4.0.0³,⁷]tridecane-11-carboxylate

Description

Methyl 5-(6-amino-9H-purin-9-yl)-1,4,12-trihydroxy-13-[(2-methylbut-2-enoyl)oxy]-2,6,10-trioxatricyclo[7.4.0.0³,⁷]Tridecane-11-carboxylate belongs to the class of organic compounds known as glycosylamines. Glycosylamines are compounds consisting of an amine with a beta-N-glycosidic bond to a carbohydrate, thus forming a cyclic hemiaminal ether bond (alpha-amino ether). Based on a literature review very few articles have been published on methyl 5-(6-amino-9H-purin-9-yl)-1,4,12-trihydroxy-13-[(2-methylbut-2-enoyl)oxy]-2,6,10-trioxatricyclo[7.4.0.0³,⁷]Tridecane-11-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102207532D          

 37 41  0  0  0  0            999 V2000
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   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    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.3570   -1.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1434   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  4  0  0  0
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 17 36  1  0  0  0  0
  8 36  1  0  0  0  0
 36 37  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309102207532D          

 37 41  0  0  0  0            999 V2000
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 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 17 36  1  0  0  0  0
  8 36  1  0  0  0  0
 36 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0296365

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1OC2CC3OC(C(O)C3OC2(O)C(OC(=O)C(C)=CC)C1O)N1C=NC2=C(N)N=CN=C12

> <INCHI_IDENTIFIER>
InChI=1S/C22H27N5O10/c1-4-8(2)20(30)36-16-12(28)15(21(31)33-3)35-10-5-9-14(37-22(10,16)32)13(29)19(34-9)27-7-26-11-17(23)24-6-25-18(11)27/h4,6-7,9-10,12-16,19,28-29,32H,5H2,1-3H3,(H2,23,24,25)

> <INCHI_KEY>
LUHFPLRYWUPHKS-UHFFFAOYSA-N

> <FORMULA>
C22H27N5O10

> <MOLECULAR_WEIGHT>
521.483

> <EXACT_MASS>
521.175792089

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
49.33474567599923

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 5-(6-amino-9H-purin-9-yl)-1,4,12-trihydroxy-13-[(2-methylbut-2-enoyl)oxy]-2,6,10-trioxatricyclo[7.4.0.0^{3,7}]tridecane-11-carboxylate

> <JCHEM_LOGP>
-0.36984991099999887

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.40760790731974

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.092158196715602

> <JCHEM_PKA_STRONGEST_BASIC>
3.9212922659418066

> <JCHEM_POLAR_SURFACE_AREA>
210.59999999999994

> <JCHEM_REFRACTIVITY>
120.78690000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
methyl 5-(6-aminopurin-9-yl)-1,4,12-trihydroxy-13-[(2-methylbut-2-enoyl)oxy]-2,6,10-trioxatricyclo[7.4.0.0^{3,7}]tridecane-11-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       8.133  -0.294   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       9.038  -1.540   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0      10.578  -1.540   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0      11.483  -0.294   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0      12.948  -0.770   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0      12.948  -2.310   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      14.092  -3.340   0.000  0.00  0.00           C+0
HETATM   27  N   UNK     0      15.557  -2.865   0.000  0.00  0.00           N+0
HETATM   28  N   UNK     0      13.772  -4.847   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0      12.308  -5.323   0.000  0.00  0.00           C+0
HETATM   30  N   UNK     0      11.163  -4.292   0.000  0.00  0.00           N+0
HETATM   31  C   UNK     0      11.483  -2.786   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.133  -2.786   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       8.609  -4.251   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       4.001  -3.850   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   36                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   16                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14                                                            
CONECT   16   11   17                                                       
CONECT   17   16   18   36                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   34                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   32                                                  
CONECT   22   21   23   31                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   31                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   25   22                                                  
CONECT   32   21   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   19   35                                                  
CONECT   35   34   36                                                       
CONECT   36   35   17    8   37                                             
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   82    0
END

View in JSmol

Synonyms

Value	Source
Methyl 5-(6-amino-9H-purin-9-yl)-1,4,12-trihydroxy-13-[(2-methylbut-2-enoyl)oxy]-2,6,10-trioxatricyclo[7.4.0.0,]tridecane-11-carboxylic acid	Generator

Chemical Formula

C₂₂H₂₇N₅O₁₀

Average Mass

521.4830 Da

Monoisotopic Mass

521.17579 Da

IUPAC Name

methyl 5-(6-amino-9H-purin-9-yl)-1,4,12-trihydroxy-13-[(2-methylbut-2-enoyl)oxy]-2,6,10-trioxatricyclo[7.4.0.0^{3,7}]tridecane-11-carboxylate

Traditional Name

methyl 5-(6-aminopurin-9-yl)-1,4,12-trihydroxy-13-[(2-methylbut-2-enoyl)oxy]-2,6,10-trioxatricyclo[7.4.0.0^{3,7}]tridecane-11-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1OC2CC3OC(C(O)C3OC2(O)C(OC(=O)C(C)=CC)C1O)N1C=NC2=C(N)N=CN=C12

InChI Identifier

InChI=1S/C22H27N5O10/c1-4-8(2)20(30)36-16-12(28)15(21(31)33-3)35-10-5-9-14(37-22(10,16)32)13(29)19(34-9)27-7-26-11-17(23)24-6-25-18(11)27/h4,6-7,9-10,12-16,19,28-29,32H,5H2,1-3H3,(H2,23,24,25)

InChI Key

LUHFPLRYWUPHKS-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glycosylamines. Glycosylamines are compounds consisting of an amine with a beta-N-glycosidic bond to a carbohydrate, thus forming a cyclic hemiaminal ether bond (alpha-amino ether).

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Glycosylamines

Alternative Parents

Substituents

C-glycosyl compound
Disaccharide
N-glycosyl compound
6-aminopurine
Purine
Imidazopyrimidine
Furopyran
Aminopyrimidine
Beta-hydroxy acid
Fatty acid ester
Imidolactam
Hydroxy acid
Fatty acyl
N-substituted imidazole
Oxane
Pyrimidine
Pyran
Dicarboxylic acid or derivatives
Azole
Heteroaromatic compound
Furan
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Imidazole
Methyl ester
Tetrahydrofuran
Hemiacetal
Amino acid or derivatives
Secondary alcohol
Carboxylic acid ester
Polyol
Organoheterocyclic compound
Carboxylic acid derivative
Dialkyl ether
Oxacycle
Ether
Azacycle
Carbonyl group
Hydrocarbon derivative
Organopnictogen compound
Primary amine
Amine
Organonitrogen compound
Alcohol
Organic oxide
Organic nitrogen 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	-0.37	ChemAxon
pKa (Strongest Acidic)	10.09	ChemAxon
pKa (Strongest Basic)	3.92	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	210.6 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	120.79 m³·mol⁻¹	ChemAxon
Polarizability	49.33 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

162857084

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 5-(6-aminopurin-9-yl)-1,4,12-trihydroxy-13-[(2-methylbut-2-enoyl)oxy]-2,6,10-trioxatricyclo[7.4.0.0³,⁷]tridecane-11-carboxylate (NP0296365)

MOL for NP0296365 (methyl 5-(6-aminopurin-9-yl)-1,4,12-trihydroxy-13-[(2-methylbut-2-enoyl)oxy]-2,6,10-trioxatricyclo[7.4.0.0³,⁷]tridecane-11-carboxylate)

3D MOL for NP0296365 (methyl 5-(6-aminopurin-9-yl)-1,4,12-trihydroxy-13-[(2-methylbut-2-enoyl)oxy]-2,6,10-trioxatricyclo[7.4.0.0³,⁷]tridecane-11-carboxylate)

3D SDF for NP0296365 (methyl 5-(6-aminopurin-9-yl)-1,4,12-trihydroxy-13-[(2-methylbut-2-enoyl)oxy]-2,6,10-trioxatricyclo[7.4.0.0³,⁷]tridecane-11-carboxylate)

3D-SDF for NP0296365 (methyl 5-(6-aminopurin-9-yl)-1,4,12-trihydroxy-13-[(2-methylbut-2-enoyl)oxy]-2,6,10-trioxatricyclo[7.4.0.0³,⁷]tridecane-11-carboxylate)

PDB for NP0296365 (methyl 5-(6-aminopurin-9-yl)-1,4,12-trihydroxy-13-[(2-methylbut-2-enoyl)oxy]-2,6,10-trioxatricyclo[7.4.0.0³,⁷]tridecane-11-carboxylate)

3D PDB for NP0296365 (methyl 5-(6-aminopurin-9-yl)-1,4,12-trihydroxy-13-[(2-methylbut-2-enoyl)oxy]-2,6,10-trioxatricyclo[7.4.0.0³,⁷]tridecane-11-carboxylate)

SMILES for NP0296365 (methyl 5-(6-aminopurin-9-yl)-1,4,12-trihydroxy-13-[(2-methylbut-2-enoyl)oxy]-2,6,10-trioxatricyclo[7.4.0.0³,⁷]tridecane-11-carboxylate)

INCHI for NP0296365 (methyl 5-(6-aminopurin-9-yl)-1,4,12-trihydroxy-13-[(2-methylbut-2-enoyl)oxy]-2,6,10-trioxatricyclo[7.4.0.0³,⁷]tridecane-11-carboxylate)

Structure for NP0296365 (methyl 5-(6-aminopurin-9-yl)-1,4,12-trihydroxy-13-[(2-methylbut-2-enoyl)oxy]-2,6,10-trioxatricyclo[7.4.0.0³,⁷]tridecane-11-carboxylate)

3D Structure for NP0296365 (methyl 5-(6-aminopurin-9-yl)-1,4,12-trihydroxy-13-[(2-methylbut-2-enoyl)oxy]-2,6,10-trioxatricyclo[7.4.0.0³,⁷]tridecane-11-carboxylate)