NP-MRD: Showing NP-Card for Zeatin-9-glucoside-O-glucoside (NP0055009)

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Record Information

Version

2.0

Created at

2022-04-28 01:11:04 UTC

Updated at

2022-04-28 01:11:04 UTC

NP-MRD ID

NP0055009

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Zeatin-9-glucoside-O-glucoside

Description

(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-(6-{[(2E)-3-methyl-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}but-2-en-1-yl]amino}-9H-purin-9-yl)oxane-3,4,5-triol belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol. Zeatin-9-glucoside-O-glucoside is found in Arabidopsis thaliana. Based on a literature review very few articles have been published on (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-(6-{[(2E)-3-methyl-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}but-2-en-1-yl]amino}-9H-purin-9-yl)oxane-3,4,5-triol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282203112D          

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M  END

     RDKit          3D

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M  END


  Mrv1652304282203112D          

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  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  1  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 13  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 14 19  1  0  0  0  0
 18 20  1  1  0  0  0
 20 21  1  0  0  0  0
 17 22  1  6  0  0  0
 16 23  1  1  0  0  0
 15 24  1  6  0  0  0
  2 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
  1 27  1  0  0  0  0
 28 25  1  1  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 28 33  1  0  0  0  0
 32 34  1  1  0  0  0
 34 35  1  0  0  0  0
 31 36  1  6  0  0  0
 30 37  1  1  0  0  0
 29 38  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0055009

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C(CO[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)=C/CNC1=C2N=CN([C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)C2=NC=N1

> <INCHI_IDENTIFIER>
InChI=1S/C22H33N5O11/c1-9(6-36-22-18(35)16(33)14(31)11(5-29)38-22)2-3-23-19-12-20(25-7-24-19)27(8-26-12)21-17(34)15(32)13(30)10(4-28)37-21/h2,7-8,10-11,13-18,21-22,28-35H,3-6H2,1H3,(H,23,24,25)/b9-2+/t10-,11-,13-,14-,15+,16+,17-,18-,21-,22+/m1/s1

> <INCHI_KEY>
DTPCZPXFOQSQNC-MMHCNIRFSA-N

> <FORMULA>
C22H33N5O11

> <MOLECULAR_WEIGHT>
543.53

> <EXACT_MASS>
543.217656903

> <JCHEM_ACCEPTOR_COUNT>
15

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
54.77051735378957

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-(6-{[(2E)-3-methyl-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}but-2-en-1-yl]amino}-9H-purin-9-yl)oxane-3,4,5-triol

> <ALOGPS_LOGP>
-1.36

> <JCHEM_LOGP>
-4.109955445000001

> <ALOGPS_LOGS>
-1.87

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.576777854354365

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.016730180273138

> <JCHEM_PKA_STRONGEST_BASIC>
3.701553964076777

> <JCHEM_POLAR_SURFACE_AREA>
245.16

> <JCHEM_REFRACTIVITY>
127.95769999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.27e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-(6-{[(2E)-3-methyl-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}but-2-en-1-yl]amino}purin-9-yl)oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       1.197  -2.073   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.197  -0.533   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       2.530   0.237   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       3.864  -0.533   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       3.864  -2.073   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       2.530  -2.843   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       2.530  -4.383   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       3.864  -5.153   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.864  -6.693   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.530  -7.463   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.197  -6.693   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.530  -9.003   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.197  -9.773   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.197 -11.313   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.530 -12.083   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.530 -13.623   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.197 -14.393   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.137 -13.623   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.137 -12.083   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -1.471 -14.393   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -1.471 -15.933   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       1.197 -15.933   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       3.864 -14.393   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       3.864 -11.313   0.000  0.00  0.00           O+0
HETATM   25  N   UNK     0      -0.268  -0.057   0.000  0.00  0.00           N+0
HETATM   26  C   UNK     0      -1.173  -1.303   0.000  0.00  0.00           C+0
HETATM   27  N   UNK     0      -0.268  -2.549   0.000  0.00  0.00           N+0
HETATM   28  C   UNK     0      -0.744   1.408   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.250   1.728   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.726   3.192   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.696   4.337   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.189   4.017   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       0.287   2.552   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       0.841   5.161   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       0.365   6.626   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      -2.171   5.802   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      -4.232   3.513   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      -3.281   0.583   0.000  0.00  0.00           O+0
CONECT    1    2    6   27                                                  
CONECT    2    1    3   25                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16   24                                                  
CONECT   16   15   17   23                                                  
CONECT   17   16   18   22                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18   14                                                       
CONECT   20   18   21                                                       
CONECT   21   20                                                            
CONECT   22   17                                                            
CONECT   23   16                                                            
CONECT   24   15                                                            
CONECT   25    2   26   28                                                  
CONECT   26   25   27                                                       
CONECT   27   26    1                                                       
CONECT   28   25   29   33                                                  
CONECT   29   28   30   38                                                  
CONECT   30   29   31   37                                                  
CONECT   31   30   32   36                                                  
CONECT   32   31   33   34                                                  
CONECT   33   32   28                                                       
CONECT   34   32   35                                                       
CONECT   35   34                                                            
CONECT   36   31                                                            
CONECT   37   30                                                            
CONECT   38   29                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₃₃N₅O₁₁

Average Mass

543.5300 Da

Monoisotopic Mass

543.21766 Da

IUPAC Name

(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-(6-{[(2E)-3-methyl-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}but-2-en-1-yl]amino}-9H-purin-9-yl)oxane-3,4,5-triol

Traditional Name

(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-(6-{[(2E)-3-methyl-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}but-2-en-1-yl]amino}purin-9-yl)oxane-3,4,5-triol

CAS Registry Number

Not Available

SMILES

C\C(CO[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)=C/CNC1=C2N=CN([C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)C2=NC=N1

InChI Identifier

InChI=1S/C22H33N5O11/c1-9(6-36-22-18(35)16(33)14(31)11(5-29)38-22)2-3-23-19-12-20(25-7-24-19)27(8-26-12)21-17(34)15(32)13(30)10(4-28)37-21/h2,7-8,10-11,13-18,21-22,28-35H,3-6H2,1H3,(H,23,24,25)/b9-2+/t10-,11-,13-,14-,15+,16+,17-,18-,21-,22+/m1/s1

InChI Key

DTPCZPXFOQSQNC-MMHCNIRFSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Arabidopsis thaliana	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl glycosides

Direct Parent

Fatty acyl glycosides of mono- and disaccharides

Alternative Parents

Substituents

Fatty acyl glycoside of mono- or disaccharide
Alkyl glycoside
6-alkylaminopurine
O-glycosyl compound
N-glycosyl compound
Glycosyl compound
6-aminopurine
Purine
Imidazopyrimidine
Secondary aliphatic/aromatic amine
Aminopyrimidine
Imidolactam
Pyrimidine
Oxane
N-substituted imidazole
Monosaccharide
Heteroaromatic compound
Imidazole
Azole
Secondary alcohol
Oxacycle
Azacycle
Organoheterocyclic compound
Secondary amine
Polyol
Acetal
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Organonitrogen compound
Amine
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	-1.4	ALOGPS
logP	-4.1	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	12.02	ChemAxon
pKa (Strongest Basic)	3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	245.16 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	127.96 m³·mol⁻¹	ChemAxon
Polarizability	54.77 Å³	ChemAxon
Number of Rings	4	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

163052638

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Zeatin-9-glucoside-O-glucoside (NP0055009)

MOL for NP0055009 (Zeatin-9-glucoside-O-glucoside)

3D MOL for NP0055009 (Zeatin-9-glucoside-O-glucoside)

3D SDF for NP0055009 (Zeatin-9-glucoside-O-glucoside)

3D-SDF for NP0055009 (Zeatin-9-glucoside-O-glucoside)

PDB for NP0055009 (Zeatin-9-glucoside-O-glucoside)

3D PDB for NP0055009 (Zeatin-9-glucoside-O-glucoside)

SMILES for NP0055009 (Zeatin-9-glucoside-O-glucoside)

INCHI for NP0055009 (Zeatin-9-glucoside-O-glucoside)

Structure for NP0055009 (Zeatin-9-glucoside-O-glucoside)

3D Structure for NP0055009 (Zeatin-9-glucoside-O-glucoside)