MiMeDB: Showing metabocard for Cis-zeatin-9-N-glucoside (MMDBc0052955)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-05-16 21:10:03 UTC

Update Date

2024-04-30 20:45:05 UTC

Metabolite ID

MMDBc0052955

Metabolite Identification

Common Name

Cis-zeatin-9-N-glucoside

Description

cis-Zeatin-9-N-glucoside is an intermediate in cytokinins 9-N-glucoside biosynthesis. It is generated from cis-zeatin via the enzyme UDP glycosyltransferase. Glucosylation of cytokinins is a well-recognized modification that is thought to play an important role in hormonal homeostasis. Several types of cytokinins conjugation exist which render cytokinins inactive: O-xylosylation, O-glucosylation, and N-glucosylation.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241203492D          

 27 29  0  0  1  0            999 V2000
   10.4089  -12.9252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1234  -12.5127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1234  -11.6878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4089  -11.2753    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.6944  -11.6878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6944  -12.5127    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9081  -11.4328    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3925  -12.1003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9081  -12.7676    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1630  -10.6482    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.9700  -10.4770    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.2249   -9.6924    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.6728   -9.0790    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.8659   -9.2508    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.6109  -10.0354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3139   -8.6374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5069   -8.8092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9278   -8.2944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0318   -9.5206    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5220  -11.0899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4089  -13.7501    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.1234  -14.1626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1234  -14.9876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8380  -15.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8380  -16.2249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5519  -14.9876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5519  -14.1626    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  0  0  0  0
  1 21  1  0  0  0  0
  2  3  2  0  0  0  0
  2  9  1  0  0  0  0
  3  4  1  0  0  0  0
  3  7  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  7  8  1  0  0  0  0
 10  7  1  6  0  0  0
  8  9  2  0  0  0  0
 10 11  1  0  0  0  0
 10 15  1  0  0  0  0
 11 12  1  0  0  0  0
 11 20  1  6  0  0  0
 12 13  1  0  0  0  0
 12 19  1  1  0  0  0
 13 14  1  0  0  0  0
 13 18  1  6  0  0  0
 14 15  1  0  0  0  0
 14 16  1  1  0  0  0
 16 17  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
M  END


  Mrv0541 02241203492D          

 27 29  0  0  1  0            999 V2000
   10.4089  -12.9252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1234  -12.5127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1234  -11.6878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4089  -11.2753    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.6944  -11.6878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6944  -12.5127    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9081  -11.4328    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3925  -12.1003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9081  -12.7676    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1630  -10.6482    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.9700  -10.4770    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.2249   -9.6924    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.6728   -9.0790    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.8659   -9.2508    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.6109  -10.0354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3139   -8.6374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5069   -8.8092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9278   -8.2944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0318   -9.5206    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5220  -11.0899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4089  -13.7501    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.1234  -14.1626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1234  -14.9876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8380  -15.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8380  -16.2249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5519  -14.9876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5519  -14.1626    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  0  0  0  0
  1 21  1  0  0  0  0
  2  3  2  0  0  0  0
  2  9  1  0  0  0  0
  3  4  1  0  0  0  0
  3  7  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  7  8  1  0  0  0  0
 10  7  1  6  0  0  0
  8  9  2  0  0  0  0
 10 11  1  0  0  0  0
 10 15  1  0  0  0  0
 11 12  1  0  0  0  0
 11 20  1  6  0  0  0
 12 13  1  0  0  0  0
 12 19  1  1  0  0  0
 13 14  1  0  0  0  0
 13 18  1  6  0  0  0
 14 15  1  0  0  0  0
 14 16  1  1  0  0  0
 16 17  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0052955

> <DATABASE_NAME>
MIME

> <SMILES>
C\C(CO)=C\CNC1=NC=NC2=C1N=CN2[C@@H]1O[C@@H](CO)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C16H23N5O6/c1-8(4-22)2-3-17-14-10-15(19-6-18-14)21(7-20-10)16-13(26)12(25)11(24)9(5-23)27-16/h2,6-7,9,11-13,16,22-26H,3-5H2,1H3,(H,17,18,19)/b8-2-/t9-,11-,12+,13-,16+/m0/s1

> <INCHI_KEY>
VYRAJOITMBSQSE-UMNZXQRGSA-N

> <FORMULA>
C16H23N5O6

> <MOLECULAR_WEIGHT>
381.3837

> <EXACT_MASS>
381.164833493

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_AVERAGE_POLARIZABILITY>
38.34811437145662

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3S,4R,5R,6S)-2-(6-{[(2Z)-4-hydroxy-3-methylbut-2-en-1-yl]amino}-9H-purin-9-yl)-6-(hydroxymethyl)oxane-3,4,5-triol

> <ALOGPS_LOGP>
-0.71

> <JCHEM_LOGP>
-2.3391197993333335

> <ALOGPS_LOGS>
-1.77

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.267143683351048

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.357289457511548

> <JCHEM_PKA_STRONGEST_BASIC>
4.845278644206053

> <JCHEM_POLAR_SURFACE_AREA>
166.01

> <JCHEM_REFRACTIVITY>
95.54439999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.42e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3S,4R,5R,6S)-2-(6-{[(2Z)-4-hydroxy-3-methylbut-2-en-1-yl]amino}purin-9-yl)-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      19.430 -24.127   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      20.764 -23.357   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      20.764 -21.817   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0      19.430 -21.047   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      18.096 -21.817   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      18.096 -23.357   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0      22.228 -21.341   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      23.133 -22.587   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      22.228 -23.833   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      22.704 -19.877   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      24.211 -19.557   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      24.686 -18.092   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      23.656 -16.947   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      22.150 -17.268   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      21.674 -18.733   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      21.119 -16.123   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      19.613 -16.444   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      24.132 -15.483   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      26.193 -17.772   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      25.241 -20.701   0.000  0.00  0.00           O+0
HETATM   21  N   UNK     0      19.430 -25.667   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0      20.764 -26.437   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      20.764 -27.977   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      22.098 -28.747   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      22.098 -30.286   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      23.430 -27.977   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      23.430 -26.437   0.000  0.00  0.00           O+0
CONECT    1    2    6   21                                                  
CONECT    2    1    3    9                                                  
CONECT    3    2    4    7                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5                                                       
CONECT    7    3    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    2    8                                                       
CONECT   10    7   11   15                                                  
CONECT   11   10   12   20                                                  
CONECT   12   11   13   19                                                  
CONECT   13   12   14   18                                                  
CONECT   14   13   15   16                                                  
CONECT   15   10   14                                                       
CONECT   16   14   17                                                       
CONECT   17   16                                                            
CONECT   18   13                                                            
CONECT   19   12                                                            
CONECT   20   11                                                            
CONECT   21    1   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

Synonyms

Value	Source
(Z)-Zeatin-9-N-glucoside	HMDB

Molecular Formula

C₁₆H₂₃N₅O₆

Average Mass

381.3837

Monoisotopic Mass

381.164833493

IUPAC Name

(2R,3S,4R,5R,6S)-2-(6-{[(2Z)-4-hydroxy-3-methylbut-2-en-1-yl]amino}-9H-purin-9-yl)-6-(hydroxymethyl)oxane-3,4,5-triol

Traditional Name

(2R,3S,4R,5R,6S)-2-(6-{[(2Z)-4-hydroxy-3-methylbut-2-en-1-yl]amino}purin-9-yl)-6-(hydroxymethyl)oxane-3,4,5-triol

CAS Registry Number

Not Available

SMILES

C\C(CO)=C\CNC1=NC=NC2=C1N=CN2[C@@H]1O[C@@H](CO)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C16H23N5O6/c1-8(4-22)2-3-17-14-10-15(19-6-18-14)21(7-20-10)16-13(26)12(25)11(24)9(5-23)27-16/h2,6-7,9,11-13,16,22-26H,3-5H2,1H3,(H,17,18,19)/b8-2-/t9-,11-,12+,13-,16+/m0/s1

InChI Key

VYRAJOITMBSQSE-UMNZXQRGSA-N

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

Hexose monosaccharide
N-glycosyl compound
6-alkylaminopurine
6-aminopurine
Imidazopyrimidine
Purine
Aminopyrimidine
Secondary aliphatic/aromatic amine
Monosaccharide
N-substituted imidazole
Oxane
Pyrimidine
Imidolactam
Azole
Heteroaromatic compound
Imidazole
Secondary alcohol
Azacycle
Secondary amine
Polyol
Organoheterocyclic compound
Oxacycle
Primary alcohol
Organic nitrogen compound
Hydrocarbon derivative
Alcohol
Organopnictogen compound
Organonitrogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	6.42 g/L	ALOGPS
logP	-0.71	ALOGPS
logP	-2.3	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	12.36	ChemAxon
pKa (Strongest Basic)	4.85	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	166.01 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	95.54 m³·mol⁻¹	ChemAxon
Polarizability	38.35 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0mb9-5239000000-b8e0b261f8ee58a2dd25	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive	splash10-0zfr-2041039000-ad34fbc4e41ab60a2462	2017-10-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-1096000000-319d51660b2739efa9c8	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0uk9-2290000000-94c3eb1139ad0a41500b	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fl9-9560000000-ee5228b62b9043912d5e	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00lr-0089000000-4d48704d152e078a59a9	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0090000000-3793dcfc9505fc827456	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-1930000000-530373c21190b451775d	2017-09-01	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Basidiomycota	8	Human feces
Eukaryota/Fungi	Ascomycota	2

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

HMDB0012202

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB028848

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

53481386

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Wishart DS, Li C, Marcu A, Badran H, Pon A, Budinski Z, Patron J, Lipton D, Cao X, Oler E, Li K, Paccoud M, Hong C, Guo AC, Chan C, Wei W, Ramirez-Gaona M: PathBank: a comprehensive pathway database for model organisms. Nucleic Acids Res. 2020 Jan 8;48(D1):D470-D478. doi: 10.1093/nar/gkz861. [PubMed:31602464 ]
Yannai, Shmuel (2004). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. Boca Raton: Chapman & Hall/CRC..

Showing metabocard for Cis-zeatin-9-N-glucoside (MMDBc0052955)

MOL for #<Metabolite:0x00007fecd89f0bd8>

3D MOL for #<Metabolite:0x00007fecd89f0bd8>

3D SDF for #<Metabolite:0x00007fecd89f0bd8>

3D-SDF for #<Metabolite:0x00007fecd89f0bd8>

PDB for #<Metabolite:0x00007fecd89f0bd8>

3D PDB for #<Metabolite:0x00007fecd89f0bd8>

SMILES for #<Metabolite:0x00007fecd89f0bd8>

INCHI for #<Metabolite:0x00007fecd89f0bd8>

Structure for #<Metabolite:0x00007fecd89f0bd8>

3D Structure for #<Metabolite:0x00007fecd89f0bd8>