MiMeDB: Showing metabocard for Cis-zeatin-7-N-glucoside (MMDBc0052954)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-05-16 21:10:01 UTC

Update Date

2024-04-30 20:44:58 UTC

Metabolite ID

MMDBc0052954

Metabolite Identification

Common Name

Cis-zeatin-7-N-glucoside

Description

Cis-zeatin-7-N-glucoside, also known as raphanatin, 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). Cis-zeatin-7-N-glucoside is a very strong basic compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652303112020092D          

 27 29  0  0  0  0            999 V2000
 9991.7001 9990.7689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.9858 9990.3565    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9990.9858 9989.5315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9991.7001 9989.1190    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9992.4147 9990.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.4147 9989.5315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.1992 9989.2766    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9993.6840 9989.9439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.1589 9990.6267    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9993.1959 9994.2225    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9994.5008 9993.6411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9994.7998 9990.7992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.4708 9992.3067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9992.8603 9993.4688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.0095 9992.0478    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9993.3452 9992.8014    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9994.1655 9992.8877    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9994.6504 9992.2203    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9994.3149 9991.4667    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9993.4944 9991.3805    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9991.7001 9991.5953    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9990.9860 9992.0081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.2710 9991.5953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9989.5561 9992.0081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9988.8409 9991.5953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9989.5561 9992.8338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9988.1259 9992.0081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  4  6  2  0  0  0  0
  1  5  2  0  0  0  0
 14 10  1  0  0  0  0
 16 14  1  6  0  0  0
 16 15  1  0  0  0  0
 17 11  1  1  0  0  0
 17 16  1  0  0  0  0
 18 13  1  6  0  0  0
 18 17  1  0  0  0  0
 19 12  1  1  0  0  0
 19 18  1  0  0  0  0
 20 15  1  0  0  0  0
 20 19  1  0  0  0  0
 20  9  1  6  0  0  0
  9  5  1  0  0  0  0
  9  8  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
 25 27  1  0  0  0  0
 21  1  1  0  0  0  0
M  END


  Mrv1652303112020092D          

 27 29  0  0  0  0            999 V2000
 9991.7001 9990.7689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.9858 9990.3565    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9990.9858 9989.5315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9991.7001 9989.1190    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9992.4147 9990.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.4147 9989.5315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.1992 9989.2766    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9993.6840 9989.9439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.1589 9990.6267    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9993.1959 9994.2225    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9994.5008 9993.6411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9994.7998 9990.7992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.4708 9992.3067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9992.8603 9993.4688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.0095 9992.0478    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9993.3452 9992.8014    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9994.1655 9992.8877    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9994.6504 9992.2203    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9994.3149 9991.4667    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9993.4944 9991.3805    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9991.7001 9991.5953    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9990.9860 9992.0081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.2710 9991.5953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9989.5561 9992.0081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9988.8409 9991.5953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9989.5561 9992.8338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9988.1259 9992.0081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  4  6  2  0  0  0  0
  1  5  2  0  0  0  0
 14 10  1  0  0  0  0
 16 14  1  6  0  0  0
 16 15  1  0  0  0  0
 17 11  1  1  0  0  0
 17 16  1  0  0  0  0
 18 13  1  6  0  0  0
 18 17  1  0  0  0  0
 19 12  1  1  0  0  0
 19 18  1  0  0  0  0
 20 15  1  0  0  0  0
 20 19  1  0  0  0  0
 20  9  1  6  0  0  0
  9  5  1  0  0  0  0
  9  8  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
 25 27  1  0  0  0  0
 21  1  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0052954

> <DATABASE_NAME>
MIME

> <SMILES>
C\C(CO)=C/CNC1=C2N(C=NC2=NC=N1)[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)20-7-21(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-/m1/s1

> <INCHI_KEY>
HTDHRCLVWUEXIS-HNVSNYHQSA-N

> <FORMULA>
C16H23N5O6

> <MOLECULAR_WEIGHT>
381.3837

> <EXACT_MASS>
381.164833493

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
36.454374883162316

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R,4S,5S,6R)-2-(6-{[(2E)-4-hydroxy-3-methylbut-2-en-1-yl]amino}-7H-purin-7-yl)-6-(hydroxymethyl)oxane-3,4,5-triol

> <ALOGPS_LOGP>
-0.73

> <JCHEM_LOGP>
-2.3815772999999996

> <ALOGPS_LOGS>
-1.75

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.267853558127669

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.358459084892697

> <JCHEM_PKA_STRONGEST_BASIC>
3.303007474354502

> <JCHEM_POLAR_SURFACE_AREA>
166.01

> <JCHEM_REFRACTIVITY>
97.16459999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.78e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
trans-zeatin-7-β-D-glucoside

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-MAR-20         0                                  
HETATM    1  C   UNK     0    8651.1748649.435   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0    8649.8408648.665   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0    8649.8408647.125   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0    8651.1748646.355   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0    8652.5078648.665   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8652.5078647.125   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0    8653.9728646.650   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0    8654.8778647.895   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0    8653.8978649.170   0.000  0.00  0.00           N+0
HETATM   10  O   UNK     0    8653.9668655.882   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0    8656.4028654.797   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0    8656.9608649.492   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0    8658.2128652.306   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0    8653.3398654.475   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0    8653.6188651.823   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0    8654.2448653.229   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8655.7768653.390   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8656.6818652.145   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8656.0548650.738   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8654.5238650.577   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0    8651.1748650.978   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0    8649.8418651.748   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8648.5068650.978   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8647.1718651.748   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8645.8368650.978   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8647.1718653.290   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0    8644.5028651.748   0.000  0.00  0.00           O+0
CONECT    1    2    5   21                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    6                                                       
CONECT    5    6    1    9                                                  
CONECT    6    5    7    4                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9   20    5    8                                                  
CONECT   10   14                                                            
CONECT   11   17                                                            
CONECT   12   19                                                            
CONECT   13   18                                                            
CONECT   14   10   16                                                       
CONECT   15   16   20                                                       
CONECT   16   14   15   17                                                  
CONECT   17   11   16   18                                                  
CONECT   18   13   17   19                                                  
CONECT   19   12   18   20                                                  
CONECT   20   15   19    9                                                  
CONECT   21   22    1                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24   27                                                       
CONECT   26   24                                                            
CONECT   27   25                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

Synonyms

Value	Source
(Z)-Zeatin-7-N-glucoside	HMDB
7-beta-D-Glucopyranosylzeatin	HMDB
Raphanatin	HMDB

Molecular Formula

C₁₆H₂₃N₅O₆

Average Mass

381.3837

Monoisotopic Mass

381.164833493

IUPAC Name

(2R,3R,4S,5S,6R)-2-(6-{[(2E)-4-hydroxy-3-methylbut-2-en-1-yl]amino}-7H-purin-7-yl)-6-(hydroxymethyl)oxane-3,4,5-triol

Traditional Name

trans-zeatin-7-β-D-glucoside

CAS Registry Number

Not Available

SMILES

C\C(CO)=C/CNC1=C2N(C=NC2=NC=N1)[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)20-7-21(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-/m1/s1

InChI Key

HTDHRCLVWUEXIS-HNVSNYHQSA-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

N-glycosyl compound (CHEBI:80494 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	6.78 g/L	ALOGPS
logP	-0.73	ALOGPS
logP	-2.4	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	12.36	ChemAxon
pKa (Strongest Basic)	3.3	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	97.16 m³·mol⁻¹	ChemAxon
Polarizability	36.45 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	splash10-0mb9-5239000000-5a39e73e49156d9e42bb	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive	splash10-0zfr-2310049000-b1706c1a26573bfff619	2017-10-06	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-004i-0093000000-caff95a98241fa3bf4e0	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-001i-0009000000-8fb3524f004bf5accaaf	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-014i-0090000000-1840e64e915b680979e3	2017-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0230-1079000000-ebe0f3ec2a5f52f0e89a	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0uk9-4291000000-35c2f9d89c37905be56e	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fl9-9550000000-36f89df4a8f7d824abd4	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00lr-0089000000-1a3c940eab5f9c3ae2a5	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0190000000-4a7a6ea52eda2ee47d52	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-1920000000-a8e56e3ce9ee6bf98929	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

HMDB0012201

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB028847

KNApSAcK ID

Not Available

Chemspider ID

4952889

KEGG Compound ID

C16443

BioCyc ID

CPD-4612

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6450275

PDB ID

Not Available

ChEBI ID

80494

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 ]

Showing metabocard for Cis-zeatin-7-N-glucoside (MMDBc0052954)

MOL for #<Metabolite:0x00007fecda3b6338>

3D MOL for #<Metabolite:0x00007fecda3b6338>

3D SDF for #<Metabolite:0x00007fecda3b6338>

3D-SDF for #<Metabolite:0x00007fecda3b6338>

PDB for #<Metabolite:0x00007fecda3b6338>

3D PDB for #<Metabolite:0x00007fecda3b6338>

SMILES for #<Metabolite:0x00007fecda3b6338>

INCHI for #<Metabolite:0x00007fecda3b6338>

Structure for #<Metabolite:0x00007fecda3b6338>

3D Structure for #<Metabolite:0x00007fecda3b6338>