NP-MRD: Showing NP-Card for Catechin 7-xyloside (NP0046616)

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Record Information

Version

2.0

Created at

2022-03-17 20:08:48 UTC

Updated at

2022-03-17 20:08:48 UTC

NP-MRD ID

NP0046616

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Catechin 7-xyloside

Description

Catechin 7-xyloside is found in Betula davurica, Betula ermanii, Betula maximowicziana, Betula ovalifolia, Betula papyrifera, Betula pendula, Betula pubescens , Polypodium vulgare , Spiraea hypericifolia, Ulmus americana, Ulmus davidiana and Ulmus laevis.

Structure

MOL SDF PDB SMILES InChI

Structure #1
  Mrv0541 02241212292D          

 30 33  0  0  0  0            999 V2000
   -2.5929    0.4162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3073    0.8287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3073    1.6537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5929    2.0663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8784    1.6537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8784    0.8287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1639    0.4162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1639    2.0663    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4495    1.6537    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4495    0.8287    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2650    2.0662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9795    1.6537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2650    2.8913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9795    3.3038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6939    2.8913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6939    2.0662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5929   -0.4088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2650    0.4162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4084    3.3038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4084    1.6537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2593    2.7807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0843    2.7807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4968    2.0662    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.0843    1.3517    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.2593    1.3517    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.8468    2.0662    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0218    2.0662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8468    0.6373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3218    2.0662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4968    0.6372    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  1 17  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3 27  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  8  1  0  0  0  0
  6  7  1  0  0  0  0
  7 10  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  6  0  0  0
 10 18  1  1  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 12 16  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 19  1  0  0  0  0
 16 20  1  0  0  0  0
 21 22  1  0  0  0  0
 21 26  1  0  0  0  0
 22 23  1  0  0  0  0
 24 23  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  1  0  0  0
 25 28  1  6  0  0  0
 23 29  1  6  0  0  0
 24 30  1  1  0  0  0
M  END

Structure #1
  Mrv0541 02241212292D          

 30 33  0  0  0  0            999 V2000
   -2.5929    0.4162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3073    0.8287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3073    1.6537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5929    2.0663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8784    1.6537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8784    0.8287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1639    0.4162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1639    2.0663    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4495    1.6537    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4495    0.8287    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2650    2.0662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9795    1.6537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2650    2.8913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9795    3.3038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6939    2.8913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6939    2.0662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5929   -0.4088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2650    0.4162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4084    3.3038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4084    1.6537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2593    2.7807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0843    2.7807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4968    2.0662    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.0843    1.3517    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.2593    1.3517    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.8468    2.0662    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0218    2.0662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8468    0.6373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3218    2.0662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4968    0.6372    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  1 17  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3 27  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  8  1  0  0  0  0
  6  7  1  0  0  0  0
  7 10  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  6  0  0  0
 10 18  1  1  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 12 16  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 19  1  0  0  0  0
 16 20  1  0  0  0  0
 21 22  1  0  0  0  0
 21 26  1  0  0  0  0
 22 23  1  0  0  0  0
 24 23  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  1  0  0  0
 25 28  1  6  0  0  0
 23 29  1  6  0  0  0
 24 30  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0046616

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]1CO[C@@H](OC2=CC3=C(C[C@H](O)[C@H](O3)C3=CC(O)=C(O)C=C3)C(O)=C2)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C20H22O10/c21-11-2-1-8(3-13(11)23)19-14(24)6-10-12(22)4-9(5-16(10)30-19)29-20-18(27)17(26)15(25)7-28-20/h1-5,14-15,17-27H,6-7H2/t14-,15+,17-,18+,19+,20-/m0/s1

> <INCHI_KEY>
UQKKDJWFQBNZBJ-MLYGIHNMSA-N

> <FORMULA>
C20H22O10

> <MOLECULAR_WEIGHT>
422.3827

> <EXACT_MASS>
422.121296924

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_AVERAGE_POLARIZABILITY>
41.11590728480705

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3R,4S,5R)-2-{[(2R,3S)-2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-3,4-dihydro-2H-1-benzopyran-7-yl]oxy}oxane-3,4,5-triol

> <ALOGPS_LOGP>
-0.22

> <JCHEM_LOGP>
0.1573738639999997

> <ALOGPS_LOGS>
-2.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.704018454785794

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.0411368106256

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2921294530506104

> <JCHEM_POLAR_SURFACE_AREA>
169.29999999999998

> <JCHEM_REFRACTIVITY>
100.18159999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.58e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(+)-catechin 7-O-β-D-xyloside

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Structure #1                                      
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -4.840   0.777   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.174   1.547   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.174   3.087   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.840   3.857   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.506   3.087   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.506   1.547   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.173   0.777   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -2.173   3.857   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -0.839   3.087   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.839   1.547   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.495   3.857   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.828   3.087   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.495   5.397   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.828   6.167   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.162   5.397   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.162   3.857   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -4.840  -0.763   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.495   0.777   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       4.496   6.167   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       4.496   3.087   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -9.817   5.191   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0     -11.357   5.191   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0     -12.127   3.857   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -11.357   2.523   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -9.817   2.523   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -9.047   3.857   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -7.507   3.857   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -9.047   1.190   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0     -13.667   3.857   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0     -12.127   1.189   0.000  0.00  0.00           O+0
CONECT    1    2    6   17                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   27                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    1    5    7                                                  
CONECT    7    6   10                                                       
CONECT    8    5    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    7    9   18                                                  
CONECT   11    9   12   13                                                  
CONECT   12   11   16                                                       
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   19                                                  
CONECT   16   12   15   20                                                  
CONECT   17    1                                                            
CONECT   18   10                                                            
CONECT   19   15                                                            
CONECT   20   16                                                            
CONECT   21   22   26                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   29                                                  
CONECT   24   23   25   30                                                  
CONECT   25   24   26   28                                                  
CONECT   26   21   25   27                                                  
CONECT   27    3   26                                                       
CONECT   28   25                                                            
CONECT   29   23                                                            
CONECT   30   24                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Value	Source
Catechin 7-O-beta-D-xyloside	ChEBI
Catechin 7-O-b-D-xyloside	Generator
Catechin 7-O-β-D-xyloside	Generator

Chemical Formula

C₂₀H₂₂O₁₀

Average Mass

422.3827 Da

Monoisotopic Mass

422.12130 Da

IUPAC Name

(2S,3R,4S,5R)-2-{[(2R,3S)-2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-3,4-dihydro-2H-1-benzopyran-7-yl]oxy}oxane-3,4,5-triol

Traditional Name

(+)-catechin 7-O-β-D-xyloside

CAS Registry Number

65597-47-9

SMILES

O[C@@H]1CO[C@@H](OC2=CC3=C(C[C@H](O)[C@H](O3)C3=CC(O)=C(O)C=C3)C(O)=C2)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C20H22O10/c21-11-2-1-8(3-13(11)23)19-14(24)6-10-12(22)4-9(5-16(10)30-19)29-20-18(27)17(26)15(25)7-28-20/h1-5,14-15,17-27H,6-7H2/t14-,15+,17-,18+,19+,20-/m0/s1

InChI Key

UQKKDJWFQBNZBJ-MLYGIHNMSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Betula davurica	LOTUS Database	35616633
Betula ermanii	Plant	KNApSAcK
Betula maximowicziana	LOTUS Database	35616633
Betula ovalifolia	LOTUS Database	35616633
Betula papyrifera	Plant	KNApSAcK
Betula pendula	LOTUS Database	35616633
Betula pubescens	Plant	KNApSAcK
Corylus avellana	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Polypodium vulgare	Plant	KNApSAcK
Spiraea hypericifolia	Plant	KNApSAcK
Ulmus americana	Plant	KNApSAcK
Ulmus davidiana	LOTUS Database	35616633
Ulmus laevis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-7-O-glycosides

Alternative Parents

Substituents

Flavonoid-7-o-glycoside
Catechin
3'-hydroxyflavonoid
3-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
Flavan-3-ol
Hydroxyflavonoid
Flavan
Phenolic glycoside
Glycosyl compound
O-glycosyl compound
Chromane
Benzopyran
1-benzopyran
Pentose monosaccharide
Catechol
Phenol
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Oxane
Monosaccharide
Monocyclic benzene moiety
Benzenoid
Secondary alcohol
Polyol
Acetal
Oxacycle
Ether
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Alcohol
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

monosaccharide derivative (CHEBI:28117 )
beta-D-xyloside (CHEBI:28117 )
Flavans, Flavanols and Leucoanthocyanidins (C09617 )
Flavan 3-ols (C09617 )

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	-0.22	ALOGPS
logP	0.16	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	9.04	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	169.3 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	100.18 m³·mol⁻¹	ChemAxon
Polarizability	41.12 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB005209

KNApSAcK ID

C00008852

Chemspider ID

Not Available

KEGG Compound ID

C09617

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

73533

PDB ID

Not Available

ChEBI ID

28117

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Catechin 7-xyloside (NP0046616)

MOL for NP0046616 (Catechin 7-xyloside)

3D MOL for NP0046616 (Catechin 7-xyloside)

3D SDF for NP0046616 (Catechin 7-xyloside)

3D-SDF for NP0046616 (Catechin 7-xyloside)

PDB for NP0046616 (Catechin 7-xyloside)

3D PDB for NP0046616 (Catechin 7-xyloside)

SMILES for NP0046616 (Catechin 7-xyloside)

INCHI for NP0046616 (Catechin 7-xyloside)

Structure for NP0046616 (Catechin 7-xyloside)

3D Structure for NP0046616 (Catechin 7-xyloside)