NP-MRD: Showing NP-Card for Benzyl 6-O-beta-D-apiofuranosyl-beta-D-glucoside (NP0047146)

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Record Information

Version

2.0

Created at

2022-03-17 20:35:24 UTC

Updated at

2022-03-17 20:35:24 UTC

NP-MRD ID

NP0047146

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Benzyl 6-O-beta-D-apiofuranosyl-beta-D-glucoside

Description

Benzyl 6-O-beta-D-apiofuranosyl-beta-D-glucoside is found in Anethum graveolens , Atractylodes japonica, Atractylodes lancea , Betula maximowicziana, Bretschneidera sinensis, Breynia rostrata, Bupleurum falcatum L. , Camellia sinensis, Canthium berberidifolium, Chrysanthemum zawadskii, Coriandrum sativum , Crepidiastrum lanceolatum, Foeniculum vulgare, Glehnia littoralis , Glochidion rubrum, Grevillea robusta, Helichrysum arenarium, Holmskioldia sanguinea, Hydrangea macrophylla, Petroselinum crispum, Pimpinella anisum L. , Piper retrofractum, Pyrus bourgaeana, Salvia officinalis, Sambucus nigra , Schefflera rotundifolia, Youngia japonica and Zanthoxylum piperitum.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241212592D          

 28 30  0  0  0  0            999 V2000
    1.9446   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2302   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2302   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9446   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6591   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6591   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5157   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2232   -0.8012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8906   -1.2862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6357   -2.0708    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.8107   -2.0708    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5557   -1.2862    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7711   -1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6357   -2.8958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8107   -2.8958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4505   -2.1998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9697   -1.5587    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6277   -0.6187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3422   -1.0312    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3422   -1.8563    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6277   -2.2688    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9132   -1.8563    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9132   -1.0312    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1988   -0.6187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1988   -2.2688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0566   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0566   -2.2688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6277   -3.0938    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
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  2  7  1  0  0  0  0
  7 24  1  0  0  0  0
  8  9  1  0  0  0  0
  8 12  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 10 14  1  6  0  0  0
 11 15  1  6  0  0  0
 10 16  1  1  0  0  0
 16 17  1  0  0  0  0
 26 13  1  0  0  0  0
 18 19  1  0  0  0  0
 18 23  1  0  0  0  0
 19 20  1  0  0  0  0
 19 26  1  1  0  0  0
 21 20  1  0  0  0  0
 20 27  1  6  0  0  0
 21 22  1  0  0  0  0
 21 28  1  1  0  0  0
 22 23  1  0  0  0  0
 22 25  1  6  0  0  0
 23 24  1  1  0  0  0
M  END


  Mrv0541 02241212592D          

 28 30  0  0  0  0            999 V2000
    1.9446   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2302   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2302   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9446   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6591   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6591   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5157   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2232   -0.8012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8906   -1.2862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6357   -2.0708    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.8107   -2.0708    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5557   -1.2862    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7711   -1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6357   -2.8958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8107   -2.8958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4505   -2.1998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9697   -1.5587    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6277   -0.6187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3422   -1.0312    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3422   -1.8563    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6277   -2.2688    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9132   -1.8563    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9132   -1.0312    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1988   -0.6187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1988   -2.2688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0566   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0566   -2.2688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6277   -3.0938    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
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  2  7  1  0  0  0  0
  7 24  1  0  0  0  0
  8  9  1  0  0  0  0
  8 12  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 10 14  1  6  0  0  0
 11 15  1  6  0  0  0
 10 16  1  1  0  0  0
 16 17  1  0  0  0  0
 26 13  1  0  0  0  0
 18 19  1  0  0  0  0
 18 23  1  0  0  0  0
 19 20  1  0  0  0  0
 19 26  1  1  0  0  0
 21 20  1  0  0  0  0
 20 27  1  6  0  0  0
 21 22  1  0  0  0  0
 21 28  1  1  0  0  0
 22 23  1  0  0  0  0
 22 25  1  6  0  0  0
 23 24  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0047146

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@@]1(O)CO[C@@H](OC[C@H]2O[C@@H](OCC3=CC=CC=C3)[C@H](O)[C@@H](O)[C@@H]2O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C18H26O10/c19-8-18(24)9-27-17(15(18)23)26-7-11-12(20)13(21)14(22)16(28-11)25-6-10-4-2-1-3-5-10/h1-5,11-17,19-24H,6-9H2/t11-,12-,13+,14-,15+,16-,17-,18-/m1/s1

> <INCHI_KEY>
NJMQSVWMCODQIP-FQXXIRCGSA-N

> <FORMULA>
C18H26O10

> <MOLECULAR_WEIGHT>
402.393

> <EXACT_MASS>
402.152597052

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_AVERAGE_POLARIZABILITY>
39.13811634066358

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R,4S,5S,6R)-2-(benzyloxy)-6-({[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)oxane-3,4,5-triol

> <ALOGPS_LOGP>
-1.52

> <JCHEM_LOGP>
-1.8414386570000003

> <ALOGPS_LOGS>
-1.34

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.318187680117607

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.7050003813713

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1423790163389214

> <JCHEM_POLAR_SURFACE_AREA>
158.3

> <JCHEM_REFRACTIVITY>
91.95739999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.86e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R,4S,5S,6R)-2-(benzyloxy)-6-({[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)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       3.630  -0.385   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.296  -1.155   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.296  -2.695   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.630  -3.465   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.964  -2.695   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.964  -1.155   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.963  -0.385   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -9.750  -1.496   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0     -10.996  -2.401   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -10.520  -3.865   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -8.980  -3.865   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -8.504  -2.401   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -7.039  -1.925   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0     -10.520  -5.405   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -8.980  -5.405   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0     -12.041  -4.106   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0     -13.010  -2.910   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -3.038  -1.155   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -4.372  -1.925   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.372  -3.465   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.038  -4.235   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.705  -3.465   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.705  -1.925   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -0.371  -1.155   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -0.371  -4.235   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -5.706  -1.155   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -5.706  -4.235   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -3.038  -5.775   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5                                                       
CONECT    7    2   24                                                       
CONECT    8    9   12                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   14   16                                             
CONECT   11   10   12   15                                                  
CONECT   12    8   11   13                                                  
CONECT   13   12   26                                                       
CONECT   14   10                                                            
CONECT   15   11                                                            
CONECT   16   10   17                                                       
CONECT   17   16                                                            
CONECT   18   19   23                                                       
CONECT   19   18   20   26                                                  
CONECT   20   19   21   27                                                  
CONECT   21   20   22   28                                                  
CONECT   22   21   23   25                                                  
CONECT   23   18   22   24                                                  
CONECT   24    7   23                                                       
CONECT   25   22                                                            
CONECT   26   13   19                                                       
CONECT   27   20                                                            
CONECT   28   21                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   60    0
END

View in JSmol

Synonyms

Value	Source
Benzyl 6-O-b-D-apiofuranosyl-b-D-glucoside	Generator
Benzyl 6-O-β-D-apiofuranosyl-β-D-glucoside	Generator

Chemical Formula

C₁₈H₂₆O₁₀

Average Mass

402.3930 Da

Monoisotopic Mass

402.15260 Da

IUPAC Name

(2R,3R,4S,5S,6R)-2-(benzyloxy)-6-({[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)oxane-3,4,5-triol

Traditional Name

(2R,3R,4S,5S,6R)-2-(benzyloxy)-6-({[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)oxane-3,4,5-triol

CAS Registry Number

Not Available

SMILES

OC[C@@]1(O)CO[C@@H](OC[C@H]2O[C@@H](OCC3=CC=CC=C3)[C@H](O)[C@@H](O)[C@@H]2O)[C@@H]1O

InChI Identifier

InChI=1S/C18H26O10/c19-8-18(24)9-27-17(15(18)23)26-7-11-12(20)13(21)14(22)16(28-11)25-6-10-4-2-1-3-5-10/h1-5,11-17,19-24H,6-9H2/t11-,12-,13+,14-,15+,16-,17-,18-/m1/s1

InChI Key

NJMQSVWMCODQIP-FQXXIRCGSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anethum graveolens	Plant	KNApSAcK
Atractylodes japonica	Plant	KNApSAcK
Atractylodes lancea	Plant	KNApSAcK
Betula maximowicziana	LOTUS Database	35616633
Bretschneidera sinensis	LOTUS Database	35616633
Breynia rostrata	LOTUS Database	35616633
Bupleurum falcatum	Plant	KNApSAcK
Camellia sinensis	LOTUS Database	35616633
Canthium berberidifolium	Plant	KNApSAcK
Chrysanthemum zawadskii	LOTUS Database	35616633
Coriandrum sativum L.	Plant	KNApSAcK
Crepidiastrum lanceolatum	LOTUS Database	35616633
Foeniculum vulgare	LOTUS Database	35616633
Glehnia littoralis	Plant	KNApSAcK
Glochidion rubrum	Plant	KNApSAcK
Grevillea robusta	Plant	KNApSAcK
Helichrysum arenarium	LOTUS Database	35616633
Holmskioldia sanguinea	LOTUS Database	35616633
Hydrangea macrophylla	LOTUS Database	35616633
Petroselinum crispum	LOTUS Database	35616633
Pimpinella anisum	Plant	KNApSAcK
Piper retrofractum	LOTUS Database	35616633
Pyrus bourgaeana	LOTUS Database	35616633
Salvia officinalis	LOTUS Database	35616633
Sambucus nigra	Plant	KNApSAcK
Schefflera rotundifolia	Plant	KNApSAcK
Vitis vinifera L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Youngia japonica	LOTUS Database	35616633
Zanthoxylum piperitum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

O-glycosyl compounds

Alternative Parents

Substituents

Disaccharide
O-glycosyl compound
Monocyclic benzene moiety
Oxane
Benzenoid
Tertiary alcohol
Tetrahydrofuran
Secondary alcohol
Polyol
Oxacycle
Acetal
Organoheterocyclic compound
Primary alcohol
Alcohol
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	-1.5	ALOGPS
logP	-1.8	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	11.71	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	158.3 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	91.96 m³·mol⁻¹	ChemAxon
Polarizability	39.14 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB007539

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

14079045

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Benzyl 6-O-beta-D-apiofuranosyl-beta-D-glucoside (NP0047146)

MOL for NP0047146 (Benzyl 6-O-beta-D-apiofuranosyl-beta-D-glucoside)

3D MOL for NP0047146 (Benzyl 6-O-beta-D-apiofuranosyl-beta-D-glucoside)

3D SDF for NP0047146 (Benzyl 6-O-beta-D-apiofuranosyl-beta-D-glucoside)

3D-SDF for NP0047146 (Benzyl 6-O-beta-D-apiofuranosyl-beta-D-glucoside)

PDB for NP0047146 (Benzyl 6-O-beta-D-apiofuranosyl-beta-D-glucoside)

3D PDB for NP0047146 (Benzyl 6-O-beta-D-apiofuranosyl-beta-D-glucoside)

SMILES for NP0047146 (Benzyl 6-O-beta-D-apiofuranosyl-beta-D-glucoside)

INCHI for NP0047146 (Benzyl 6-O-beta-D-apiofuranosyl-beta-D-glucoside)

Structure for NP0047146 (Benzyl 6-O-beta-D-apiofuranosyl-beta-D-glucoside)

3D Structure for NP0047146 (Benzyl 6-O-beta-D-apiofuranosyl-beta-D-glucoside)