NP-MRD: Showing NP-Card for 1-O-β-d-glucopyranosyl benzoate (NP0331688)

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Record Information

Version

2.0

Created at

2023-06-21 04:04:27 UTC

Updated at

2024-09-03 04:16:31 UTC

NP-MRD ID

NP0331688

Natural Product DOI

https://doi.org/10.57994/0695

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-O-β-d-glucopyranosyl benzoate

Description

Benzoyl-beta-D-glucoside belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity. Benzoyl-beta-D-glucoside is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309272006422D          

 20 21  0  0  0  0            999 V2000
 9999.9951 9999.1763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2799 9999.5876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.279910000.4123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.421710001.6492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.137110002.0615    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.4217 9998.3517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.8524 9999.1763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.852410000.8246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5668 9999.1762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8524 9999.5887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1378 9999.1761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1378 9998.3512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8523 9997.9387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5668 9998.3512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.423710000.8252    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.709210000.4127    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.7092 9999.5876    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.4237 9999.1752    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10002.1382 9999.5876    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10002.138210000.4127    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  4  5  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14  9  1  0  0  0  0
  2  9  1  0  0  0  0
 15 20  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17  1  1  6  0  0  0
 15  4  1  6  0  0  0
 20  8  1  1  0  0  0
 19  7  1  6  0  0  0
 18  6  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0331688

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](OC(=O)C2=CC=CC=C2)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C13H16O7/c14-6-8-9(15)10(16)11(17)13(19-8)20-12(18)7-4-2-1-3-5-7/h1-5,8-11,13-17H,6H2/t8-,9-,10+,11-,13+/m1/s1

> <INCHI_KEY>
LVFCLUMIBMHAFL-HMUNZLOLSA-N

> <FORMULA>
C13H16O7

> <MOLECULAR_WEIGHT>
284.264

> <EXACT_MASS>
284.089602855

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
26.769876424206963

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl benzoate

> <ALOGPS_LOGP>
-0.74

> <JCHEM_LOGP>
-0.4372393693333334

> <ALOGPS_LOGS>
-1.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.194434629099312

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.195711498286794

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981093823879755

> <JCHEM_POLAR_SURFACE_AREA>
116.45000000000002

> <JCHEM_REFRACTIVITY>
65.74540000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.63e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
benzoyl-β-D-glucoside

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  O   UNK     0    8666.6588665.129   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0    8665.3228665.897   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8665.3228667.436   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0    8669.3218669.745   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0    8670.6568670.515   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8669.3218663.590   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0    8671.9918665.129   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    8671.9918668.206   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0    8663.9918665.129   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8662.6588665.899   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8661.3248665.129   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8661.3248663.589   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8662.6588662.819   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8663.9918663.589   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8669.3248668.207   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0    8667.9918667.437   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0    8667.9918665.897   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8669.3248665.127   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8670.6588665.897   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8670.6588667.437   0.000  0.00  0.00           C+0
CONECT    1    2   17                                                       
CONECT    2    1    3    9                                                  
CONECT    3    2                                                            
CONECT    4    5   15                                                       
CONECT    5    4                                                            
CONECT    6   18                                                            
CONECT    7   19                                                            
CONECT    8   20                                                            
CONECT    9   10   14    2                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    9                                                       
CONECT   15   20   16    4                                                  
CONECT   16   15   17                                                       
CONECT   17   18   16    1                                                  
CONECT   18   17   19    6                                                  
CONECT   19   18   20    7                                                  
CONECT   20   15   19    8                                                  
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol

Synonyms

Value	Source
Benzoyl-b-D-glucoside	Generator
Benzoyl-β-D-glucoside	Generator
1-O-Benzoyl-beta-D-glucopyranoside	PhytoBank
Periplanetin	PhytoBank
Benzoic acid 1-O-beta-D-glucopyranosyl ester	PhytoBank
Benzoic acid 1-O-β-D-glucopyranosyl ester	PhytoBank
Benzoyl beta-D-glucoside	PhytoBank
Benzoyl β-D-glucoside	PhytoBank
Benzoyl-beta-glucoside	PhytoBank
Benzoyl-β-glucoside	PhytoBank
beta-D-Glucopyranosyl benzoate	PhytoBank
β-D-Glucopyranosyl benzoate	PhytoBank

Chemical Formula

C₁₃H₁₆O₇

Average Mass

284.2640 Da

Monoisotopic Mass

284.08960 Da

IUPAC Name

(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl benzoate

Traditional Name

benzoyl-β-D-glucoside

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](OC(=O)C2=CC=CC=C2)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C13H16O7/c14-6-8-9(15)10(16)11(17)13(19-8)20-12(18)7-4-2-1-3-5-7/h1-5,8-11,13-17H,6H2/t8-,9-,10+,11-,13+/m1/s1

InChI Key

LVFCLUMIBMHAFL-HMUNZLOLSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, CD3OD, experimental)	lihaibo1985124@sina.com	Not Available	Not Available	2023-06-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD3OD, experimental)	lihaibo1985124@sina.com	Not Available	Not Available	2023-06-21	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Hexoses

Alternative Parents

Substituents

Hexose monosaccharide
Benzoate ester
Benzoic acid or derivatives
Benzoyl
Monocyclic benzene moiety
Oxane
Benzenoid
Carboxylic acid ester
Secondary alcohol
Polyol
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Carboxylic acid derivative
Oxacycle
Acetal
Alcohol
Hydrocarbon derivative
Organic oxide
Primary alcohol
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	-0.74	ALOGPS
logP	-0.44	ChemAxon
logS	-1	ALOGPS
pKa (Strongest Acidic)	12.2	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	116.45 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	65.75 m³·mol⁻¹	ChemAxon
Polarizability	26.77 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

18620219

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Benzoyl-beta-D-glucoside

METLIN ID

Not Available

PubChem Compound

12314096

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 1-O-β-d-glucopyranosyl benzoate (NP0331688)

MOL for NP0331688 (1-O-β-d-glucopyranosyl benzoate)

3D MOL for NP0331688 (1-O-β-d-glucopyranosyl benzoate)

3D SDF for NP0331688 (1-O-β-d-glucopyranosyl benzoate)

3D-SDF for NP0331688 (1-O-β-d-glucopyranosyl benzoate)

PDB for NP0331688 (1-O-β-d-glucopyranosyl benzoate)

3D PDB for NP0331688 (1-O-β-d-glucopyranosyl benzoate)

SMILES for NP0331688 (1-O-β-d-glucopyranosyl benzoate)

INCHI for NP0331688 (1-O-β-d-glucopyranosyl benzoate)

Structure for NP0331688 (1-O-β-d-glucopyranosyl benzoate)

3D Structure for NP0331688 (1-O-β-d-glucopyranosyl benzoate)