NP-MRD: Showing NP-Card for 4-(β-d-glucopyranosyloxy) benzaldehyde (NP0331686)

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Record Information

Version

2.0

Created at

2023-06-21 04:01:46 UTC

Updated at

2024-09-03 04:16:31 UTC

NP-MRD ID

NP0331686

Natural Product DOI

https://doi.org/10.57994/0693

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-(β-d-glucopyranosyloxy) benzaldehyde

Description

26993-16-8, Also known as helicid, belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. Based on a literature review very few articles have been published on 26993-16-8.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 37  0  0  0  0  0  0  0  0999 V2000
    6.5243   -1.8394    1.4261 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3903   -2.3832    1.4154 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2280   -1.5641    1.0609 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3623   -0.2297    0.7451 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2635    0.5326    0.4131 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9754    0.0062    0.3782 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9194    0.8242    0.0378 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4209    0.5045   -0.0559 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9592    0.7246   -1.3299 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1547   -0.0013   -1.3750 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6440   -0.0434   -2.8057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6394   -0.6738   -3.5596 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1555    0.6920   -0.5173 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8707   -0.2974    0.1950 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5980    1.6464    0.4743 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6440    2.9393   -0.0978 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1912    1.3981    0.8889 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1877    0.8013    2.1526 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8404   -1.3252    0.6931 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9589   -2.0979    1.0303 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3331   -3.4117    1.6647 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3667    0.2041    0.7664 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3795    1.5824    0.1661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6336   -0.5553    0.1799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9521   -1.0033   -0.9921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7649    0.9680   -3.2143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5574   -0.6629   -2.8778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1661   -1.3465   -3.0055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9391    1.1793   -1.1679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8149    0.0011    0.3628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2645    1.7280    1.3829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5464    2.8984   -1.0862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6258    2.3592    1.0025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5288    1.3932    2.8613 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8745   -1.7887    0.6841 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8427   -3.1590    1.2802 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  2  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  2  1  2  0
  3 20  1  0
 20 19  2  0
  8 17  1  0
 17 18  1  0
 17 15  1  0
 15 16  1  0
 15 13  1  0
 13 14  1  0
 13 10  1  0
 19  6  1  0
 12 28  1  0
 11 26  1  0
 11 27  1  0
 10 25  1  1
  8 24  1  1
  5 23  1  0
  4 22  1  0
  2 21  1  0
 20 36  1  0
 19 35  1  0
 17 33  1  1
 18 34  1  0
 15 31  1  1
 16 32  1  0
 13 29  1  6
 14 30  1  0
M  END


  Mrv1652309092210142D          

 20 21  0  0  1  0            999 V2000
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
  8 17  1  0  0  0  0
 17 18  1  1  0  0  0
  6 19  1  0  0  0  0
 19 20  2  0  0  0  0
  3 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0331686

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](OC2=CC=C(C=O)C=C2)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C13H16O7/c14-5-7-1-3-8(4-2-7)19-13-12(18)11(17)10(16)9(6-15)20-13/h1-5,9-13,15-18H,6H2/t9-,10-,11+,12-,13-/m1/s1

> <INCHI_KEY>
OLZAGZCCJJBKNZ-UJPOAAIJSA-N

> <FORMULA>
C13H16O7

> <MOLECULAR_WEIGHT>
284.264

> <EXACT_MASS>
284.089602855

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
27.219089463027544

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzaldehyde

> <JCHEM_LOGP>
-0.8858852543333329

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.196091452653036

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.200141771940247

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092343686506

> <JCHEM_POLAR_SURFACE_AREA>
116.45000000000002

> <JCHEM_REFRACTIVITY>
66.7673

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.667 -12.320   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.334 -10.010   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   20                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   19                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   17                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15    8   18                                                  
CONECT   18   17                                                            
CONECT   19    6   20                                                       
CONECT   20   19    3                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol

Synonyms

Value	Source
Helicid	MeSH
Helicide	MeSH

Chemical Formula

C₁₃H₁₆O₇

Average Mass

284.2640 Da

Monoisotopic Mass

284.08960 Da

IUPAC Name

4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzaldehyde

Traditional Name

4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzaldehyde

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](OC2=CC=C(C=O)C=C2)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C13H16O7/c14-5-7-1-3-8(4-2-7)19-13-12(18)11(17)10(16)9(6-15)20-13/h1-5,9-13,15-18H,6H2/t9-,10-,11+,12-,13-/m1/s1

InChI Key

OLZAGZCCJJBKNZ-UJPOAAIJSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, CD3OD, experimental)	lihaibo1985124@sina.com	Not Available	Not Available	2023-06-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 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
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Phenolic glycosides

Alternative Parents

Substituents

Phenolic glycoside
Hexose monosaccharide
O-glycosyl compound
Phenoxy compound
Benzaldehyde
Benzoyl
Phenol ether
Aryl-aldehyde
Monocyclic benzene moiety
Monosaccharide
Oxane
Benzenoid
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Acetal
Polyol
Aldehyde
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	-0.89	ChemAxon
pKa (Strongest Acidic)	12.2	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	116.45 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	66.77 m³·mol⁻¹	ChemAxon
Polarizability	27.22 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

5890598

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

7573800

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

DOI: 10.1080/14786419.2023.2216348

Showing NP-Card for 4-(β-d-glucopyranosyloxy) benzaldehyde (NP0331686)

MOL for NP0331686 (4-(β-d-glucopyranosyloxy) benzaldehyde)

3D MOL for NP0331686 (4-(β-d-glucopyranosyloxy) benzaldehyde)

3D SDF for NP0331686 (4-(β-d-glucopyranosyloxy) benzaldehyde)

3D-SDF for NP0331686 (4-(β-d-glucopyranosyloxy) benzaldehyde)

PDB for NP0331686 (4-(β-d-glucopyranosyloxy) benzaldehyde)

3D PDB for NP0331686 (4-(β-d-glucopyranosyloxy) benzaldehyde)

SMILES for NP0331686 (4-(β-d-glucopyranosyloxy) benzaldehyde)

INCHI for NP0331686 (4-(β-d-glucopyranosyloxy) benzaldehyde)

Structure for NP0331686 (4-(β-d-glucopyranosyloxy) benzaldehyde)

3D Structure for NP0331686 (4-(β-d-glucopyranosyloxy) benzaldehyde)