NP-MRD: Showing NP-Card for 6-O-Acetylarbutin (NP0047838)

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Record Information

Version

2.0

Created at

2022-03-17 20:46:47 UTC

Updated at

2022-03-17 20:46:47 UTC

NP-MRD ID

NP0047838

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-O-Acetylarbutin

Description

6-O-Acetylarbutin, also known as pyroside, 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. 6-O-Acetylarbutin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 6-O-Acetylarbutin has been detected, but not quantified in, several different foods, such as cereals and cereal products, fruits, pears, and pomes. 6-O-Acetylarbutin is found in Halocarpus biformis, Vaccinium dunalianum, Vaccinium vitis-idaea and Viburnum wrightii. This could make 6-O-acetylarbutin a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061307322D          

 22 23  0  0  0  0            999 V2000
   -0.7145    8.6625    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
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  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
    0.0000    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 O   0  0  0  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
    0.0000    7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  7  1  1  0  0  0  0
  8  2  2  0  0  0  0
  8  3  1  0  0  0  0
  9  4  2  0  0  0  0
  9  5  1  0  0  0  0
 10  6  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15  7  2  0  0  0  0
 16  8  1  0  0  0  0
 17 11  1  0  0  0  0
 18 12  1  0  0  0  0
 19 13  1  0  0  0  0
 20  6  1  0  0  0  0
 20  7  1  0  0  0  0
 21  9  1  0  0  0  0
 21 14  1  0  0  0  0
 22 10  1  0  0  0  0
 22 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047838

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OCC1OC(OC2=CC=C(O)C=C2)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C14H18O8/c1-7(15)20-6-10-11(17)12(18)13(19)14(22-10)21-9-4-2-8(16)3-5-9/h2-5,10-14,16-19H,6H2,1H3

> <INCHI_KEY>
XABUTYXAHYMCDK-UHFFFAOYSA-N

> <FORMULA>
C14H18O8

> <MOLECULAR_WEIGHT>
314.2879

> <EXACT_MASS>
314.100167552

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
30.13565670737707

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[3,4,5-trihydroxy-6-(4-hydroxyphenoxy)oxan-2-yl]methyl acetate

> <ALOGPS_LOGP>
-0.59

> <JCHEM_LOGP>
-0.460827510333333

> <ALOGPS_LOGS>
-1.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.20334058383637

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.820462402278373

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6491028148207487

> <JCHEM_POLAR_SURFACE_AREA>
125.68000000000002

> <JCHEM_REFRACTIVITY>
71.3157

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.27e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[3,4,5-trihydroxy-6-(4-hydroxyphenoxy)oxan-2-yl]methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -1.334  16.170   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  13.090   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  15.400   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  11.550   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000  10.780   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334   8.470   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   9.240   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.334  16.170   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -1.334  11.550   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -1.334   8.470   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       0.000  13.860   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       4.001   8.470   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       2.667  10.780   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2    4    8                                                       
CONECT    3    5    8                                                       
CONECT    4    2    9                                                       
CONECT    5    3    9                                                       
CONECT    6   10   20                                                       
CONECT    7    1   15   20                                                  
CONECT    8    2    3   16                                                  
CONECT    9    4    5   21                                                  
CONECT   10    6   11   22                                                  
CONECT   11   10   12   17                                                  
CONECT   12   11   13   18                                                  
CONECT   13   12   14   19                                                  
CONECT   14   13   21   22                                                  
CONECT   15    7                                                            
CONECT   16    8                                                            
CONECT   17   11                                                            
CONECT   18   12                                                            
CONECT   19   13                                                            
CONECT   20    6    7                                                       
CONECT   21    9   14                                                       
CONECT   22   10   14                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

View in JSmol

Synonyms

Value	Source
Pyroside	HMDB
[3,4,5-Trihydroxy-6-(4-hydroxyphenoxy)oxan-2-yl]methyl acetic acid	Generator

Chemical Formula

C₁₄H₁₈O₈

Average Mass

314.2879 Da

Monoisotopic Mass

314.10017 Da

IUPAC Name

[3,4,5-trihydroxy-6-(4-hydroxyphenoxy)oxan-2-yl]methyl acetate

Traditional Name

[3,4,5-trihydroxy-6-(4-hydroxyphenoxy)oxan-2-yl]methyl acetate

CAS Registry Number

10338-88-2

SMILES

CC(=O)OCC1OC(OC2=CC=C(O)C=C2)C(O)C(O)C1O

InChI Identifier

InChI=1S/C14H18O8/c1-7(15)20-6-10-11(17)12(18)13(19)14(22-10)21-9-4-2-8(16)3-5-9/h2-5,10-14,16-19H,6H2,1H3

InChI Key

XABUTYXAHYMCDK-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Halocarpus biformis	LOTUS Database	35616633
Pyrus communis	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Vaccinium dunalianum	LOTUS Database	35616633
Vaccinium vitis-idaea	Plant	KNApSAcK
Viburnum wrightii	LOTUS Database	35616633

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
O-glycosyl compound
4-alkoxyphenol
Phenoxy compound
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Monosaccharide
Oxane
Benzenoid
Carboxylic acid ester
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Monocarboxylic acid or derivatives
Acetal
Carboxylic acid derivative
Polyol
Hydrocarbon derivative
Carbonyl group
Organic oxide
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	-0.59	ALOGPS
logP	-0.46	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	9.82	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	125.68 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	71.32 m³·mol⁻¹	ChemAxon
Polarizability	30.14 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

HMDB0034060

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB012309

KNApSAcK ID

Not Available

Chemspider ID

13277076

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14542705

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 6-O-Acetylarbutin (NP0047838)

MOL for NP0047838 (6-O-Acetylarbutin)

3D MOL for NP0047838 (6-O-Acetylarbutin)

3D SDF for NP0047838 (6-O-Acetylarbutin)

3D-SDF for NP0047838 (6-O-Acetylarbutin)

PDB for NP0047838 (6-O-Acetylarbutin)

3D PDB for NP0047838 (6-O-Acetylarbutin)

SMILES for NP0047838 (6-O-Acetylarbutin)

INCHI for NP0047838 (6-O-Acetylarbutin)

Structure for NP0047838 (6-O-Acetylarbutin)

3D Structure for NP0047838 (6-O-Acetylarbutin)