NP-MRD: Showing NP-Card for alpha-Hydrojuglone 4-O-b-D-glucoside (NP0047908)

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Record Information

Version

2.0

Created at

2022-03-17 20:47:55 UTC

Updated at

2022-03-17 20:47:55 UTC

NP-MRD ID

NP0047908

Secondary Accession Numbers

None

Natural Product Identification

Common Name

alpha-Hydrojuglone 4-O-b-D-glucoside

Description

Alpha-Hydrojuglone 4-O-b-D-glucoside 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. Alpha-Hydrojuglone 4-O-b-D-glucoside is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, alpha-Hydrojuglone 4-O-b-D-glucoside has been detected, but not quantified in, a few different foods, such as black walnuts, common walnuts, and nuts. alpha-Hydrojuglone 4-O-b-D-glucoside is found in Juglans mandshurica and Plumbago europaea. This could make alpha-hydrojuglone 4-O-b-D-glucoside a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061307402D          

 24 26  0  0  0  0            999 V2000
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    5.7750    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    0.8250    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    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    4.9500    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
    5.0013    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  5  4  2  0  0  0  0
  7  2  1  0  0  0  0
  8  4  1  0  0  0  0
  8  7  2  0  0  0  0
  9  3  2  0  0  0  0
 10  5  1  0  0  0  0
 11  6  1  0  0  0  0
 12  7  1  0  0  0  0
 12  9  1  0  0  0  0
 12 10  2  0  0  0  0
 13 11  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17  6  1  0  0  0  0
 18  8  1  0  0  0  0
 19  9  1  0  0  0  0
 20 13  1  0  0  0  0
 21 14  1  0  0  0  0
 22 15  1  0  0  0  0
 23 10  1  0  0  0  0
 23 16  1  0  0  0  0
 24 11  1  0  0  0  0
 24 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047908

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC(OC2=C3C(O)=CC=CC3=C(O)C=C2)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C16H18O8/c17-6-11-13(20)14(21)15(22)16(24-11)23-10-5-4-8(18)7-2-1-3-9(19)12(7)10/h1-5,11,13-22H,6H2

> <INCHI_KEY>
LASMTIIWUCJLEH-UHFFFAOYSA-N

> <FORMULA>
C16H18O8

> <MOLECULAR_WEIGHT>
338.3093

> <EXACT_MASS>
338.100167552

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
32.39360978980181

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(4,8-dihydroxynaphthalen-1-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

> <ALOGPS_LOGP>
-0.53

> <JCHEM_LOGP>
-0.2160414856666668

> <ALOGPS_LOGS>
-1.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.67534108508516

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.895603443978237

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810923462286993

> <JCHEM_POLAR_SURFACE_AREA>
139.84

> <JCHEM_REFRACTIVITY>
80.59530000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.89e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(4,8-dihydroxynaphthalen-1-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

> <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   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002  10.780   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002   9.240   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.336   8.470   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       9.336  11.550   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      10.669   9.240   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      10.669   6.160   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       8.002   4.620   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       6.668   8.470   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    7                                                       
CONECT    3    1    9                                                       
CONECT    4    5    8                                                       
CONECT    5    4   10                                                       
CONECT    6   11   17                                                       
CONECT    7    2    8   12                                                  
CONECT    8    4    7   18                                                  
CONECT    9    3   12   19                                                  
CONECT   10    5   12   23                                                  
CONECT   11    6   13   24                                                  
CONECT   12    7    9   10                                                  
CONECT   13   11   14   20                                                  
CONECT   14   13   15   21                                                  
CONECT   15   14   16   22                                                  
CONECT   16   15   23   24                                                  
CONECT   17    6                                                            
CONECT   18    8                                                            
CONECT   19    9                                                            
CONECT   20   13                                                            
CONECT   21   14                                                            
CONECT   22   15                                                            
CONECT   23   10   16                                                       
CONECT   24   11   16                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Value	Source
a-Hydrojuglone 4-O-b-D-glucoside	Generator
Α-hydrojuglone 4-O-b-D-glucoside	Generator
alpha-Hydrojuglone-4-glucoside	HMDB

Chemical Formula

C₁₆H₁₈O₈

Average Mass

338.3093 Da

Monoisotopic Mass

338.10017 Da

IUPAC Name

2-[(4,8-dihydroxynaphthalen-1-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Traditional Name

2-[(4,8-dihydroxynaphthalen-1-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

CAS Registry Number

39015-63-9

SMILES

OCC1OC(OC2=C3C(O)=CC=CC3=C(O)C=C2)C(O)C(O)C1O

InChI Identifier

InChI=1S/C16H18O8/c17-6-11-13(20)14(21)15(22)16(24-11)23-10-5-4-8(18)7-2-1-3-9(19)12(7)10/h1-5,11,13-22H,6H2

InChI Key

LASMTIIWUCJLEH-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Juglans mandshurica	Plant	KNApSAcK
Juglans nigra L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Juglans regia	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Plumbago europaea	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
Hexose monosaccharide
1-naphthol
O-glycosyl compound
Naphthalene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Monosaccharide
Benzenoid
Oxane
Secondary alcohol
Acetal
Oxacycle
Organoheterocyclic compound
Polyol
Alcohol
Primary alcohol
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	-0.53	ALOGPS
logP	-0.22	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	8.9	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	139.84 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	80.6 m³·mol⁻¹	ChemAxon
Polarizability	32.39 Å³	ChemAxon
Number of Rings	3	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

HMDB0034242

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB012555

KNApSAcK ID

C00029670

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

78190001

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for alpha-Hydrojuglone 4-O-b-D-glucoside (NP0047908)

MOL for NP0047908 (alpha-Hydrojuglone 4-O-b-D-glucoside)

3D MOL for NP0047908 (alpha-Hydrojuglone 4-O-b-D-glucoside)

3D SDF for NP0047908 (alpha-Hydrojuglone 4-O-b-D-glucoside)

3D-SDF for NP0047908 (alpha-Hydrojuglone 4-O-b-D-glucoside)

PDB for NP0047908 (alpha-Hydrojuglone 4-O-b-D-glucoside)

3D PDB for NP0047908 (alpha-Hydrojuglone 4-O-b-D-glucoside)

SMILES for NP0047908 (alpha-Hydrojuglone 4-O-b-D-glucoside)

INCHI for NP0047908 (alpha-Hydrojuglone 4-O-b-D-glucoside)

Structure for NP0047908 (alpha-Hydrojuglone 4-O-b-D-glucoside)

3D Structure for NP0047908 (alpha-Hydrojuglone 4-O-b-D-glucoside)