NP-MRD: Showing NP-Card for 1,2-di-(4-hydroxybenzoyl)-β-glucopyranose (NP0333164)

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Record Information

Version

1.0

Created at

2024-05-11 22:27:12 UTC

Updated at

2024-05-11 22:31:52 UTC

NP-MRD ID

NP0333164

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1,2-di-(4-hydroxybenzoyl)-β-glucopyranose

Description

Not Available

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01242301032D          

 33 33  0  0  1  0            999 V2000
   -0.3742    3.0839    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3742    2.2589    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3402    1.8464    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0547    2.2589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7692    1.8464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3402    1.0214    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3742    0.6089    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3742   -0.2161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3402   -0.6286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3402   -1.4536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0547   -1.8661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0547   -2.6911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3402   -3.1036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3402   -3.9286    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3742   -2.6911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3742   -1.8661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0547   -0.2161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0887    1.0214    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8032    0.6089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0887    1.8464    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8032    2.2589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9513    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1263    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.5786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -5.9911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -6.8161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -7.2286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -8.0536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -7.2286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -8.0536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -8.4661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -9.2911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.5786    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  4  5  1  0  0  0  0
  3  6  1  0  0  0  0
  7  6  1  0  0  0  0
  7  8  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 10 16  1  0  0  0  0
  9 17  2  0  0  0  0
 18  7  1  0  0  0  0
 18 19  1  6  0  0  0
  2 20  1  0  0  0  0
 20 18  1  0  0  0  0
 20 21  1  1  0  0  0
 22 23  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 26 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 28 31  1  0  0  0  0
 31 32  1  0  0  0  0
 25 33  2  0  0  0  0
M  RAD  1  19   2
M  END


  Mrv2104 01242301032D          

 33 33  0  0  1  0            999 V2000
   -0.3742    3.0839    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3742    2.2589    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3402    1.8464    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0547    2.2589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7692    1.8464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3402    1.0214    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3742    0.6089    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3742   -0.2161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3402   -0.6286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3402   -1.4536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0547   -1.8661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0547   -2.6911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3402   -3.1036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3402   -3.9286    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3742   -2.6911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3742   -1.8661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0547   -0.2161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0887    1.0214    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8032    0.6089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0887    1.8464    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8032    2.2589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9513    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1263    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.5786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -5.9911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -6.8161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -7.2286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -8.0536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -7.2286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -8.0536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -8.4661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -9.2911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.5786    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  4  5  1  0  0  0  0
  3  6  1  0  0  0  0
  7  6  1  0  0  0  0
  7  8  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 10 16  1  0  0  0  0
  9 17  2  0  0  0  0
 18  7  1  0  0  0  0
 18 19  1  6  0  0  0
  2 20  1  0  0  0  0
 20 18  1  0  0  0  0
 20 21  1  1  0  0  0
 22 23  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 26 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 28 31  1  0  0  0  0
 31 32  1  0  0  0  0
 25 33  2  0  0  0  0
M  RAD  1  19   2
M  END
> <DATABASE_ID>
NP0333164

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC.CC(=O)C1=CC=C(O)C=C1.[O][C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC(=O)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C13H15O8.C8H8O2.C2H6/c14-5-8-9(16)10(17)11(18)13(20-8)21-12(19)6-1-3-7(15)4-2-6;1-6(9)7-2-4-8(10)5-3-7;1-2/h1-4,8-11,13-17H,5H2;2-5,10H,1H3;1-2H3/t8-,9-,10+,11-,13+;;/m1../s1

> <INCHI_KEY>
TYLDLWWAQIJBMA-ZVNZFUDFSA-N

> <FORMULA>
C23H29O10

> <MOLECULAR_WEIGHT>
465.475

> <EXACT_MASS>
465.176072134

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
27.94929897825428

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-(4-hydroxyphenyl)ethan-1-one; [(2S,3R,4R,5S,6R)-4,5-dihydroxy-2-(4-hydroxybenzoyloxy)-6-(hydroxymethyl)oxan-3-yl]oxidanyl; ethane

> <JCHEM_LOGP>
-0.2994

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.731846949023424

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.469498235985256

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981069460985019

> <JCHEM_POLAR_SURFACE_AREA>
116.45

> <JCHEM_REFRACTIVITY>
78.27660000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4R,5S,6R)-4,5-dihydroxy-2-(4-hydroxybenzoyloxy)-6-(hydroxymethyl)oxan-3-yloxidanyl; ethane; hydroxyacetophenone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-JAN-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JAN-23         0                                  
HETATM    1  O   UNK     0      -0.699   5.757   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -0.699   4.217   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.635   3.447   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.969   4.217   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       3.302   3.447   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       0.635   1.907   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -0.699   1.137   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.699  -0.403   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.635  -1.173   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.635  -2.713   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.969  -3.483   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.969  -5.023   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.635  -5.793   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.635  -7.333   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -0.699  -5.023   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.699  -3.483   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.969  -0.403   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -2.032   1.907   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -3.366   1.137   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -2.032   3.447   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -3.366   4.217   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       9.242   0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.702   0.000   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.334 -10.413   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.000 -11.183   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.000 -12.723   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.334 -13.493   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.334 -15.033   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.334 -13.493   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -1.334 -15.033   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.000 -15.803   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -0.000 -17.343   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       1.334 -10.413   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   20                                                  
CONECT    3    2    4    6                                                  
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    3    7                                                       
CONECT    7    6    8   18                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   17                                                  
CONECT   10    9   11   16                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   10                                                       
CONECT   17    9                                                            
CONECT   18    7   19   20                                                  
CONECT   19   18                                                            
CONECT   20    2   18   21                                                  
CONECT   21   20                                                            
CONECT   22   23                                                            
CONECT   23   22                                                            
CONECT   24   25                                                            
CONECT   25   24   26   33                                                  
CONECT   26   25   27   29                                                  
CONECT   27   26   28                                                       
CONECT   28   27   31                                                       
CONECT   29   26   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   28   32                                                  
CONECT   32   31                                                            
CONECT   33   25                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₂₉O₁₀

Average Mass

465.4750 Da

Monoisotopic Mass

465.17607 Da

IUPAC Name

1-(4-hydroxyphenyl)ethan-1-one; [(2S,3R,4R,5S,6R)-4,5-dihydroxy-2-(4-hydroxybenzoyloxy)-6-(hydroxymethyl)oxan-3-yl]oxidanyl; ethane

Traditional Name

(2S,3R,4R,5S,6R)-4,5-dihydroxy-2-(4-hydroxybenzoyloxy)-6-(hydroxymethyl)oxan-3-yloxidanyl; ethane; hydroxyacetophenone

CAS Registry Number

Not Available

SMILES

CC.CC(=O)C1=CC=C(O)C=C1.[O][C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC(=O)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C13H15O8.C8H8O2.C2H6/c14-5-8-9(16)10(17)11(18)13(20-8)21-12(19)6-1-3-7(15)4-2-6;1-6(9)7-2-4-8(10)5-3-7;1-2/h1-4,8-11,13-17H,5H2;2-5,10H,1H3;1-2H3/t8-,9-,10+,11-,13+;;/m1../s1

InChI Key

TYLDLWWAQIJBMA-ZVNZFUDFSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	huohuixia1989@163.com	Not Available	Not Available	2024-05-11	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD3OD, experimental)	huohuixia1989@163.com	Not Available	Not Available	2024-05-11	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, CD3OD, experimental)	huohuixia1989@163.com	Not Available	Not Available	2024-05-11	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	huohuixia1989@163.com	Not Available	Not Available	2024-05-11	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, simulated)	Not Available	Not Available	Not Available	2024-05-11	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
negundo var. cannabifolia		Not Available

Chemical Taxonomy

Classification

Not classified

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	-0.3	ChemAxon
pKa (Strongest Acidic)	8.47	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	5	ChemAxon
Refractivity	78.28 m³·mol⁻¹	ChemAxon
Polarizability	27.95 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

Not Available

References

General References

Sun J, Li M, Wang Y, Chang C, Pei Y, Zeng K, Zhao Y, Zheng J, Song Y, Tu P, Huo H, Li J: Phenolic Glucosides from the Leaves of Vitex negundo var. cannabifolia. Chem Biodivers. 2022 Nov;19(11):e202200652. doi: 10.1002/cbdv.202200652. Epub 2022 Oct 10. [PubMed:36129755 ]

Showing NP-Card for 1,2-di-(4-hydroxybenzoyl)-β-glucopyranose (NP0333164)

MOL for NP0333164 (1,2-di-(4-hydroxybenzoyl)-β-glucopyranose)

3D MOL for NP0333164 (1,2-di-(4-hydroxybenzoyl)-β-glucopyranose)

3D SDF for NP0333164 (1,2-di-(4-hydroxybenzoyl)-β-glucopyranose)

3D-SDF for NP0333164 (1,2-di-(4-hydroxybenzoyl)-β-glucopyranose)

PDB for NP0333164 (1,2-di-(4-hydroxybenzoyl)-β-glucopyranose)

3D PDB for NP0333164 (1,2-di-(4-hydroxybenzoyl)-β-glucopyranose)

SMILES for NP0333164 (1,2-di-(4-hydroxybenzoyl)-β-glucopyranose)

INCHI for NP0333164 (1,2-di-(4-hydroxybenzoyl)-β-glucopyranose)

Structure for NP0333164 (1,2-di-(4-hydroxybenzoyl)-β-glucopyranose)

3D Structure for NP0333164 (1,2-di-(4-hydroxybenzoyl)-β-glucopyranose)