NP-MRD: Showing NP-Card for 4,5-dihydroxy-6-[2-(hydroxymethyl)phenoxy]-2-[(3,4,5-trihydroxybenzoyloxy)methyl]oxan-3-yl 3,4,5-trihydroxybenzoate (NP0325433)

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Record Information

Version

2.0

Created at

2022-09-12 06:11:24 UTC

Updated at

2022-09-12 06:11:25 UTC

NP-MRD ID

NP0325433

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4,5-dihydroxy-6-[2-(hydroxymethyl)phenoxy]-2-[(3,4,5-trihydroxybenzoyloxy)methyl]oxan-3-yl 3,4,5-trihydroxybenzoate

Description

{4,5-Dihydroxy-6-[2-(hydroxymethyl)phenoxy]-3-(3,4,5-trihydroxybenzoyloxy)oxan-2-yl}methyl 3,4,5-trihydroxybenzoate belongs to the class of organic compounds known as hemiacetals. Hemiacetals are compounds comprising the hemiacetal functional group, with the general formula R2C(OH)OR' ( R' not Hydrogen ). 4,5-dihydroxy-6-[2-(hydroxymethyl)phenoxy]-2-[(3,4,5-trihydroxybenzoyloxy)methyl]oxan-3-yl 3,4,5-trihydroxybenzoate is found in Alangium chinense. {4,5-Dihydroxy-6-[2-(hydroxymethyl)phenoxy]-3-(3,4,5-trihydroxybenzoyloxy)oxan-2-yl}methyl 3,4,5-trihydroxybenzoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161522282D          

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M  END

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M  END


  Mrv1533004161522282D          

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   -6.4302   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -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
  1  2  1  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
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 17 25  1  0  0  0  0
 12 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  2  0  0  0  0
 30 38  1  0  0  0  0
 26 39  1  0  0  0  0
 39 40  1  0  0  0  0
 39 41  1  0  0  0  0
 10 41  1  0  0  0  0
 41 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0325433

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1=CC=CC=C1OC1OC(COC(=O)C2=CC(O)=C(O)C(O)=C2)C(OC(=O)C2=CC(O)=C(O)C(O)=C2)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C27H26O15/c28-9-11-3-1-2-4-18(11)40-27-23(36)22(35)24(42-26(38)13-7-16(31)21(34)17(32)8-13)19(41-27)10-39-25(37)12-5-14(29)20(33)15(30)6-12/h1-8,19,22-24,27-36H,9-10H2

> <INCHI_KEY>
HOXVUKKGXNVMRX-UHFFFAOYSA-N

> <FORMULA>
C27H26O15

> <MOLECULAR_WEIGHT>
590.49

> <EXACT_MASS>
590.127170137

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
55.27831322458358

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{4,5-dihydroxy-6-[2-(hydroxymethyl)phenoxy]-3-(3,4,5-trihydroxybenzoyloxy)oxan-2-yl}methyl 3,4,5-trihydroxybenzoate

> <ALOGPS_LOGP>
1.69

> <JCHEM_LOGP>
1.8034704009999993

> <ALOGPS_LOGS>
-2.94

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.405962340274622

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.804492642095915

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6940315877676957

> <JCHEM_POLAR_SURFACE_AREA>
253.12999999999997

> <JCHEM_REFRACTIVITY>
138.5286

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.74e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{4,5-dihydroxy-6-[2-(hydroxymethyl)phenoxy]-3-(3,4,5-trihydroxybenzoyloxy)oxan-2-yl}methyl 3,4,5-trihydroxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -0.000  -7.700   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.000  -9.240   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000 -12.320   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334 -11.550   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334 -10.010   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      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -8.002  -7.700   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0     -10.669  -7.700   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0     -10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0     -10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0     -12.003  -2.310   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -6.668 -11.550   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -8.002 -12.320   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -8.002 -13.860   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -6.668 -14.630   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -9.336 -14.630   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -9.336 -16.170   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0     -10.669 -16.940   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0     -10.669 -18.480   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0     -12.003 -16.170   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0     -13.337 -16.940   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0     -12.003 -14.630   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0     -13.337 -13.860   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0     -10.669 -13.860   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -5.335 -13.860   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      -4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      -2.667 -12.320   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   41                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   26                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   25                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   17                                                       
CONECT   26   12   27   39                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   38                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   30                                                       
CONECT   39   26   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   10   42                                                  
CONECT   42   41                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   90    0
END

View in JSmol

Synonyms

Value	Source
{4,5-dihydroxy-6-[2-(hydroxymethyl)phenoxy]-3-(3,4,5-trihydroxybenzoyloxy)oxan-2-yl}methyl 3,4,5-trihydroxybenzoic acid	Generator

Chemical Formula

C₂₇H₂₆O₁₅

Average Mass

590.4900 Da

Monoisotopic Mass

590.12717 Da

IUPAC Name

{4,5-dihydroxy-6-[2-(hydroxymethyl)phenoxy]-3-(3,4,5-trihydroxybenzoyloxy)oxan-2-yl}methyl 3,4,5-trihydroxybenzoate

Traditional Name

{4,5-dihydroxy-6-[2-(hydroxymethyl)phenoxy]-3-(3,4,5-trihydroxybenzoyloxy)oxan-2-yl}methyl 3,4,5-trihydroxybenzoate

CAS Registry Number

Not Available

SMILES

OCC1=CC=CC=C1OC1OC(COC(=O)C2=CC(O)=C(O)C(O)=C2)C(OC(=O)C2=CC(O)=C(O)C(O)=C2)C(O)C1O

InChI Identifier

InChI=1S/C27H26O15/c28-9-11-3-1-2-4-18(11)40-27-23(36)22(35)24(42-26(38)13-7-16(31)21(34)17(32)8-13)19(41-27)10-39-25(37)12-5-14(29)20(33)15(30)6-12/h1-8,19,22-24,27-36H,9-10H2

InChI Key

HOXVUKKGXNVMRX-UHFFFAOYSA-N

Experimental Spectra

Not Available

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

Species Name	Source	Reference
Alangium chinense	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hemiacetals. Hemiacetals are compounds comprising the hemiacetal functional group, with the general formula R2C(OH)OR' ( R' not Hydrogen ).

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Ethers

Direct Parent

Hemiacetals

Alternative Parents

Substituents

Hemiacetal
Hydrocarbon derivative
Primary alcohol
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic 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	1.69	ALOGPS
logP	1.8	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	7.8	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	253.13 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	138.53 m³·mol⁻¹	ChemAxon
Polarizability	55.28 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

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

85278055

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4,5-dihydroxy-6-[2-(hydroxymethyl)phenoxy]-2-[(3,4,5-trihydroxybenzoyloxy)methyl]oxan-3-yl 3,4,5-trihydroxybenzoate (NP0325433)

MOL for NP0325433 (4,5-dihydroxy-6-[2-(hydroxymethyl)phenoxy]-2-[(3,4,5-trihydroxybenzoyloxy)methyl]oxan-3-yl 3,4,5-trihydroxybenzoate)

3D MOL for NP0325433 (4,5-dihydroxy-6-[2-(hydroxymethyl)phenoxy]-2-[(3,4,5-trihydroxybenzoyloxy)methyl]oxan-3-yl 3,4,5-trihydroxybenzoate)

3D SDF for NP0325433 (4,5-dihydroxy-6-[2-(hydroxymethyl)phenoxy]-2-[(3,4,5-trihydroxybenzoyloxy)methyl]oxan-3-yl 3,4,5-trihydroxybenzoate)

3D-SDF for NP0325433 (4,5-dihydroxy-6-[2-(hydroxymethyl)phenoxy]-2-[(3,4,5-trihydroxybenzoyloxy)methyl]oxan-3-yl 3,4,5-trihydroxybenzoate)

PDB for NP0325433 (4,5-dihydroxy-6-[2-(hydroxymethyl)phenoxy]-2-[(3,4,5-trihydroxybenzoyloxy)methyl]oxan-3-yl 3,4,5-trihydroxybenzoate)

3D PDB for NP0325433 (4,5-dihydroxy-6-[2-(hydroxymethyl)phenoxy]-2-[(3,4,5-trihydroxybenzoyloxy)methyl]oxan-3-yl 3,4,5-trihydroxybenzoate)

SMILES for NP0325433 (4,5-dihydroxy-6-[2-(hydroxymethyl)phenoxy]-2-[(3,4,5-trihydroxybenzoyloxy)methyl]oxan-3-yl 3,4,5-trihydroxybenzoate)

INCHI for NP0325433 (4,5-dihydroxy-6-[2-(hydroxymethyl)phenoxy]-2-[(3,4,5-trihydroxybenzoyloxy)methyl]oxan-3-yl 3,4,5-trihydroxybenzoate)

Structure for NP0325433 (4,5-dihydroxy-6-[2-(hydroxymethyl)phenoxy]-2-[(3,4,5-trihydroxybenzoyloxy)methyl]oxan-3-yl 3,4,5-trihydroxybenzoate)

3D Structure for NP0325433 (4,5-dihydroxy-6-[2-(hydroxymethyl)phenoxy]-2-[(3,4,5-trihydroxybenzoyloxy)methyl]oxan-3-yl 3,4,5-trihydroxybenzoate)